Reference/PubChem-compound 6140
type: UnificationXref
id: 6140
db: PubChem-compound

Reference/CAS 63-91-2
type: UnificationXref
id: 63-91-2
db: CAS

Sinapine
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00933
xref: Reference/ChemSpider 80576
xref: Reference/CAS 18696-26-9
xref: Reference/PubChem-compound 89287
xref: Reference/HMDB HMDB0029379
xref: Reference/ChEBI CHEBI 16353
chemical formula: C16H24NO5
molecular weight: 310.16544
structure: ChemicalStructure/PW C010625

Reference/ChEBI CHEBI 30797
type: UnificationXref
id: CHEBI:30797
db: ChEBI

Compound/PW C016451 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: 3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid
stoichiometric coefficient: 1.0

Coniferin
type: SmallMoleculeReference
xref: Reference/ChemSpider 4444067
xref: Reference/PubChem-compound 5280372
xref: Reference/CAS 531-29-3
xref: Reference/ChEBI CHEBI 16220
xref: Reference/HMDB HMDB0013682
xref: Reference/KEGG Compound C00761
chemical formula: C16H22O8
molecular weight: 342.13147
structure: ChemicalStructure/PW C008558

Reference/ChEBI CHEBI 87449
type: UnificationXref
id: CHEBI:87449
db: ChEBI

Reference/ChemSpider 50
type: UnificationXref
id: 50
db: ChemSpider

Reference/ChEBI CHEBI 16027
type: UnificationXref
id: CHEBI:16027
db: ChEBI

Cinnamyl alcohol dehydrogenase 5
type: ProteinReference
xref: Reference/UniProt O49482
organism: Arabidopsis thaliana

Cinnamyl alcohol dehydrogenase 4
type: ProteinReference
xref: Reference/UniProt P48523
organism: Arabidopsis thaliana

Reference/ChEBI CHEBI 139533
type: UnificationXref
id: CHEBI:139533
db: ChEBI

Ammonium
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0041827
xref: Reference/CAS 14798-03-9
xref: Reference/PubChem-compound 16741146
xref: Reference/KEGG Compound C01342
xref: Reference/ChEBI CHEBI 28938
xref: Reference/ChemSpider 218
chemical formula: H4N
molecular weight: 18.034374
structure: ChemicalStructure/PW C022608

Caffeoylshikimate esterase
type: ProteinReference
xref: Reference/UniProt Q9C942
organism: Arabidopsis thaliana

Reference/PubChem-compound 445858
type: UnificationXref
id: 445858
db: PubChem-compound

Reference/ChemSpider 559142
type: UnificationXref
id: 559142
db: ChemSpider

Compound/PW C001769 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Shikimic acid
stoichiometric coefficient: 1.0

Reference/CAS 530-59-6 7362-37-0
type: UnificationXref
id: 530-59-6 7362-37-0
db: CAS

Compound/PW C008119 Nucleus/Stoichiometry/1.0
type: Stoichiometry
physical entity: Coniferyl alcohol
stoichiometric coefficient: 1.0

Reference/UniProt Q9LVF0
type: UnificationXref
id: Q9LVF0
db: UniProt

Reference/ChemSpider 5742
type: UnificationXref
id: 5742
db: ChemSpider

Feruloyl CoA ortho-hydroxylase 2
type: ProteinReference
xref: Reference/UniProt Q9C899
organism: Arabidopsis thaliana

Reference/ChEBI CHEBI 16474
type: UnificationXref
id: CHEBI:16474
db: ChEBI

Syringyl lignin
type: SmallMolecule
cellular location: Extracellular Space
entity reference: Syringyl lignin

Aldehyde dehydrogenase family 2 member C4
type: ProteinReference
xref: Reference/UniProt Q56YU0
organism: Arabidopsis thaliana

Cytochrome P450 84A1
type: ProteinReference
xref: Reference/UniProt Q42600
organism: Arabidopsis thaliana

Compound/PW C008558 Nucleus/Stoichiometry/1.0
type: Stoichiometry
physical entity: Coniferin
stoichiometric coefficient: 1.0

trans-Cinnamic acid
type: SmallMolecule
cellular location: Cytosol
entity reference: trans-Cinnamic acid
name: SubPathwayOutput

Reference/CAS 97-67-6
type: UnificationXref
id: 97-67-6
db: CAS

ReactionCatalysis202506
type: Catalysis
controller: Feruloyl CoA ortho-hydroxylase 2
controlled: 1.14.11.61
control type: ACTIVATION

3,4-Dihydroxy-trans-cinnamate
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0003501
xref: Reference/ChEBI CHEBI 16433
xref: Reference/BioCyc CPD-676
xref: Reference/CAS 331-39-5
xref: Reference/PubChem-compound 689043
xref: Reference/KEGG Compound C01197
xref: Reference/ChemSpider 600426
chemical formula: C9H8O4
molecular weight: 180.04225
structure: ChemicalStructure/PW C001907

Reference/KEGG Compound C02646
type: UnificationXref
id: C02646
db: KEGG Compound

Shikimic acid
type: SmallMolecule
cellular location: Membrane
entity reference: Shikimic acid

ReactionCatalysis202502
type: Catalysis
controller: Quercetin 3'-O-methyltransferase
controlled: Reaction212869
control type: ACTIVATION

Reference/PubChem-compound 53477679
type: UnificationXref
id: 53477679
db: PubChem-compound

Reference/CAS 196496-50-1
type: UnificationXref
id: 196496-50-1
db: CAS

ReactionCatalysis202505
type: Catalysis
controller: Aldehyde dehydrogenase family 2 member C4
controlled: Reaction212870
control type: ACTIVATION

Reference/ChemSpider 1405788
type: UnificationXref
id: 1405788
db: ChemSpider

Compound/PW C000761 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: trans-Ferulic acid
stoichiometric coefficient: 1.0

ReactionCatalysis202500
type: Catalysis
controller: Cinnamyl alcohol dehydrogenase
controlled: Reaction212867
control type: ACTIVATION

ReactionCatalysis202501
type: Catalysis
controller: Quercetin 3'-O-methyltransferase
controlled: Reaction212868
control type: ACTIVATION

Reference/KEGG Compound C02887
type: UnificationXref
id: C02887
db: KEGG Compound

p-Coumaraldehyde
type: SmallMolecule
cellular location: Cytosol
entity reference: p-Coumaraldehyde

Reference/KEGG Compound C00223
type: UnificationXref
id: C00223
db: KEGG Compound

Compound/PW C000077 Plant-Type Vacuole/Stoichiometry/1.0
type: Stoichiometry
physical entity: D-Glucose
stoichiometric coefficient: 1.0

ChemicalStructure/PW C001099
type: ChemicalStructure
structure format: SMILES

Reference/KEGG Compound C12208
type: UnificationXref
id: C12208
db: KEGG Compound

Compound/PW C000761 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: trans-Ferulic acid
stoichiometric coefficient: 1.0

Reference/KEGG Compound C12205
type: UnificationXref
id: C12205
db: KEGG Compound

Reference/KEGG Compound C12206
type: UnificationXref
id: C12206
db: KEGG Compound

Reference/HMDB HMDB0013070
type: UnificationXref
id: HMDB0013070
db: HMDB

Cinnamoyl-CoA reductase 1
type: Protein
cellular location: Cytosol
entity reference: Cinnamoyl-CoA reductase 1

Reference/UniProt O49482
type: UnificationXref
id: O49482
db: UniProt

Reference/KEGG Compound C12203
type: UnificationXref
id: C12203
db: KEGG Compound

Reference/KEGG Compound C12204
type: UnificationXref
id: C12204
db: KEGG Compound

Reference/UniProt P0DI10
type: UnificationXref
id: P0DI10
db: UniProt

Compound/PW C000146/Stoichiometry/1.0
type: Stoichiometry
physical entity: NADPH
stoichiometric coefficient: 1.0

Peroxidase 1
type: Protein
cellular location: Nucleus
entity reference: Peroxidase 1

Hydrogen Ion
type: SmallMolecule
entity reference: Hydrogen Ion

Reference/CAS 979-92-0
type: UnificationXref
id: 979-92-0
db: CAS

Compound/PW C001795 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Chlorogenic acid
stoichiometric coefficient: 1.0

Reference/PathWhiz PW123946
type: UnificationXref
id: PW123946
db: PathWhiz

Cinnamoyl-CoA reductase 1
type: ProteinReference
xref: Reference/UniProt Q9S9N9

Peroxidase 1
type: ProteinReference
xref: Reference/UniProt P0DI10
organism: Arabidopsis thaliana

Reference/BioCyc SUC
type: UnificationXref
id: SUC
db: BioCyc

Caffeyl alcohol
type: SmallMolecule
cellular location: Cytosol
entity reference: Caffeyl alcohol

4-coumarate--CoA ligase 1
type: ProteinReference
xref: Reference/UniProt Q42524
organism: Arabidopsis thaliana

Coniferyl alcohol
type: SmallMoleculeReference
xref: Reference/PubChem-compound 1549095
xref: Reference/CAS 32811-40-8 458-35-5
xref: Reference/KEGG Compound C00590
xref: Reference/ChEBI CHEBI 17745
xref: Reference/BioCyc 5-HYDROXY-CONIFERYL-ALCOHOL
xref: Reference/ChemSpider 1266063
xref: Reference/HMDB HMDB0012915
chemical formula: C10H12O3
molecular weight: 180.07864
structure: ChemicalStructure/PW C008119

Reference/CAS 531-29-3
type: UnificationXref
id: 531-29-3
db: CAS

Reference/UniProt O49499
type: UnificationXref
id: O49499
db: UniProt

Compound/PW C000193 Nucleus/Stoichiometry/1.0
type: Stoichiometry
physical entity: Uridine diphosphate glucose
stoichiometric coefficient: 1.0

ChemicalStructure/PW C001907
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)\C=C/C1=CC(O)=C(O)C=C1

Reference/KEGG Compound C00007
type: UnificationXref
id: C00007
db: KEGG Compound

Reference/KEGG Compound C00006
type: UnificationXref
id: C00006
db: KEGG Compound

Reference/ChEBI CHEBI 18009
type: UnificationXref
id: CHEBI:18009
db: ChEBI

Hydrogen Ion
type: SmallMolecule
cellular location: Cytosol
entity reference: Hydrogen Ion

Reference/BioCyc CAFFEOYL-COA
type: UnificationXref
id: CAFFEOYL-COA
db: BioCyc

Reference/KEGG Compound C00001
type: UnificationXref
id: C00001
db: KEGG Compound

Reference/UniProt Q9CA61
type: UnificationXref
id: Q9CA61
db: UniProt

Reference/PubChem-compound 1794427
type: UnificationXref
id: 1794427
db: PubChem-compound

Reference/KEGG Compound C00482
type: UnificationXref
id: C00482
db: KEGG Compound

Reference/KEGG Compound C00005
type: UnificationXref
id: C00005
db: KEGG Compound

NADPH
type: SmallMolecule
cellular location: Cytosol
entity reference: NADPH

Reference/KEGG Compound C00002
type: UnificationXref
id: C00002
db: KEGG Compound

Compound/PW C000201 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Uridine 5'-diphosphate
stoichiometric coefficient: 1.0

Compound/PW C008119 Extracellular Space/Stoichiometry/1.0
type: Stoichiometry
physical entity: Coniferyl alcohol
stoichiometric coefficient: 1.0

ReactionCatalysis202539
type: Catalysis
controller: Tapetum-specific methyltransferase 1
controlled: 2.1.1.-
control type: ACTIVATION

Reference/KEGG Compound C00019
type: UnificationXref
id: C00019
db: KEGG Compound

Tapetum-specific methyltransferase 1
type: Protein
cellular location: Cytosol
entity reference: Tapetum-specific methyltransferase 1

Coenzyme A
type: SmallMolecule
cellular location: Cytosol
entity reference: Coenzyme A

ReactionCatalysis202535
type: Catalysis
controller: Peroxidase 1
controlled: Reaction212899
control type: ACTIVATION

ReactionCatalysis202536
type: Catalysis
controller: Cytochrome P450 98A8
controlled: 1.14.-.-
control type: ACTIVATION

ReactionCatalysis202537
type: Catalysis
controller: Unknown
controlled: 5.4.99.-
control type: ACTIVATION

ReactionCatalysis202538
type: Catalysis
controller: Cytochrome P450 98A8
controlled: Reaction212903
control type: ACTIVATION

Reference/KEGG Compound C01342
type: UnificationXref
id: C01342
db: KEGG Compound

Reference/KEGG Compound C00011
type: UnificationXref
id: C00011
db: KEGG Compound

ReactionCatalysis202532
type: Catalysis
controller: Peroxidase 1
controlled: Reaction212896
control type: ACTIVATION

Reference/KEGG Compound C00010
type: UnificationXref
id: C00010
db: KEGG Compound

ReactionCatalysis202533
type: Catalysis
controller: Peroxidase 1
controlled: Reaction212897
control type: ACTIVATION

Reference/KEGG Compound C00493
type: UnificationXref
id: C00493
db: KEGG Compound

ReactionCatalysis202534
type: Catalysis
controller: Peroxidase 1
controlled: Reaction212898
control type: ACTIVATION

Reference/KEGG Compound C00015
type: UnificationXref
id: C00015
db: KEGG Compound

Reference/KEGG Compound C00013
type: UnificationXref
id: C00013
db: KEGG Compound

Reference/UniProt P92994
type: UnificationXref
id: P92994
db: UniProt

Reference/PubChem-compound 444539
type: UnificationXref
id: 444539
db: PubChem-compound

Unknown
type: ProteinReference
organism: Arabidopsis thaliana

Reference/HMDB HMDB0032616
type: UnificationXref
id: HMDB0032616
db: HMDB

Hydrogen Ion
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00080
xref: Reference/ChEBI CHEBI 15378
xref: Reference/HMDB HMDB0059597
xref: Reference/PubChem-compound 1038
xref: Reference/ChemSpider 1010
chemical formula: H
molecular weight: 1.007825
structure: ChemicalStructure/PW C040034

4-Coumaryl alcohol
type: SmallMoleculeReference
xref: Reference/PubChem-compound 5280535
xref: Reference/ChemSpider 4444166
xref: Reference/HMDB HMDB0003654
xref: Reference/KEGG Compound C02646
xref: Reference/CAS 3690-05-9
xref: Reference/ChEBI CHEBI 64555
chemical formula: C9H10O2
molecular weight: 150.06808
structure: ChemicalStructure/PW C001949

Reference/KEGG Compound C00029
type: UnificationXref
id: C00029
db: KEGG Compound

Cytochrome P450 84A1
type: Protein
cellular location: Membrane
entity reference: Cytochrome P450 84A1

Reference/PubChem-compound 689043
type: UnificationXref
id: 689043
db: PubChem-compound

Reference/HMDB HMDB0003070
type: UnificationXref
id: HMDB0003070
db: HMDB

ReactionCatalysis202542
type: Catalysis
controller: UDP-glycosyltransferase 72E3
controlled: Reaction212907
control type: ACTIVATION

ReactionCatalysis202543
type: Catalysis
controller: UDP-glycosyltransferase 84A2
controlled: 2.4.1.120
control type: ACTIVATION

Reference/CAS 56-65-5
type: UnificationXref
id: 56-65-5
db: CAS

Reference/KEGG Compound C00021
type: UnificationXref
id: C00021
db: KEGG Compound

ReactionCatalysis202544
type: Catalysis
controller: Serine carboxypeptidase-like 8
controlled: 2.3.1.92,2.3.1.103
control type: ACTIVATION

Reference/KEGG Compound C00020
type: UnificationXref
id: C00020
db: KEGG Compound

ReactionCatalysis202545
type: Catalysis
controller: Serine carboxypeptidase-like 19
controlled: 2.3.1.91
control type: ACTIVATION

Coumaroyl-CoA
type: SmallMolecule
cellular location: Membrane
entity reference: Coumaroyl-CoA

5-O-Caffeoylshikimic acid
type: SmallMolecule
cellular location: Membrane
entity reference: 5-O-Caffeoylshikimic acid

Reference/KEGG Compound C00026
type: UnificationXref
id: C00026
db: KEGG Compound

ReactionCatalysis202540
type: Catalysis
controller: UDP-glycosyltransferase 72E3
controlled: 2.4.1.111,2.4.1.126
control type: ACTIVATION

ReactionCatalysis202541
type: Catalysis
controller: UDP-glycosyltransferase 72E3
controlled: Reaction212906
control type: ACTIVATION

Quinate
type: SmallMolecule
cellular location: Cytosol
entity reference: Quinate

Reference/KEGG Compound C00411
type: UnificationXref
id: C00411
db: KEGG Compound

Compound/PW C108931/Stoichiometry/1.0
type: Stoichiometry
physical entity: 6-Hydroxyferuloyl-CoA
stoichiometric coefficient: 1.0

NADP
type: SmallMolecule
cellular location: Cytosol
entity reference: NADP

Reference/ChEBI CHEBI 64557
type: UnificationXref
id: CHEBI:64557
db: ChEBI

Reference/ChEBI CHEBI 64555
type: UnificationXref
id: CHEBI:64555
db: ChEBI

Compound/PW C104780 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: p-Coumaroyl quinic acid
stoichiometric coefficient: 1.0

Feruloyl-CoA
type: SmallMoleculeReference
xref: Reference/BioCyc FERULOYL-COA
xref: Reference/ChEBI CHEBI 15511
xref: Reference/KEGG Compound C00406
xref: Reference/CAS 142185-30-6
xref: Reference/PubChem-compound 11966129
xref: Reference/ChemSpider 10140123
chemical formula: C31H44N7O19P3S
molecular weight: 943.16254
structure: ChemicalStructure/PW C096923

Caffeoyl-CoA
type: SmallMoleculeReference
xref: Reference/CAS 1021913-49-4
xref: Reference/BioCyc CAFFEOYL-COA
xref: Reference/PubChem-compound 11966126
xref: Reference/ChEBI CHEBI 87449
xref: Reference/KEGG Compound C00323
xref: Reference/ChemSpider 10140120
chemical formula: C30H42N7O19P3S
molecular weight: 929.1469
structure: ChemicalStructure/PW C096922

Cinnamoyl-CoA
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00540
xref: Reference/PubChem-compound 6444037
xref: Reference/CAS 30801-99-1
xref: Reference/ChEBI CHEBI 15463
xref: Reference/ChemSpider 21864782
chemical formula: C30H42N7O17P3S
molecular weight: 897.1571
structure: ChemicalStructure/PW C096925

4-Coumaroylshikimic acid
type: SmallMoleculeReference
xref: Reference/KEGG Compound C02947
xref: Reference/PubChem-compound 5280555
xref: Reference/BioCyc CPD-412
xref: Reference/CAS 196496-50-1
xref: Reference/ChEBI CHEBI 16428
xref: Reference/ChemSpider 4444183
chemical formula: C16H16O7
molecular weight: 320.0896
structure: ChemicalStructure/PW C096924

Reference/KEGG Compound C00031
type: UnificationXref
id: C00031
db: KEGG Compound

4-Coumaryl alcohol
type: SmallMolecule
cellular location: Nucleus
entity reference: 4-Coumaryl alcohol

Reference/HMDB HMDB0013682
type: UnificationXref
id: HMDB0013682
db: HMDB

Compound/PW C108953 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: N1,N5,N10-Triferuloyl spermidine
stoichiometric coefficient: 1.0

ChemicalStructure/PW C000174
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)CCC(O)=O

Reaction180294
type: BiochemicalReaction
participant stoichiometry: Compound/Generic302 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000742 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/Generic303 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001366 Membrane/Stoichiometry/1.0
right: 4-Hydroxycinnamic acid
right: [Oxidized NADPH---hemoprotein reductase]
right: Water
spontaneous: false
left: Oxygen
left: trans-Cinnamic acid
left: [Reduced NADPH---hemoprotein reductase]
name: Oxygen + [Reduced NADPH---hemoprotein reductase] + trans-Cinnamic acid → 4-Hydroxycinnamic acid + Water + [Oxidized NADPH---hemoprotein reductase]
conversion direction: LEFT_TO_RIGHT

ChemicalStructure/PW C000170
type: ChemicalStructure
structure format: SMILES
structure data: OP(O)(=O)OP(O)(O)=O

Phenylpropanoid Biosynthesis
type: Pathway
pathway order: PathwayEnzymeReaction/2460781
pathway order: PathwayEnzymeReaction/2460782
pathway order: PathwayEnzymeReaction/2460780
pathway order: PathwayTransport/2460961
pathway order: PathwayTransport/2460962
pathway order: PathwayEnzymeReaction/2460789
pathway order: PathwayEnzymeReaction/2460787
pathway order: PathwayEnzymeReaction/2460788
pathway order: PathwayEnzymeReaction/2460821
pathway order: PathwayEnzymeReaction/2460785
pathway order: PathwayEnzymeReaction/2460786
pathway order: PathwayEnzymeReaction/2460863
pathway order: PathwayEnzymeReaction/2460783
pathway order: PathwayEnzymeReaction/2460815
pathway order: PathwayTransport/2460967
pathway order: PathwayEnzymeReaction/2460792
pathway order: PathwayEnzymeReaction/2460793
pathway order: PathwayEnzymeReaction/2460790
pathway order: PathwaySubPathway/112788
pathway order: PathwayEnzymeReaction/2460791
pathway order: PathwaySubPathway/112789
pathway order: PathwayEnzymeReaction/2460833
pathway order: PathwayEnzymeReaction/2460954
pathway order: PathwayTransport/2461120
pathway order: PathwayEnzymeReaction/2460952
pathway order: PathwayTransport/2461122
pathway order: PathwayEnzymeReaction/2460832
pathway order: PathwayEnzymeReaction/2460953
pathway order: PathwayTransport/2461123
pathway order: PathwayEnzymeReaction/2460796
pathway order: PathwayEnzymeReaction/2460950
pathway order: PathwayEnzymeReaction/2460830
pathway order: PathwayEnzymeReaction/2460951
pathway order: PathwayEnzymeReaction/2460794
pathway order: PathwayEnzymeReaction/2460795
pathway order: PathwayEnzymeReaction/2460828
pathway order: PathwayEnzymeReaction/2460949
pathway order: PathwayEnzymeReaction/2460829
pathway order: PathwayEnzymeReaction/2460826
pathway order: PathwayEnzymeReaction/2460947
pathway order: PathwayEnzymeReaction/2460827
pathway order: PathwayEnzymeReaction/2460948
pathway order: PathwayEnzymeReaction/2460946
pathway order: PathwaySubPathway/112790
pathway order: PathwaySubPathway/112791
pathway order: PathwayTransport/2461118
pathway order: PathwayTransport/2461119
pathway order: PathwayTransport/2461116
pathway order: PathwayEnzymeReaction/2460767
pathway order: PathwayEnzymeReaction/2460844
pathway order: PathwayEnzymeReaction/2460965
pathway order: PathwayEnzymeReaction/2460842
pathway order: PathwayEnzymeReaction/2460843
pathway order: PathwayEnzymeReaction/2460840
pathway order: PathwayEnzymeReaction/2460841
pathway order: PathwayEnzymeReaction/2460839
pathway order: PathwayEnzymeReaction/2460879
pathway order: PathwayEnzymeReaction/2460836
pathway order: PathwayEnzymeReaction/2460811
pathway order: PathwayEnzymeReaction/2460975
pathway order: PathwayEnzymeReaction/2460774
pathway order: PathwayEnzymeReaction/2460972
pathway order: PathwayEnzymeReaction/2460970
pathway order: PathwayEnzymeReaction/2460971
pathway order: PathwayEnzymeReaction/2460806
pathway order: PathwayEnzymeReaction/2460807
pathway order: PathwayEnzymeReaction/2460804
pathway order: PathwayEnzymeReaction/2460805
pathway order: PathwayEnzymeReaction/2460802
pathway order: PathwayEnzymeReaction/2460803
pathway order: PathwayEnzymeReaction/2460968
pathway component: Reaction212896
pathway component: Reaction212897
pathway component: Reaction212898
pathway component: Reaction212899
pathway component: 2.3.1.133
pathway component: ReactionCatalysis202472
pathway component: ReactionCatalysis202473

Reference/BioCyc FERULOYL-COA
type: UnificationXref
id: FERULOYL-COA
db: BioCyc

Coniferyl aldehyde
type: SmallMolecule
cellular location: Membrane
entity reference: Coniferyl aldehyde

Reference/KEGG Compound C00042
type: UnificationXref
id: C00042
db: KEGG Compound

Shikimic acid
type: SmallMoleculeReference
xref: Reference/CAS 138-59-0
xref: Reference/HMDB HMDB0003070
xref: Reference/BioCyc 3-DEHYDRO-SHIKIMATE
xref: Reference/ChEBI CHEBI 16119
xref: Reference/KEGG Compound C00493
xref: Reference/ChemSpider 8412
xref: Reference/PubChem-compound 8742
chemical formula: C7H10O5
molecular weight: 174.05283
structure: ChemicalStructure/PW C001769

Compound/PW C001949 Nucleus/Stoichiometry/1.0
type: Stoichiometry
physical entity: 4-Coumaryl alcohol
stoichiometric coefficient: 1.0

Reference/HMDB HMDB0003654
type: UnificationXref
id: HMDB0003654
db: HMDB

Compound/PW C000193 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Uridine diphosphate glucose
stoichiometric coefficient: 1.0

Reference/PubChem-compound 3701
type: UnificationXref
id: 3701
db: PubChem-compound

p-Hydroxyphenyl lignin
type: SmallMolecule
cellular location: Nucleus
entity reference: p-Hydroxyphenyl lignin

Uridine 5'-diphosphate
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 17659
xref: Reference/PubChem-compound 6031
xref: Reference/CAS 58-98-0
xref: Reference/HMDB HMDB0000295
xref: Reference/KEGG Compound C00015
xref: Reference/ChemSpider 5809
xref: Reference/BioCyc UDP
chemical formula: C9H14N2O12P2
molecular weight: 404.0022
structure: ChemicalStructure/PW C000201

Reference/CAS 17230-85-2
type: UnificationXref
id: 17230-85-2
db: CAS

Reference/ChemSpider 394087
type: UnificationXref
id: 394087
db: ChemSpider

L-Phenylalanine
type: SmallMolecule
cellular location: Cytosol
entity reference: L-Phenylalanine
name: SubPathwayOutput

Reference/PubChem-compound 305
type: UnificationXref
id: 305
db: PubChem-compound

Reference/KEGG Compound C00296
type: UnificationXref
id: C00296
db: KEGG Compound

Compound/PW C008119 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Coniferyl alcohol
stoichiometric coefficient: 1.0

Compound/PW C108952/Stoichiometry/1.0
type: Stoichiometry
physical entity: N1,N5,N10-Tricaffeoyl spermidine
stoichiometric coefficient: 1.0

Reference/HMDB HMDB0000156
type: UnificationXref
id: HMDB0000156
db: HMDB

Sinapic acid
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0032616
xref: Reference/PubChem-compound 637775
xref: Reference/ChEBI CHEBI 15714
xref: Reference/ChemSpider 553361
xref: Reference/KEGG Compound C00482
xref: Reference/CAS 530-59-6 7362-37-0
chemical formula: C11H12O5
molecular weight: 224.06847
structure: ChemicalStructure/PW C013713

Reference/HMDB HMDB0000159
type: UnificationXref
id: HMDB0000159
db: HMDB

p-Coumaroyl quinic acid
type: SmallMolecule
cellular location: Membrane
entity reference: p-Coumaroyl quinic acid

Reference/HMDB HMDB0035484
type: UnificationXref
id: HMDB0035484
db: HMDB

Cinnamoyl-CoA
type: SmallMolecule
entity reference: Cinnamoyl-CoA

Adenosine triphosphate
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 15422
xref: Reference/PubChem-compound 5957
xref: Reference/HMDB HMDB0000538
xref: Reference/CAS 56-65-5
xref: Reference/ChemSpider 5742
xref: Reference/BioCyc ATP
xref: Reference/KEGG Compound C00002
chemical formula: C10H16N5O13P3
molecular weight: 506.99576
structure: ChemicalStructure/PW C000414

Feruloyl-CoA
type: SmallMolecule
entity reference: Feruloyl-CoA

Compound/PW C000077 Extracellular Space/Stoichiometry/1.0
type: Stoichiometry
physical entity: D-Glucose
stoichiometric coefficient: 1.0

Reference/PubChem-compound 962
type: UnificationXref
id: 962
db: PubChem-compound

Reference/ChemSpider 31983
type: UnificationXref
id: 31983
db: ChemSpider

Compound/PW C108950 Extracellular Space/Stoichiometry/1.0
type: Stoichiometry
physical entity: Syringyl lignin
stoichiometric coefficient: 1.0

Peroxidase 1
type: Protein
cellular location: Extracellular Space
entity reference: Peroxidase 1

Reference/CAS 32811-40-8 458-35-5
type: UnificationXref
id: 32811-40-8 458-35-5
db: CAS

Cinnamoyl-CoA
type: SmallMolecule
cellular location: Membrane
entity reference: Cinnamoyl-CoA

Reference/CAS 58-98-0
type: UnificationXref
id: 58-98-0
db: CAS

Coniferyl aldehyde
type: SmallMolecule
cellular location: Cytosol
entity reference: Coniferyl aldehyde

Reference/CAS 7400-08-0
type: UnificationXref
id: 7400-08-0
db: CAS

Carbon dioxide
type: SmallMoleculeReference
xref: Reference/PubChem-compound 280
xref: Reference/ChEBI CHEBI 16526
xref: Reference/ChemSpider 274
xref: Reference/HMDB HMDB0001967
xref: Reference/CAS 124-38-9
xref: Reference/KEGG Compound C00011
chemical formula: CO2
molecular weight: 43.98983
structure: ChemicalStructure/PW C001316

Reference/KEGG Compound C00079
type: UnificationXref
id: C00079
db: KEGG Compound

Reference/KEGG Compound C00080
type: UnificationXref
id: C00080
db: KEGG Compound

ChemicalStructure/PW C001065
type: ChemicalStructure
structure format: SMILES
structure data: O=O

Sinapyl alcohol
type: SmallMoleculeReference
xref: Reference/ChemSpider 4444145
xref: Reference/CAS 537-33-7
xref: Reference/HMDB HMDB0013070
xref: Reference/BioCyc SINAPYL-ALCOHOL
xref: Reference/KEGG Compound C02325
xref: Reference/PubChem-compound 5280507
xref: Reference/ChEBI CHEBI 64557
chemical formula: C11H14O4
molecular weight: 210.0892
structure: ChemicalStructure/PW C008194

Reference/HMDB HMDB0002111
type: UnificationXref
id: HMDB0002111
db: HMDB

Reference/PubChem-compound 47205129
type: UnificationXref
id: 47205129
db: PubChem-compound

Reference/HMDB HMDB0003441
type: UnificationXref
id: HMDB0003441
db: HMDB

[Oxidized NADPH---hemoprotein reductase]
type: SmallMolecule
cellular location: Membrane
entity reference: [Oxidized NADPH---hemoprotein reductase]

Reference/ChemSpider 5910
type: UnificationXref
id: 5910
db: ChemSpider

Reference/KEGG Compound C01175
type: UnificationXref
id: C01175
db: KEGG Compound

Reference/ChEBI CHEBI 32374
type: UnificationXref
id: CHEBI:32374
db: ChEBI

Cinnamyl alcohol dehydrogenase 5
type: Protein
cellular location: Cytosol
entity reference: Cinnamyl alcohol dehydrogenase 5

Reference/PubChem-compound 47205132
type: UnificationXref
id: 47205132
db: PubChem-compound

Reference/PubChem-compound 47205131
type: UnificationXref
id: 47205131
db: PubChem-compound

Reference/PubChem-compound 47205130
type: UnificationXref
id: 47205130
db: PubChem-compound

Reference/ChEBI CHEBI 4167
type: UnificationXref
id: CHEBI:4167
db: ChEBI

Reference/BioCyc P-COUMAROYL-COA
type: UnificationXref
id: P-COUMAROYL-COA
db: BioCyc

Reference/PubChem-compound 644102
type: UnificationXref
id: 644102
db: PubChem-compound

Coniferyl alcohol
type: SmallMolecule
cellular location: Membrane
entity reference: Coniferyl alcohol

Reference/PubChem-compound 6444037
type: UnificationXref
id: 6444037
db: PubChem-compound

Reference/UniProt Q9C899
type: UnificationXref
id: Q9C899
db: UniProt

4-Coumaroylshikimic acid
type: SmallMolecule
cellular location: Cytosol
entity reference: 4-Coumaroylshikimic acid

ChemicalStructure/PW C000193
type: ChemicalStructure
structure format: SMILES

Nucleus
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0005634

Compound/PW C108954 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: N1,N5,N10-Tri(hydroxyferuloyl) spermidine
stoichiometric coefficient: 1.0

Compound/PW C000101 Plant-Type Vacuole/Stoichiometry/1.0
type: Stoichiometry
physical entity: L-Malic acid
stoichiometric coefficient: 1.0

Reference/PubChem-compound 977
type: UnificationXref
id: 977
db: PubChem-compound

5-Hydroxyconiferyl alcohol
type: SmallMolecule
cellular location: Membrane
entity reference: 5-Hydroxyconiferyl alcohol

Carbon dioxide
type: SmallMolecule
entity reference: Carbon dioxide

Reference/KEGG Compound C01197
type: UnificationXref
id: C01197
db: KEGG Compound

Reference/CAS 62-49-7
type: UnificationXref
id: 62-49-7
db: CAS

4-Coumaryl alcohol
type: SmallMolecule
cellular location: Extracellular Space
entity reference: 4-Coumaryl alcohol

Compound/PW C108909 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: 5-O-Caffeoylshikimic acid
stoichiometric coefficient: 1.0

Reference/GENE ONTOLOGY GO 0000325
type: UnificationXref
id: GO:0000325
db: GENE ONTOLOGY

N1,N5,N10-Tricoumaroyl spermidine
type: SmallMolecule
cellular location: Membrane
entity reference: N1,N5,N10-Tricoumaroyl spermidine

Chlorogenic acid
type: SmallMoleculeReference
xref: Reference/BioCyc CAFFEOYLQUINATE
xref: Reference/CAS 327-97-9 202650-88-2
xref: Reference/HMDB HMDB0003164
xref: Reference/ChemSpider 1405788
xref: Reference/PubChem-compound 1794427
xref: Reference/KEGG Compound C00852
xref: Reference/ChEBI CHEBI 16112
chemical formula: C16H18O9
molecular weight: 354.0951
structure: ChemicalStructure/PW C001795

Choline
type: SmallMolecule
cellular location: Extracellular Space
entity reference: Choline

Reference/UniProt Q56YU0
type: UnificationXref
id: Q56YU0
db: UniProt

Diphosphoric acid
type: SmallMolecule
cellular location: Cytosol
entity reference: Diphosphoric acid

Compound/PW C001769 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Shikimic acid
stoichiometric coefficient: 1.0

Reference/ChemSpider 17215925
type: UnificationXref
id: 17215925
db: ChemSpider

Reference/BioCyc CPD-412
type: UnificationXref
id: CPD-412
db: BioCyc

Reference/TAXONOMY 3702
type: UnificationXref
id: 3702
db: TAXONOMY

Reference/PubChem-compound 4402
type: UnificationXref
id: 4402
db: PubChem-compound

Reference/ChEBI CHEBI 27949
type: UnificationXref
id: CHEBI:27949
db: ChEBI

Reference/ChemSpider 553148
type: UnificationXref
id: 553148
db: ChemSpider

Adenosine monophosphate
type: SmallMolecule
cellular location: Cytosol
entity reference: Adenosine monophosphate

ChemicalStructure/PW C104780
type: ChemicalStructure
structure format: SMILES

4-Hydroxycinnamic acid
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00811
xref: Reference/CAS 7400-08-0
xref: Reference/PubChem-compound 637542
xref: Reference/BioCyc COUMARATE
xref: Reference/HMDB HMDB0002035
xref: Reference/ChemSpider 553148
xref: Reference/ChEBI CHEBI 32374
chemical formula: C9H8O3
molecular weight: 164.04735
structure: ChemicalStructure/PW C001366

Reference/ChEBI CHEBI 15714
type: UnificationXref
id: CHEBI:15714
db: ChEBI

Compound/PW C008194 Extracellular Space/Stoichiometry/1.0
type: Stoichiometry
physical entity: Sinapyl alcohol
stoichiometric coefficient: 1.0

Adenosine monophosphate
type: SmallMoleculeReference
xref: Reference/CAS 61-19-8
xref: Reference/ChemSpider 5858
xref: Reference/HMDB HMDB0000045
xref: Reference/BioCyc AMP
xref: Reference/ChEBI CHEBI 16027
xref: Reference/PubChem-compound 6083
xref: Reference/KEGG Compound C00020
chemical formula: C10H14N5O7P
molecular weight: 347.06308
structure: ChemicalStructure/PW C000032

ChemicalStructure/PW C108903
type: ChemicalStructure
structure format: SMILES
structure data: OC1=CC=C(\C=C\C=O)C=C1

Reference/ChemSpider 4444145
type: UnificationXref
id: 4444145
db: ChemSpider

Reaction212823
type: BiochemicalReaction
participant stoichiometry: Compound/PW C096925 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000414 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000742 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000032 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108886 Cytosol/Stoichiometry/1.0
right: Adenosine monophosphate
right: Diphosphoric acid
right: Cinnamoyl-CoA
spontaneous: false
left: Adenosine triphosphate
left: Coenzyme A
left: trans-Cinnamic acid
name: Adenosine triphosphate + Coenzyme A + trans-Cinnamic acid → Adenosine monophosphate + Cinnamoyl-CoA + Diphosphoric acid
conversion direction: LEFT_TO_RIGHT

Reaction212824
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000146/Stoichiometry/1.0
participant stoichiometry: Compound/PW C096925/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001099/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001890/Stoichiometry/1.0
right: Cinnamoyl-CoA
right: Hydrogen Ion
right: NADPH
spontaneous: false
left: Coenzyme A
left: NADP
left: Cinnamaldehyde
name: Cinnamaldehyde + Coenzyme A + NADP ← Cinnamoyl-CoA + Hydrogen Ion + NADPH
conversion direction: RIGHT_TO_LEFT

ChemicalStructure/PW C108909
type: ChemicalStructure
structure format: SMILES

Reference/HMDB HMDB0000538
type: UnificationXref
id: HMDB0000538
db: HMDB

Reference/ChEBI CHEBI \28353
type: UnificationXref
id: CHEBI:\28353
db: ChEBI

Compound/PW C013713 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Sinapic acid
stoichiometric coefficient: 1.0

Compound/PW C001907 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: 3,4-Dihydroxy-trans-cinnamate
stoichiometric coefficient: 1.0

Compound/PW C008194 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Sinapyl alcohol
stoichiometric coefficient: 1.0

Reference/PubChem-compound 6816
type: UnificationXref
id: 6816
db: PubChem-compound

Unknown
type: Protein
entity reference: Unknown

Reference/PubChem-compound 51
type: UnificationXref
id: 51
db: PubChem-compound

ChemicalStructure/PW C001795
type: ChemicalStructure
structure format: SMILES

Reference/KEGG Compound C03161
type: UnificationXref
id: C03161
db: KEGG Compound

ChemicalStructure/PW C108911
type: ChemicalStructure
structure format: SMILES
structure data: [H]\C(CO)=C(\[H])C1=CC(O)=C(O)C=C1

ChemicalStructure/PW C108910
type: ChemicalStructure
structure format: SMILES
structure data: [H]\C(C=O)=C(\[H])C1=CC(O)=C(O)C=C1

Reaction212828
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108903 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C041674 Cytosol/Stoichiometry/1.0
right: Coumaroyl-CoA
right: Hydrogen Ion
right: NADPH
spontaneous: false
left: Coenzyme A
left: p-Coumaraldehyde
left: NADP
name: Coenzyme A + NADP + p-Coumaraldehyde ← Coumaroyl-CoA + Hydrogen Ion + NADPH
conversion direction: RIGHT_TO_LEFT

1.1.1.195
type: BiochemicalReaction
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108903 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001949 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Cytosol/Stoichiometry/1.0
right: 4-Coumaryl alcohol
right: NADP
spontaneous: false
EC number: 1.1.1.195
left: Hydrogen Ion
left: p-Coumaraldehyde
left: NADPH
name: Hydrogen Ion + NADPH + p-Coumaraldehyde → 4-Coumaryl alcohol + NADP
conversion direction: LEFT_TO_RIGHT

Compound/PW C001907 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: 3,4-Dihydroxy-trans-cinnamate
stoichiometric coefficient: 1.0

5-Hydroxyconiferyl alcohol
type: SmallMolecule
cellular location: Cytosol
entity reference: 5-Hydroxyconiferyl alcohol

ChemicalStructure/PW C096923
type: ChemicalStructure
structure format: SMILES

ChemicalStructure/PW C096924
type: ChemicalStructure
structure format: SMILES

ChemicalStructure/PW C096925
type: ChemicalStructure
structure format: SMILES

Reaction212835
type: BiochemicalReaction
participant stoichiometry: Compound/Generic302 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/Generic303 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C096924 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108909 Membrane/Stoichiometry/1.0
right: [Oxidized NADPH---hemoprotein reductase]
right: 5-O-Caffeoylshikimic acid
right: Water
spontaneous: false
left: Oxygen
left: 4-Coumaroylshikimic acid
left: [Reduced NADPH---hemoprotein reductase]
name: 4-Coumaroylshikimic acid + Oxygen + [Reduced NADPH---hemoprotein reductase] → 5-O-Caffeoylshikimic acid + Water + [Oxidized NADPH---hemoprotein reductase]
conversion direction: LEFT_TO_RIGHT

Reaction212836
type: BiochemicalReaction
participant stoichiometry: Compound/PW C096922 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001769 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108909 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
right: Shikimic acid
right: Caffeoyl-CoA
spontaneous: false
left: 5-O-Caffeoylshikimic acid
left: Coenzyme A
name: 5-O-Caffeoylshikimic acid + Coenzyme A → Caffeoyl-CoA + Shikimic acid
conversion direction: LEFT_TO_RIGHT

ChemicalStructure/PW C096922
type: ChemicalStructure
structure format: SMILES

Reference/PubChem-compound 7932
type: UnificationXref
id: 7932
db: PubChem-compound

Reference/ChemSpider 274
type: UnificationXref
id: 274
db: ChemSpider

3.1.1.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001907 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108909 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001769 Membrane/Stoichiometry/1.0
right: Shikimic acid
right: 3,4-Dihydroxy-trans-cinnamate
spontaneous: false
EC number: 3.1.1.-
left: 5-O-Caffeoylshikimic acid
left: Water
name: 5-O-Caffeoylshikimic acid + Water → 3,4-Dihydroxy-trans-cinnamate + Shikimic acid
conversion direction: LEFT_TO_RIGHT

ChemicalStructure/PW C108922
type: ChemicalStructure
structure format: SMILES
structure data: COC1=CC(\C=C\C=O)=CC(O)=C1O

Reaction212838
type: BiochemicalReaction
participant stoichiometry: Compound/PW C096922 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000414 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000032 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108886 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001907 Cytosol/Stoichiometry/1.0
right: Adenosine monophosphate
right: Diphosphoric acid
right: Caffeoyl-CoA
spontaneous: false
left: Adenosine triphosphate
left: Coenzyme A
left: 3,4-Dihydroxy-trans-cinnamate
name: 3,4-Dihydroxy-trans-cinnamate + Adenosine triphosphate + Coenzyme A → Adenosine monophosphate + Caffeoyl-CoA + Diphosphoric acid
conversion direction: LEFT_TO_RIGHT

Reference/ChemSpider 393368
type: UnificationXref
id: 393368
db: ChemSpider

ChemicalStructure/PW C108921
type: ChemicalStructure
structure format: SMILES

Reference/ChEBI CHEBI 15937
type: UnificationXref
id: CHEBI:15937
db: ChEBI

2.1.1.42
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000749 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000761 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000921 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001907 Cytosol/Stoichiometry/1.0
right: S-Adenosylhomocysteine
right: trans-Ferulic acid
spontaneous: false
EC number: 2.1.1.42
left: 3,4-Dihydroxy-trans-cinnamate
left: S-Adenosylmethionine
name: 3,4-Dihydroxy-trans-cinnamate + S-Adenosylmethionine → S-Adenosylhomocysteine + trans-Ferulic acid
conversion direction: LEFT_TO_RIGHT

ChemicalStructure/PW C108920
type: ChemicalStructure
structure format: SMILES
structure data: [H]\C(C=O)=C(\[H])C1=CC(OC)=C(O)C=C1

ChemicalStructure/PW C108923
type: ChemicalStructure
structure format: SMILES
structure data: COC1=CC(\C=C\CO)=CC(O)=C1O

Reaction212840
type: BiochemicalReaction
participant stoichiometry: Compound/PW C096922 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108910 Cytosol/Stoichiometry/1.0
right: Hydrogen Ion
right: Caffeoyl-CoA
right: NADPH
spontaneous: false
left: Caffeic aldehyde
left: Coenzyme A
left: NADP
name: Caffeic aldehyde + Coenzyme A + NADP ← Caffeoyl-CoA + Hydrogen Ion + NADPH
conversion direction: RIGHT_TO_LEFT

ChemicalStructure/PW C108929
type: ChemicalStructure
structure format: SMILES
structure data: COC1=CC(\C=C\C=O)=CC(OC)=C1O

ChemicalStructure/PW C108928
type: ChemicalStructure
structure format: SMILES

Compound/PW C008119 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Coniferyl alcohol
stoichiometric coefficient: 1.0

Transport10813
type: Transport
participant stoichiometry: Compound/PW C008194 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008194 Extracellular Space/Stoichiometry/1.0
right: Sinapyl alcohol
spontaneous: false
left: Sinapyl alcohol
name: Sinapyl alcohol (→) Transport: Arabidopsis thaliana, Cell, Cytosol to Arabidopsis thaliana, Cell, Extracellular Space
conversion direction: LEFT_TO_RIGHT

Reference/KEGG Compound C00903
type: UnificationXref
id: C00903
db: KEGG Compound

[Reduced NADPH---hemoprotein reductase]
type: SmallMoleculeReference
xref: Reference/KEGG Compound C03024

Transport10814
type: Transport
participant stoichiometry: Compound/PW C108957 Plant-Type Vacuole/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108957 Cytosol/Stoichiometry/1.0
right: 1-O-Sinapoyl-beta-D-glucose
spontaneous: false
left: 1-O-Sinapoyl-beta-D-glucose
name: 1-O-Sinapoyl-beta-D-glucose (→) Transport: Arabidopsis thaliana, Cell, Cytosol to Arabidopsis thaliana, Cell, Plant-Type Vacuole
conversion direction: LEFT_TO_RIGHT

[Oxidized NADPH---hemoprotein reductase]
type: SmallMoleculeReference
xref: Reference/KEGG Compound C03161

Transport10815
type: Transport
participant stoichiometry: Compound/PW C108957 Extracellular Space/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108957 Cytosol/Stoichiometry/1.0
right: 1-O-Sinapoyl-beta-D-glucose
spontaneous: false
left: 1-O-Sinapoyl-beta-D-glucose
name: 1-O-Sinapoyl-beta-D-glucose (→) Transport: Arabidopsis thaliana, Cell, Cytosol to Arabidopsis thaliana, Cell, Extracellular Space
conversion direction: LEFT_TO_RIGHT

Pyrophosphate
type: SmallMolecule
cellular location: Cytosol
entity reference: Pyrophosphate

Reaction212847
type: BiochemicalReaction
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108911 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108910 Cytosol/Stoichiometry/1.0
right: Caffeyl alcohol
right: NADP
spontaneous: false
left: Caffeic aldehyde
left: Hydrogen Ion
left: NADPH
name: Caffeic aldehyde + Hydrogen Ion + NADPH → Caffeyl alcohol + NADP
conversion direction: LEFT_TO_RIGHT

Reference/ChEBI CHEBI 81480
type: UnificationXref
id: CHEBI:81480
db: ChEBI

Reference/CAS 485-80-3
type: UnificationXref
id: 485-80-3
db: CAS

Transport10810
type: Transport
participant stoichiometry: Compound/PW C001949 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001949 Nucleus/Stoichiometry/1.0
right: 4-Coumaryl alcohol
spontaneous: false
left: 4-Coumaryl alcohol
name: 4-Coumaryl alcohol (→) Transport: Arabidopsis thaliana, Cell, Cytosol to Arabidopsis thaliana, Cell, Nucleus
conversion direction: LEFT_TO_RIGHT

Transport10811
type: Transport
participant stoichiometry: Compound/PW C008194 Nucleus/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008194 Cytosol/Stoichiometry/1.0
right: Sinapyl alcohol
spontaneous: false
left: Sinapyl alcohol
name: Sinapyl alcohol (→) Transport: Arabidopsis thaliana, Cell, Cytosol to Arabidopsis thaliana, Cell, Nucleus
conversion direction: LEFT_TO_RIGHT

Transport10812
type: Transport
participant stoichiometry: Compound/PW C108923 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108923 Extracellular Space/Stoichiometry/1.0
right: 5-Hydroxyconiferyl alcohol
spontaneous: false
left: 5-Hydroxyconiferyl alcohol
name: 5-Hydroxyconiferyl alcohol (→) Transport: Arabidopsis thaliana, Cell, Cytosol to Arabidopsis thaliana, Cell, Extracellular Space
conversion direction: LEFT_TO_RIGHT

ChemicalStructure/PW C001769
type: ChemicalStructure
structure format: SMILES
structure data: O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O

D-Glucose
type: SmallMolecule
cellular location: Plant-Type Vacuole
entity reference: D-Glucose

Reference/CAS 327-97-9 202650-88-2
type: UnificationXref
id: 327-97-9 202650-88-2
db: CAS

Reference/KEGG Compound C10945
type: UnificationXref
id: C10945
db: KEGG Compound

ChemicalStructure/PW C000201
type: ChemicalStructure
structure format: SMILES

Reaction212848
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001949 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108911 Cytosol/Stoichiometry/1.0
right: Caffeyl alcohol
spontaneous: false
left: 4-Coumaryl alcohol
name: 4-Coumaryl alcohol → Caffeyl alcohol
conversion direction: LEFT_TO_RIGHT

Reaction212849
type: BiochemicalReaction
participant stoichiometry: Compound/PW C096923 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000761 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000414 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000032 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108886 Cytosol/Stoichiometry/1.0
right: Adenosine monophosphate
right: Feruloyl-CoA
right: Diphosphoric acid
spontaneous: false
left: Adenosine triphosphate
left: Coenzyme A
left: trans-Ferulic acid
name: Adenosine triphosphate + Coenzyme A + trans-Ferulic acid → Adenosine monophosphate + Diphosphoric acid + Feruloyl-CoA
conversion direction: LEFT_TO_RIGHT

ChemicalStructure/PW C108931
type: ChemicalStructure
structure format: SMILES

Reference/ChEBI CHEBI 81478
type: UnificationXref
id: CHEBI:81478
db: ChEBI

Reference/ChEBI CHEBI 81479
type: UnificationXref
id: CHEBI:81479
db: ChEBI

Reference/BioCyc NADPH
type: UnificationXref
id: NADPH
db: BioCyc

Transport10802
type: Transport
participant stoichiometry: Compound/PW C008119 Nucleus/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008119 Cytosol/Stoichiometry/1.0
right: Coniferyl alcohol
spontaneous: false
left: Coniferyl alcohol
name: Coniferyl alcohol (→) Transport: Arabidopsis thaliana, Cell, Cytosol to Arabidopsis thaliana, Cell, Nucleus
conversion direction: LEFT_TO_RIGHT

Reference/BioCyc CPD-6641
type: UnificationXref
id: CPD-6641
db: BioCyc

Compound/PW C108929 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Sinapoyl aldehyde
stoichiometric coefficient: 1.0

Reference/ChemSpider 218
type: UnificationXref
id: 218
db: ChemSpider

Reference/BioCyc UDP-GLUCOSE
type: UnificationXref
id: UDP-GLUCOSE
db: BioCyc

Reference/HMDB HMDB0001423
type: UnificationXref
id: HMDB0001423
db: HMDB

Compound/PW C044502 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Quinate
stoichiometric coefficient: 1.0

Feruloyl-CoA
type: SmallMolecule
cellular location: Cytosol
entity reference: Feruloyl-CoA

Reference/ChEBI CHEBI 30915
type: UnificationXref
id: CHEBI:30915
db: ChEBI

D-Glucose
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0000122
xref: Reference/PubChem-compound 5793
xref: Reference/CAS 2280-44-6
xref: Reference/ChemSpider 5589
xref: Reference/ChEBI CHEBI 4167
xref: Reference/BioCyc GLC
xref: Reference/KEGG Compound C00031
chemical formula: C6H12O6
molecular weight: 180.06339
structure: ChemicalStructure/PW C000077

Compound/PW C108951 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: N1,N5,N10-Tricoumaroyl spermidine
stoichiometric coefficient: 1.0

Reference/SMPDB SMP0122631
type: UnificationXref
id: SMP0122631
db: SMPDB

Reference/CAS 119785-99-8
type: UnificationXref
id: 119785-99-8
db: CAS

Sinapyl alcohol
type: SmallMolecule
cellular location: Nucleus
entity reference: Sinapyl alcohol

Reference/UniProt Q9C9W4
type: UnificationXref
id: Q9C9W4
db: UniProt

Reference/ChemSpider 4444183
type: UnificationXref
id: 4444183
db: ChemSpider

ChemicalStructure/PW C108951
type: ChemicalStructure
structure format: SMILES

ChemicalStructure/PW C108955
type: ChemicalStructure
structure format: SMILES

ChemicalStructure/PW C108954
type: ChemicalStructure
structure format: SMILES

ChemicalStructure/PW C108953
type: ChemicalStructure
structure format: SMILES

ChemicalStructure/PW C108952
type: ChemicalStructure
structure format: SMILES

ChemicalStructure/PW C108958
type: ChemicalStructure
structure format: SMILES

ChemicalStructure/PW C108957
type: ChemicalStructure
structure format: SMILES

ChemicalStructure/PW C108956
type: ChemicalStructure
structure format: SMILES

Compound/PW C096925 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Cinnamoyl-CoA
stoichiometric coefficient: 1.0

Reference/KEGG Compound C00933
type: UnificationXref
id: C00933
db: KEGG Compound

ChemicalStructure/PW C008194
type: ChemicalStructure
structure format: SMILES
structure data: COC1=CC(\C=C\CO)=CC(OC)=C1O

Reference/ChEBI CHEBI 15741
type: UnificationXref
id: CHEBI:15741
db: ChEBI

Reference/BioCyc CPD-676
type: UnificationXref
id: CPD-676
db: BioCyc

Reference/BioCyc CPD-674
type: UnificationXref
id: CPD-674
db: BioCyc

ChemicalStructure/PW C001316
type: ChemicalStructure
structure format: SMILES
structure data: O=C=O

N1,N5,N10-Tricoumaroyl spermidine
type: SmallMolecule
cellular location: Cytosol
entity reference: N1,N5,N10-Tricoumaroyl spermidine

Coniferyl alcohol
type: SmallMolecule
cellular location: Extracellular Space
entity reference: Coniferyl alcohol

Reference/PubChem-compound 1110
type: UnificationXref
id: 1110
db: PubChem-compound

Hydrogen Ion
type: SmallMolecule
cellular location: Membrane
entity reference: Hydrogen Ion

Plant-Type Vacuole
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0000325

Reference/PubChem-compound 5957
type: UnificationXref
id: 5957
db: PubChem-compound

Reference/ChemSpider 4444166
type: UnificationXref
id: 4444166
db: ChemSpider

Reference/ChEBI CHEBI 15511
type: UnificationXref
id: CHEBI:15511
db: ChEBI

Reference/UniProt Q42600
type: UnificationXref
id: Q42600
db: UniProt

Compound/PW C108909 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: 5-O-Caffeoylshikimic acid
stoichiometric coefficient: 1.0

Reference/KEGG Compound C10434
type: UnificationXref
id: C10434
db: KEGG Compound

Reference/CAS 30801-99-1
type: UnificationXref
id: 30801-99-1
db: CAS

Reference/HMDB HMDB0000122
type: UnificationXref
id: HMDB0000122
db: HMDB

Reference/UniProt Q94A18
type: UnificationXref
id: Q94A18
db: UniProt

Choline
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 15354
xref: Reference/ChemSpider 299
xref: Reference/BioCyc CPD-563
xref: Reference/PubChem-compound 305
xref: Reference/CAS 62-49-7
xref: Reference/HMDB HMDB0000097
xref: Reference/KEGG Compound C00114
chemical formula: C5H14NO
molecular weight: 104.10754
structure: ChemicalStructure/PW C000065

Reference/ChEBI CHEBI 17745
type: UnificationXref
id: CHEBI:17745
db: ChEBI

Reference/PubChem-compound 89287
type: UnificationXref
id: 89287
db: PubChem-compound

3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0035484
xref: Reference/KEGG Compound C05619
xref: Reference/CAS 2041-35-2
xref: Reference/PubChem-compound 446834
xref: Reference/ChemSpider 394087
chemical formula: C10H10O5
molecular weight: 210.05283
structure: ChemicalStructure/PW C016451

Reference/BioCyc UDP
type: UnificationXref
id: UDP
db: BioCyc

Compound/PW C096922 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Caffeoyl-CoA
stoichiometric coefficient: 1.0

Reference/HMDB HMDB0000930
type: UnificationXref
id: HMDB0000930
db: HMDB

4-Hydroxycinnamic acid
type: SmallMolecule
cellular location: Membrane
entity reference: 4-Hydroxycinnamic acid

Caffeoyl-CoA O-methyltransferase 1
type: ProteinReference
xref: Reference/UniProt O49499
organism: Arabidopsis thaliana

Compound/PW C000146 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: NADPH
stoichiometric coefficient: 1.0

Reference/CAS 14000-31-8
type: UnificationXref
id: 14000-31-8
db: CAS

D-Glucose
type: SmallMolecule
cellular location: Extracellular Space
entity reference: D-Glucose

TransportCatalysis1973
type: Catalysis
controller: ABC transporter G family member 29
controlled: Transport10797
control type: ACTIVATION

ChemicalStructure/PW C001949
type: ChemicalStructure
structure format: SMILES
structure data: OC\C=C\C1=CC=C(O)C=C1

TransportCatalysis1974
type: Catalysis
controller: Unknown
controlled: Transport10798
control type: ACTIVATION

Reference/BioCyc CO-A
type: UnificationXref
id: CO-A
db: BioCyc

Hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase
type: ProteinReference
xref: Reference/UniProt Q9FI78
organism: Arabidopsis thaliana

Reference/ChEBI CHEBI 16428
type: UnificationXref
id: CHEBI:16428
db: ChEBI

Cytochrome P450 98A3
type: ProteinReference
xref: Reference/UniProt O22203
organism: Arabidopsis thaliana

Reference/PubChem-compound 222656
type: UnificationXref
id: 222656
db: PubChem-compound

Reference/ChemSpider 5675
type: UnificationXref
id: 5675
db: ChemSpider

Reference/ChemSpider 1078
type: UnificationXref
id: 1078
db: ChemSpider

Reference/HMDB HMDB0000939
type: UnificationXref
id: HMDB0000939
db: HMDB

TransportCatalysis1978
type: Catalysis
controller: Unknown
controlled: Transport10802
control type: ACTIVATION

Reference/CAS 14798-03-9
type: UnificationXref
id: 14798-03-9
db: CAS

Compound/PW C108928 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Sinapoyl-CoA
stoichiometric coefficient: 1.0

Reference/HMDB HMDB0012915
type: UnificationXref
id: HMDB0012915
db: HMDB

Compound/PW C108921 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: 5-Hydroxyferuloyl-CoA
stoichiometric coefficient: 1.0

Compound/PW C108922 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: 5-Hydroxyconiferaldehyde
stoichiometric coefficient: 1.0

TransportCatalysis1984
type: Catalysis
controller: Unknown
controlled: Transport10810
control type: ACTIVATION

Coumaroyl-CoA
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0060153
xref: Reference/PubChem-compound 6440013
xref: Reference/ChEBI CHEBI 15499
xref: Reference/CAS 119785-99-8
xref: Reference/ChemSpider 21864784
xref: Reference/BioCyc P-COUMAROYL-COA
xref: Reference/KEGG Compound C00223
chemical formula: C30H42N7O18P3S
molecular weight: 913.152
structure: ChemicalStructure/PW C041674

TransportCatalysis1986
type: Catalysis
controller: Unknown
controlled: Transport10812
control type: ACTIVATION

TransportCatalysis1985
type: Catalysis
controller: Unknown
controlled: Transport10811
control type: ACTIVATION

Reference/UniProt P35510
type: UnificationXref
id: P35510
db: UniProt

Reference/ChemSpider 6557
type: UnificationXref
id: 6557
db: ChemSpider

TransportCatalysis1988
type: Catalysis
controller: Unknown
controlled: Transport10814
control type: ACTIVATION

TransportCatalysis1987
type: Catalysis
controller: Unknown
controlled: Transport10813
control type: ACTIVATION

Reference/ChEBI CHEBI 15540
type: UnificationXref
id: CHEBI:15540
db: ChEBI

TransportCatalysis1989
type: Catalysis
controller: Unknown
controlled: Transport10815
control type: ACTIVATION

Compound/PW C001316/Stoichiometry/1.0
type: Stoichiometry
physical entity: Carbon dioxide
stoichiometric coefficient: 1.0

ChemicalStructure/PW C008558
type: ChemicalStructure
structure format: SMILES

Reference/HMDB HMDB0000954
type: UnificationXref
id: HMDB0000954
db: HMDB

Reference/UniProt Q8VZU3
type: UnificationXref
id: Q8VZU3
db: UniProt

Syringin
type: SmallMolecule
cellular location: Nucleus
entity reference: Syringin

Reference/HMDB HMDB0029379
type: UnificationXref
id: HMDB0029379
db: HMDB

ChemicalStructure/PW C010625
type: ChemicalStructure
structure format: SMILES
structure data: COC1=CC(\C=C\C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O

Water
type: SmallMolecule
cellular location: Cytosol
entity reference: Water

ChemicalStructure/PW C022608
type: ChemicalStructure
structure format: SMILES
structure data: [NH4+]

Reference/ChemSpider 392447
type: UnificationXref
id: 392447
db: ChemSpider

Reference/PubChem-compound 641301
type: UnificationXref
id: 641301
db: PubChem-compound

Compound/PW C001099/Stoichiometry/1.0
type: Stoichiometry
physical entity: Coenzyme A
stoichiometric coefficient: 1.0

NADP
type: SmallMolecule
cellular location: Membrane
entity reference: NADP

Compound/PW C000134/Stoichiometry/1.0
type: Stoichiometry
physical entity: Oxoglutaric acid
stoichiometric coefficient: 1.0

Reference/CAS 7782-44-7
type: UnificationXref
id: 7782-44-7
db: CAS

Reference/GENE ONTOLOGY GO 0016020
type: UnificationXref
id: GO:0016020
db: GENE ONTOLOGY

5-Hydroxyconiferaldehyde
type: SmallMolecule
cellular location: Membrane
entity reference: 5-Hydroxyconiferaldehyde

Compound/PW C096925/Stoichiometry/1.0
type: Stoichiometry
physical entity: Cinnamoyl-CoA
stoichiometric coefficient: 1.0

Compound/PW C108954 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: N1,N5,N10-Tri(hydroxyferuloyl) spermidine
stoichiometric coefficient: 1.0

Reference/ChemSpider 10140123
type: UnificationXref
id: 10140123
db: ChemSpider

Compound/PW C001366 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: 4-Hydroxycinnamic acid
stoichiometric coefficient: 1.0

Reference/ChemSpider 10140120
type: UnificationXref
id: 10140120
db: ChemSpider

Compound/PW C008194 Nucleus/Stoichiometry/1.0
type: Stoichiometry
physical entity: Sinapyl alcohol
stoichiometric coefficient: 1.0

5-O-Caffeoylshikimic acid
type: SmallMolecule
cellular location: Cytosol
entity reference: 5-O-Caffeoylshikimic acid

Compound/PW C000742 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: trans-Cinnamic acid
stoichiometric coefficient: 1.0

Reference/BioCyc 2-KETOGLUTARATE
type: UnificationXref
id: 2-KETOGLUTARATE
db: BioCyc

Compound/PW C000174/Stoichiometry/1.0
type: Stoichiometry
physical entity: Succinic acid
stoichiometric coefficient: 1.0

Compound/PW C108923 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: 5-Hydroxyconiferyl alcohol
stoichiometric coefficient: 1.0

Reference/CAS 110-15-6
type: UnificationXref
id: 110-15-6
db: CAS

Reference/ChemSpider 299
type: UnificationXref
id: 299
db: ChemSpider

Compound/PW C001949 Extracellular Space/Stoichiometry/1.0
type: Stoichiometry
physical entity: 4-Coumaryl alcohol
stoichiometric coefficient: 1.0

ChemicalStructure/PW C013713
type: ChemicalStructure
structure format: SMILES
structure data: COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O

1-O-Sinapoyl-beta-D-glucose
type: SmallMolecule
cellular location: Extracellular Space
entity reference: 1-O-Sinapoyl-beta-D-glucose

[Reduced NADPH---hemoprotein reductase]
type: SmallMolecule
cellular location: Membrane
entity reference: [Reduced NADPH---hemoprotein reductase]

Reference/ChEBI CHEBI 15377
type: UnificationXref
id: CHEBI:15377
db: ChEBI

Reference/KEGG Compound C02947
type: UnificationXref
id: C02947
db: KEGG Compound

Reference/ChEBI CHEBI 15379
type: UnificationXref
id: CHEBI:15379
db: ChEBI

Reference/ChEBI CHEBI 15378
type: UnificationXref
id: CHEBI:15378
db: ChEBI

ChemicalStructure/PW C040034
type: ChemicalStructure
structure format: SMILES
structure data: [H+]

Reference/PubChem-compound 14350
type: UnificationXref
id: 14350
db: PubChem-compound

ChemicalStructure/PW C000414
type: ChemicalStructure
structure format: SMILES

ReactionCatalysis170247
type: Catalysis
controller: 4-coumarate--CoA ligase 1
controlled: 6.2.1.12
control type: ACTIVATION

Reference/PubChem-compound 14351
type: UnificationXref
id: 14351
db: PubChem-compound

Reference/PubChem-compound 14352
type: UnificationXref
id: 14352
db: PubChem-compound

Reference/ChemSpider 553117
type: UnificationXref
id: 553117
db: ChemSpider

Reference/ChEBI CHEBI 16220
type: UnificationXref
id: CHEBI:16220
db: ChEBI

Reference/KEGG Compound C00761
type: UnificationXref
id: C00761
db: KEGG Compound

Sinapoyl-CoA
type: SmallMolecule
cellular location: Cytosol
entity reference: Sinapoyl-CoA

4-Hydroxycinnamyl alcohol 4-D-glucoside
type: SmallMoleculeReference
xref: Reference/KEGG Compound C05855
chemical formula: C15H20O7
molecular weight: 312.1209
structure: ChemicalStructure/PW C104813

Compound/PW C010625 Extracellular Space/Stoichiometry/1.0
type: Stoichiometry
physical entity: Sinapine
stoichiometric coefficient: 1.0

Reference/ChEBI CHEBI 16433
type: UnificationXref
id: CHEBI:16433
db: ChEBI

Reference/PubChem-compound 5793
type: UnificationXref
id: 5793
db: PubChem-compound

Reference/PubChem-compound 14349
type: UnificationXref
id: 14349
db: PubChem-compound

Reference/KEGG Compound C18069
type: UnificationXref
id: C18069
db: KEGG Compound

Reference/ChemSpider 553361
type: UnificationXref
id: 553361
db: ChemSpider

ChemicalStructure/PW C008119
type: ChemicalStructure
structure format: SMILES
structure data: COC1=CC(\C=C\CO)=CC=C1O

Compound/PW C001099 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Coenzyme A
stoichiometric coefficient: 1.0

Cinnamyl alcohol dehydrogenase
type: Complex
cellular location: Cytosol
component: Cinnamyl alcohol dehydrogenase 5
component: Cinnamyl alcohol dehydrogenase 4

ReactionCatalysis170021
type: Catalysis
controller: Caffeoyl-CoA O-methyltransferase 1
controlled: Reaction180169
control type: ACTIVATION

Sinapyl alcohol
type: SmallMolecule
cellular location: Cytosol
entity reference: Sinapyl alcohol

Caffeic aldehyde
type: SmallMolecule
cellular location: Cytosol
entity reference: Caffeic aldehyde

ReactionCatalysis170023
type: Catalysis
controller: Hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase
controlled: 2.3.1.133
control type: ACTIVATION

ReactionCatalysis170025
type: Catalysis
controller: Cytochrome P450 98A3
controlled: 1.14.14.96
control type: ACTIVATION

Reference/UniProt O81498
type: UnificationXref
id: O81498
db: UniProt

Reference/ChEBI CHEBI 29751
type: UnificationXref
id: CHEBI:29751
db: ChEBI

Compound/PW C108920 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Coniferyl aldehyde
stoichiometric coefficient: 1.0

Reference/ChEBI CHEBI 15354
type: UnificationXref
id: CHEBI:15354
db: ChEBI

Reference/KEGG Compound C00540
type: UnificationXref
id: C00540
db: KEGG Compound

Reference/KEGG Compound C18071
type: UnificationXref
id: C18071
db: KEGG Compound

Reference/ChemSpider 1266063
type: UnificationXref
id: 1266063
db: ChemSpider

Reference/KEGG Compound C18070
type: UnificationXref
id: C18070
db: KEGG Compound

Reference/ChEBI CHEBI 16680
type: UnificationXref
id: CHEBI:16680
db: ChEBI

Reference/KEGG Compound C18072
type: UnificationXref
id: C18072
db: KEGG Compound

Reference/PubChem-compound 4695
type: UnificationXref
id: 4695
db: PubChem-compound

Reference/PubChem-compound 6440013
type: UnificationXref
id: 6440013
db: PubChem-compound

Reference/CAS 18696-26-9
type: UnificationXref
id: 18696-26-9
db: CAS

Reference/CAS 85-61-0
type: UnificationXref
id: 85-61-0
db: CAS

L-Malic acid
type: SmallMolecule
cellular location: Plant-Type Vacuole
entity reference: L-Malic acid

Reference/CAS 142185-30-6
type: UnificationXref
id: 142185-30-6
db: CAS

Reference/PubChem-compound 1549095
type: UnificationXref
id: 1549095
db: PubChem-compound

Reference/HMDB HMDB0060153
type: UnificationXref
id: HMDB0060153
db: HMDB

ChemicalStructure/PW C041674
type: ChemicalStructure
structure format: SMILES

2.3.1.133
type: BiochemicalReaction
participant stoichiometry: Compound/PW C096924 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001769 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C041674 Cytosol/Stoichiometry/1.0
right: Coenzyme A
right: 4-Coumaroylshikimic acid
spontaneous: false
EC number: 2.3.1.133
left: Coumaroyl-CoA
left: Shikimic acid
name: Coumaroyl-CoA + Shikimic acid → 4-Coumaroylshikimic acid + Coenzyme A
conversion direction: LEFT_TO_RIGHT

Reference/ChemSpider 937
type: UnificationXref
id: 937
db: ChemSpider

2.3.1.133
type: BiochemicalReaction
participant stoichiometry: Compound/PW C096922 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C044502 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001795 Cytosol/Stoichiometry/1.0
right: Coenzyme A
right: Chlorogenic acid
spontaneous: false
EC number: 2.3.1.133
left: Quinate
left: Caffeoyl-CoA
name: Caffeoyl-CoA + Quinate ← Chlorogenic acid + Coenzyme A
conversion direction: RIGHT_TO_LEFT

Cinnamoyl-CoA
type: SmallMolecule
cellular location: Cytosol
entity reference: Cinnamoyl-CoA
name: SubPathwayOutput

Reference/KEGG Compound C15805
type: UnificationXref
id: C15805
db: KEGG Compound

Reference/KEGG Compound C15804
type: UnificationXref
id: C15804
db: KEGG Compound

Aldehyde dehydrogenase family 2 member C4
type: Protein
cellular location: Cytosol
entity reference: Aldehyde dehydrogenase family 2 member C4

Compound/PW C001065/Stoichiometry/1.0
type: Stoichiometry
physical entity: Oxygen
stoichiometric coefficient: 1.0

Reference/KEGG Compound C15807
type: UnificationXref
id: C15807
db: KEGG Compound

Reference/KEGG Compound C15806
type: UnificationXref
id: C15806
db: KEGG Compound

Compound/PW C001795 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Chlorogenic acid
stoichiometric coefficient: 1.0

Reference/PubChem-compound 637542
type: UnificationXref
id: 637542
db: PubChem-compound

Reference/HMDB HMDB0000097
type: UnificationXref
id: HMDB0000097
db: HMDB

Reference/HMDB HMDB0002035
type: UnificationXref
id: HMDB0002035
db: HMDB

Reference/HMDB HMDB0001185
type: UnificationXref
id: HMDB0001185
db: HMDB

Compound/PW C040034/Stoichiometry/1.0
type: Stoichiometry
physical entity: Hydrogen Ion
stoichiometric coefficient: 1.0

Sinapine
type: SmallMolecule
cellular location: Extracellular Space
entity reference: Sinapine

NADPH
type: SmallMolecule
cellular location: Membrane
entity reference: NADPH

Reference/BioCyc ATP
type: UnificationXref
id: ATP
db: BioCyc

Reference/KEGG Compound C00323
type: UnificationXref
id: C00323
db: KEGG Compound

Serine carboxypeptidase-like 19
type: Protein
cellular location: Extracellular Space
entity reference: Serine carboxypeptidase-like 19

Reference/ChEBI CHEBI 64476
type: UnificationXref
id: CHEBI:64476
db: ChEBI

Reference/ChEBI CHEBI 64475
type: UnificationXref
id: CHEBI:64475
db: ChEBI

Reference/ChEBI CHEBI 64474
type: UnificationXref
id: CHEBI:64474
db: ChEBI

S-Adenosylmethionine
type: SmallMoleculeReference
xref: Reference/PubChem-compound 24762165
xref: Reference/KEGG Compound C00019
xref: Reference/ChemSpider 31983
xref: Reference/ChEBI CHEBI 15414
xref: Reference/CAS 485-80-3
xref: Reference/BioCyc S-ADENOSYLMETHIONINE
xref: Reference/HMDB HMDB0001185
chemical formula: C15H23N6O5S
molecular weight: 399.14505
structure: ChemicalStructure/PW C000921

Reference/ChEBI CHEBI 16119
type: UnificationXref
id: CHEBI:16119
db: ChEBI

Reference/BioCyc 5-HYDROXY-CONIFERYL-ALCOHOL
type: UnificationXref
id: 5-HYDROXY-CONIFERYL-ALCOHOL
db: BioCyc

Compound/PW C000921 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: S-Adenosylmethionine
stoichiometric coefficient: 1.0

ChemicalStructure/PW C016451
type: ChemicalStructure
structure format: SMILES
structure data: COC1=CC(\C=C\C(O)=O)=CC(O)=C1O

Cytochrome P450 98A8
type: Protein
cellular location: Membrane
entity reference: Cytochrome P450 98A8

Compound/PW C108886 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Diphosphoric acid
stoichiometric coefficient: 1.0

Reference/ChEBI CHEBI 16112
type: UnificationXref
id: CHEBI:16112
db: ChEBI

Reference/ChEBI CHEBI 16353
type: UnificationXref
id: CHEBI:16353
db: ChEBI

Reference/ChemSpider 952
type: UnificationXref
id: 952
db: ChemSpider

Reference/CAS 2280-44-6
type: UnificationXref
id: 2280-44-6
db: CAS

Caffeoyl-CoA
type: SmallMolecule
cellular location: Cytosol
entity reference: Caffeoyl-CoA

Reference/ChemSpider 5858
type: UnificationXref
id: 5858
db: ChemSpider

Compound/PW C108955 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: N1,N5-Di(hydroxyferuloyl)-N10-sinapoyl spermidine
stoichiometric coefficient: 1.0

Reference/CAS 537-98-4
type: UnificationXref
id: 537-98-4
db: CAS

Reference/PubChem-compound 6031
type: UnificationXref
id: 6031
db: PubChem-compound

Reference/CAS 133-89-1
type: UnificationXref
id: 133-89-1
db: CAS

Compound/PW C108911 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Caffeyl alcohol
stoichiometric coefficient: 1.0

p-Coumaroyl quinic acid
type: SmallMolecule
cellular location: Cytosol
entity reference: p-Coumaroyl quinic acid

N1,N5,N10-Tricaffeoyl spermidine
type: SmallMolecule
cellular location: Membrane
entity reference: N1,N5,N10-Tricaffeoyl spermidine

Reference/ChemSpider 1010
type: UnificationXref
id: 1010
db: ChemSpider

Compound/PW C104780 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: p-Coumaroyl quinic acid
stoichiometric coefficient: 1.0

Reference/KEGG Compound C00590
type: UnificationXref
id: C00590
db: KEGG Compound

Reference/BioCyc PPI
type: UnificationXref
id: PPI
db: BioCyc

Uridine 5'-diphosphate
type: SmallMolecule
cellular location: Cytosol
entity reference: Uridine 5'-diphosphate

Compound/PW C108951 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: N1,N5,N10-Tricoumaroyl spermidine
stoichiometric coefficient: 1.0

Compound/PW C000414 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Adenosine triphosphate
stoichiometric coefficient: 1.0

Compound/PW C000146 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: NADPH
stoichiometric coefficient: 1.0

trans-Cinnamic acid
type: SmallMoleculeReference
xref: Reference/CAS 621-82-9
xref: Reference/PubChem-compound 444539
xref: Reference/HMDB HMDB0000930
xref: Reference/ChemSpider 392447
xref: Reference/BioCyc CPD-674
xref: Reference/ChEBI CHEBI 35697
xref: Reference/KEGG Compound C00423
chemical formula: C9H8O2
molecular weight: 148.05243
structure: ChemicalStructure/PW C000742

Reaction180137
type: BiochemicalReaction
participant stoichiometry: Compound/Generic302 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C041674 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/Generic303 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C096925 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Membrane/Stoichiometry/1.0
right: [Oxidized NADPH---hemoprotein reductase]
right: Coumaroyl-CoA
right: Water
spontaneous: false
left: Oxygen
left: Cinnamoyl-CoA
left: [Reduced NADPH---hemoprotein reductase]
name: Cinnamoyl-CoA + Oxygen + [Reduced NADPH---hemoprotein reductase] → Coumaroyl-CoA + Water + [Oxidized NADPH---hemoprotein reductase]
conversion direction: LEFT_TO_RIGHT

3,4-Dihydroxy-trans-cinnamate
type: SmallMolecule
cellular location: Cytosol
entity reference: 3,4-Dihydroxy-trans-cinnamate

ChemicalStructure/PW C000921
type: ChemicalStructure
structure format: SMILES

Compound/PW C108920 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Coniferyl aldehyde
stoichiometric coefficient: 1.0

Cytosol
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0005829

Compound/PW C000170 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Pyrophosphate
stoichiometric coefficient: 1.0

Reference/KEGG Compound C00114
type: UnificationXref
id: C00114
db: KEGG Compound

S-Adenosylhomocysteine
type: SmallMoleculeReference
xref: Reference/PubChem-compound 25246222
xref: Reference/ChemSpider 388301
xref: Reference/BioCyc ADENOSYL-HOMO-CYS
xref: Reference/CAS 979-92-0
xref: Reference/KEGG Compound C00021
xref: Reference/ChEBI CHEBI 16680
xref: Reference/HMDB HMDB0000939
chemical formula: C14H20N6O5S
molecular weight: 384.12158
structure: ChemicalStructure/PW C000749

Reference/HMDB HMDB0003164
type: UnificationXref
id: HMDB0003164
db: HMDB

Compound/PW C040034 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Hydrogen Ion
stoichiometric coefficient: 1.0

Reference/ChEBI CHEBI 18361
type: UnificationXref
id: CHEBI:18361
db: ChEBI

Compound/PW C016451 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: 3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid
stoichiometric coefficient: 1.0

Reference/PubChem-compound 637511
type: UnificationXref
id: 637511
db: PubChem-compound

Cinnamate 4-hydroxylase
type: ProteinReference
xref: Reference/UniProt P92994
organism: Arabidopsis thaliana

trans-Ferulic acid
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 17620
xref: Reference/PubChem-compound 445858
xref: Reference/CAS 537-98-4
xref: Reference/HMDB HMDB0000954
xref: Reference/ChemSpider 393368
xref: Reference/KEGG Compound C01494
chemical formula: C10H10O4
molecular weight: 194.0579
structure: ChemicalStructure/PW C000761

phenylalanine ammonia lyase 1
type: ProteinReference
xref: Reference/UniProt P35510
organism: Arabidopsis thaliana

Quinate
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00296
xref: Reference/CAS 17230-85-2
xref: Reference/PubChem-compound 28414
xref: Reference/ChEBI CHEBI 29751
chemical formula: C7H12O6
molecular weight: 192.06339
structure: ChemicalStructure/PW C044502

5-Hydroxy-guaiacyl lignin
type: SmallMolecule
cellular location: Extracellular Space
entity reference: 5-Hydroxy-guaiacyl lignin

5-Hydroxyferuloyl-CoA
type: SmallMolecule
cellular location: Cytosol
entity reference: 5-Hydroxyferuloyl-CoA

Reference/BioCyc COUMARATE
type: UnificationXref
id: COUMARATE
db: BioCyc

Reference/PubChem-compound 446834
type: UnificationXref
id: 446834
db: PubChem-compound

Extracellular Space
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0005615

Reference/BioCyc NAD(P)
type: UnificationXref
id: NAD(P)
db: BioCyc

4-Coumaryl alcohol
type: SmallMolecule
cellular location: Cytosol
entity reference: 4-Coumaryl alcohol

Quercetin 3'-O-methyltransferase
type: ProteinReference
xref: Reference/UniProt Q9FK25
organism: Arabidopsis thaliana

Water
type: SmallMolecule
cellular location: Membrane
entity reference: Water

6.2.1.12
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000414 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001366 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000032 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000170 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C041674 Cytosol/Stoichiometry/1.0
right: Adenosine monophosphate
right: Coumaroyl-CoA
right: Pyrophosphate
spontaneous: false
EC number: 6.2.1.12
left: Adenosine triphosphate
left: 4-Hydroxycinnamic acid
left: Coenzyme A
name: 4-Hydroxycinnamic acid + Adenosine triphosphate + Coenzyme A → Adenosine monophosphate + Coumaroyl-CoA + Pyrophosphate
conversion direction: LEFT_TO_RIGHT

Reference/ChemSpider 388301
type: UnificationXref
id: 388301
db: ChemSpider

Reference/KEGG Compound C00149
type: UnificationXref
id: C00149
db: KEGG Compound

Reference/KEGG Compound C02325
type: UnificationXref
id: C02325
db: KEGG Compound

Guaiacyl lignin
type: SmallMolecule
cellular location: Extracellular Space
entity reference: Guaiacyl lignin

Reference/PubChem-compound 637775
type: UnificationXref
id: 637775
db: PubChem-compound

Compound/PW C000143/Stoichiometry/1.0
type: Stoichiometry
physical entity: NADP
stoichiometric coefficient: 1.0

4-Hydroxycinnamyl alcohol 4-D-glucoside
type: SmallMolecule
cellular location: Nucleus
entity reference: 4-Hydroxycinnamyl alcohol 4-D-glucoside

Reaction212896
type: BiochemicalReaction
participant stoichiometry: Compound/PW C108947 Nucleus/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001949 Nucleus/Stoichiometry/1.0
right: p-Hydroxyphenyl lignin
spontaneous: false
left: 4-Coumaryl alcohol
name: 4-Coumaryl alcohol → p-Hydroxyphenyl lignin
conversion direction: LEFT_TO_RIGHT

Sinapoyl malate
type: SmallMolecule
cellular location: Plant-Type Vacuole
entity reference: Sinapoyl malate

Reaction212897
type: BiochemicalReaction
participant stoichiometry: Compound/PW C008119 Extracellular Space/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108948 Extracellular Space/Stoichiometry/1.0
right: Guaiacyl lignin
spontaneous: false
left: Coniferyl alcohol
name: Coniferyl alcohol → Guaiacyl lignin
conversion direction: LEFT_TO_RIGHT

Reaction212898
type: BiochemicalReaction
participant stoichiometry: Compound/PW C108923 Extracellular Space/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108949 Extracellular Space/Stoichiometry/1.0
right: 5-Hydroxy-guaiacyl lignin
spontaneous: false
left: 5-Hydroxyconiferyl alcohol
name: 5-Hydroxyconiferyl alcohol → 5-Hydroxy-guaiacyl lignin
conversion direction: LEFT_TO_RIGHT

Reaction212899
type: BiochemicalReaction
participant stoichiometry: Compound/PW C108950 Extracellular Space/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008194 Extracellular Space/Stoichiometry/1.0
right: Syringyl lignin
spontaneous: false
left: Sinapyl alcohol
name: Sinapyl alcohol → Syringyl lignin
conversion direction: LEFT_TO_RIGHT

Reference/KEGG Compound C05608
type: UnificationXref
id: C05608
db: KEGG Compound

Compound/PW C108923 Extracellular Space/Stoichiometry/1.0
type: Stoichiometry
physical entity: 5-Hydroxyconiferyl alcohol
stoichiometric coefficient: 1.0

ReactionCatalysis202472
type: Catalysis
controller: Quercetin 3'-O-methyltransferase
controlled: 2.1.1.42
control type: ACTIVATION

ReactionCatalysis202473
type: Catalysis
controller: Cinnamoyl-CoA reductase 1
controlled: Reaction212840
control type: ACTIVATION

Reference/ChEBI CHEBI 31134
type: UnificationXref
id: CHEBI:31134
db: ChEBI

Reference/CAS 328-50-7
type: UnificationXref
id: 328-50-7
db: CAS

Reference/HMDB HMDB0000254
type: UnificationXref
id: HMDB0000254
db: HMDB

Reference/BioCyc AMP
type: UnificationXref
id: AMP
db: BioCyc

ReactionCatalysis202470
type: Catalysis
controller: Caffeoylshikimate esterase
controlled: 3.1.1.-
control type: ACTIVATION

ReactionCatalysis202471
type: Catalysis
controller: 4-coumarate--CoA ligase 1
controlled: Reaction212838
control type: ACTIVATION

Compound/PW C001366 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: 4-Hydroxycinnamic acid
stoichiometric coefficient: 1.0

2.3.1.133
type: BiochemicalReaction
participant stoichiometry: Compound/PW C044502 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C041674 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C104780 Cytosol/Stoichiometry/1.0
right: Coenzyme A
right: p-Coumaroyl quinic acid
spontaneous: false
EC number: 2.3.1.133
left: Coumaroyl-CoA
left: Quinate
name: Coumaroyl-CoA + Quinate → Coenzyme A + p-Coumaroyl quinic acid
conversion direction: LEFT_TO_RIGHT

N1,N5,N10-Tri(hydroxyferuloyl) spermidine
type: SmallMolecule
cellular location: Cytosol
entity reference: N1,N5,N10-Tri(hydroxyferuloyl) spermidine

Reference/HMDB HMDB0000250
type: UnificationXref
id: HMDB0000250
db: HMDB

Sinapic acid
type: SmallMolecule
cellular location: Cytosol
entity reference: Sinapic acid

1.14.14.96
type: BiochemicalReaction
participant stoichiometry: Compound/Generic302 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C104780 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/Generic303 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001795 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Membrane/Stoichiometry/1.0
right: Chlorogenic acid
right: [Oxidized NADPH---hemoprotein reductase]
right: Water
spontaneous: false
EC number: 1.14.14.96
left: Oxygen
left: p-Coumaroyl quinic acid
left: [Reduced NADPH---hemoprotein reductase]
name: Oxygen + [Reduced NADPH---hemoprotein reductase] + p-Coumaroyl quinic acid → Chlorogenic acid + Water + [Oxidized NADPH---hemoprotein reductase]
conversion direction: LEFT_TO_RIGHT

Compound/PW C001890/Stoichiometry/1.0
type: Stoichiometry
physical entity: Cinnamaldehyde
stoichiometric coefficient: 1.0

Compound/PW C108953/Stoichiometry/1.0
type: Stoichiometry
physical entity: N1,N5,N10-Triferuloyl spermidine
stoichiometric coefficient: 1.0

Compound/PW C096923/Stoichiometry/1.0
type: Stoichiometry
physical entity: Feruloyl-CoA
stoichiometric coefficient: 1.0

Reference/KEGG Compound C05619
type: UnificationXref
id: C05619
db: KEGG Compound

Reaction180169
type: BiochemicalReaction
participant stoichiometry: Compound/PW C096922 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C096923 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000749 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000921 Cytosol/Stoichiometry/1.0
right: S-Adenosylhomocysteine
right: Feruloyl-CoA
spontaneous: false
left: Caffeoyl-CoA
left: S-Adenosylmethionine
name: Caffeoyl-CoA + S-Adenosylmethionine → Feruloyl-CoA + S-Adenosylhomocysteine
conversion direction: LEFT_TO_RIGHT

ReactionCatalysis202487
type: Catalysis
controller: Cytochrome P450 84A1
controlled: 1.14.-.-
control type: ACTIVATION

Transport10798
type: Transport
participant stoichiometry: Compound/PW C008119 Extracellular Space/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008119 Cytosol/Stoichiometry/1.0
right: Coniferyl alcohol
spontaneous: false
left: Coniferyl alcohol
name: Coniferyl alcohol (→) Transport: Arabidopsis thaliana, Cell, Cytosol to Arabidopsis thaliana, Cell, Extracellular Space
conversion direction: LEFT_TO_RIGHT

Reference/KEGG Compound C05855
type: UnificationXref
id: C05855
db: KEGG Compound

ReactionCatalysis202488
type: Catalysis
controller: 4-coumarate--CoA ligase 1
controlled: Reaction212856
control type: ACTIVATION

Reference/ChEBI CHEBI 86071
type: UnificationXref
id: CHEBI:86071
db: ChEBI

ReactionCatalysis202489
type: Catalysis
controller: Cinnamoyl-CoA reductase 1
controlled: Reaction212857
control type: ACTIVATION

Reference/KEGG Compound C01494
type: UnificationXref
id: C01494
db: KEGG Compound

Compound/PW C096925 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Cinnamoyl-CoA
stoichiometric coefficient: 1.0

ReactionCatalysis202483
type: Catalysis
controller: Quercetin 3'-O-methyltransferase
controlled: Reaction212851
control type: ACTIVATION

ReactionCatalysis202484
type: Catalysis
controller: Cinnamyl alcohol dehydrogenase
controlled: Reaction212852
control type: ACTIVATION

ReactionCatalysis202485
type: Catalysis
controller: Quercetin 3'-O-methyltransferase
controlled: Reaction212853
control type: ACTIVATION

ReactionCatalysis202486
type: Catalysis
controller: Aldehyde dehydrogenase family 2 member C4
controlled: 1.2.1.3
control type: ACTIVATION

Reference/KEGG Compound C05610
type: UnificationXref
id: C05610
db: KEGG Compound

Transport10797
type: Transport
participant stoichiometry: Compound/PW C001949 Extracellular Space/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001949 Cytosol/Stoichiometry/1.0
right: 4-Coumaryl alcohol
spontaneous: false
left: 4-Coumaryl alcohol
name: 4-Coumaryl alcohol (→) Transport: Arabidopsis thaliana, Cell, Cytosol to Arabidopsis thaliana, Cell, Extracellular Space
conversion direction: LEFT_TO_RIGHT

ReactionCatalysis202480
type: Catalysis
controller: Cinnamyl alcohol dehydrogenase
controlled: Reaction212847
control type: ACTIVATION

ChemicalStructure/PW C000065
type: ChemicalStructure
structure format: SMILES
structure data: C[N+](C)(C)CCO

Cinnamaldehyde
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 16731
xref: Reference/KEGG Compound C00903
xref: Reference/BioCyc CINNAMALDEHYDE
xref: Reference/CAS 14371-10-9
xref: Reference/PubChem-compound 637511
xref: Reference/ChemSpider 553117
xref: Reference/HMDB HMDB0003441
chemical formula: C9H8O
molecular weight: 132.05751
structure: ChemicalStructure/PW C001890

ReactionCatalysis202481
type: Catalysis
controller: 4-coumarate--CoA ligase 1
controlled: Reaction212849
control type: ACTIVATION

ReactionCatalysis202482
type: Catalysis
controller: Cinnamoyl-CoA reductase 1
controlled: Reaction212850
control type: ACTIVATION

Phenylalanine Biosynthesis
type: Pathway
pathway order: SubPathwayInteractionSteps/SubPathway112788
pathway component: SubPathwayInteraction112788
name: SubPathway

Reference/CAS 14371-10-9
type: UnificationXref
id: 14371-10-9
db: CAS

Cinnamaldehyde
type: SmallMolecule
entity reference: Cinnamaldehyde

Ubiquinone Biosynthesis
type: Pathway
pathway order: SubPathwayInteractionSteps/SubPathway112789
pathway component: SubPathwayInteraction112789
name: SubPathway

Reference/CAS 7732-18-5
type: UnificationXref
id: 7732-18-5
db: CAS

Reference/CAS 61-19-8
type: UnificationXref
id: 61-19-8
db: CAS

ChemicalStructure/PW C000032
type: ChemicalStructure
structure format: SMILES

ChemicalStructure/PW C001366
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)\C=C\C1=CC=C(O)C=C1

ChemicalStructure/PW C108886
type: ChemicalStructure
structure format: SMILES
structure data: OP(O)(=O)OP(O)(O)=O

Stillbenoid Diarylhe Ptanoid and Gingerol Biosynthesis
type: Pathway
pathway order: SubPathwayInteractionSteps/SubPathway112791
pathway component: SubPathwayInteraction112791
name: SubPathway

Reference/ChEBI CHEBI 61514
type: UnificationXref
id: CHEBI:61514
db: ChEBI

Flavonoid Biosynthesis
type: Pathway
pathway order: SubPathwayInteractionSteps/SubPathway112790
pathway component: SubPathwayInteraction112790
name: SubPathway

p-Coumaraldehyde
type: SmallMoleculeReference
xref: Reference/PubChem-compound 641301
xref: Reference/KEGG Compound C05608
xref: Reference/ChEBI CHEBI \28353
chemical formula: C9H8O2
molecular weight: 148.05243
structure: ChemicalStructure/PW C108903

Reference/UniProt Q42524
type: UnificationXref
id: Q42524
db: UniProt

Compound/PW C000143 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: NADP
stoichiometric coefficient: 1.0

ReactionCatalysis202469
type: Catalysis
controller: Hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase
controlled: Reaction212836
control type: ACTIVATION

5-O-Caffeoylshikimic acid
type: SmallMoleculeReference
xref: Reference/KEGG Compound C10434
xref: Reference/ChEBI CHEBI 2106
xref: Reference/PubChem-compound 25243950
chemical formula: C16H16O8
molecular weight: 336.0845
structure: ChemicalStructure/PW C108909

Reference/BioCyc SINAPYL-ALCOHOL
type: UnificationXref
id: SINAPYL-ALCOHOL
db: BioCyc

Reference/ChEBI CHEBI 17295
type: UnificationXref
id: CHEBI:17295
db: ChEBI

trans-Cinnamic acid
type: SmallMolecule
cellular location: Membrane
entity reference: trans-Cinnamic acid

ReactionCatalysis202466
type: Catalysis
controller: Cinnamoyl-CoA reductase 1
controlled: Reaction212828
control type: ACTIVATION

ReactionCatalysis202467
type: Catalysis
controller: Cinnamyl alcohol dehydrogenase
controlled: 1.1.1.195
control type: ACTIVATION

ReactionCatalysis202468
type: Catalysis
controller: Cytochrome P450 98A3
controlled: Reaction212835
control type: ACTIVATION

ReactionCatalysis202463
type: Catalysis
controller: 4-coumarate--CoA ligase 1
controlled: Reaction212823
control type: ACTIVATION

ReactionCatalysis202464
type: Catalysis
controller: Cinnamoyl-CoA reductase 1
controlled: Reaction212824
control type: ACTIVATION

Reference/HMDB HMDB0001377
type: UnificationXref
id: HMDB0001377
db: HMDB

Oxygen
type: SmallMolecule
cellular location: Membrane
entity reference: Oxygen

Cinnamate 4-hydroxylase
type: Protein
cellular location: Membrane
entity reference: Cinnamate 4-hydroxylase

Reference/HMDB HMDB0000045
type: UnificationXref
id: HMDB0000045
db: HMDB

S-Adenosylhomocysteine
type: SmallMolecule
cellular location: Cytosol
entity reference: S-Adenosylhomocysteine

Reference/PubChem-compound 329728082
type: UnificationXref
id: 329728082
db: PubChem-compound

Reference/BioCyc PHE
type: UnificationXref
id: PHE
db: BioCyc

Caffeic aldehyde
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 28323
xref: Reference/KEGG Compound C10945
xref: Reference/PubChem-compound 5281871
chemical formula: C9H8O3
molecular weight: 164.04735
structure: ChemicalStructure/PW C108910

Reference/UniProt Q9FI78
type: UnificationXref
id: Q9FI78
db: UniProt

Caffeyl alcohol
type: SmallMoleculeReference
xref: Reference/KEGG Compound C12206
xref: Reference/PubChem-compound 14352
xref: Reference/ChEBI CHEBI 86071
chemical formula: C9H10O3
molecular weight: 166.06299
structure: ChemicalStructure/PW C108911

Compound/PW C108910 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Caffeic aldehyde
stoichiometric coefficient: 1.0

Reference/HMDB HMDB0000286
type: UnificationXref
id: HMDB0000286
db: HMDB

Reaction212851
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000749 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000921 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108920 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108910 Cytosol/Stoichiometry/1.0
right: S-Adenosylhomocysteine
right: Coniferyl aldehyde
spontaneous: false
left: Caffeic aldehyde
left: S-Adenosylmethionine
name: Caffeic aldehyde + S-Adenosylmethionine → Coniferyl aldehyde + S-Adenosylhomocysteine
conversion direction: LEFT_TO_RIGHT

Reaction212852
type: BiochemicalReaction
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108920 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008119 Cytosol/Stoichiometry/1.0
right: Hydrogen Ion
right: Coniferyl aldehyde
right: NADPH
spontaneous: false
left: Coniferyl alcohol
left: NADP
name: Coniferyl alcohol + NADP ← Coniferyl aldehyde + Hydrogen Ion + NADPH
conversion direction: RIGHT_TO_LEFT

Reaction212853
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000749 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000921 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108911 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008119 Cytosol/Stoichiometry/1.0
right: S-Adenosylhomocysteine
right: Coniferyl alcohol
spontaneous: false
left: Caffeyl alcohol
left: S-Adenosylmethionine
name: Caffeyl alcohol + S-Adenosylmethionine → Coniferyl alcohol + S-Adenosylhomocysteine
conversion direction: LEFT_TO_RIGHT

Compound/PW C108952 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: N1,N5,N10-Tricaffeoyl spermidine
stoichiometric coefficient: 1.0

1.2.1.3
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000761 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108920 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Cytosol/Stoichiometry/1.0
right: Hydrogen Ion
right: trans-Ferulic acid
right: NADPH
spontaneous: false
EC number: 1.2.1.3
left: Coniferyl aldehyde
left: NADP
left: Water
name: Coniferyl aldehyde + NADP + Water → Hydrogen Ion + NADPH + trans-Ferulic acid
conversion direction: LEFT_TO_RIGHT

1.14.-.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000143 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C016451 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000761 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Membrane/Stoichiometry/1.0
right: 3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid
right: NADP
right: Water
spontaneous: false
EC number: 1.14.-.-
left: Oxygen
left: Hydrogen Ion
left: NADPH
left: trans-Ferulic acid
name: Hydrogen Ion + NADPH + Oxygen + trans-Ferulic acid → 3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid + NADP + Water
conversion direction: LEFT_TO_RIGHT

Reaction212856
type: BiochemicalReaction
participant stoichiometry: Compound/PW C016451 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000414 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108921 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000032 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108886 Cytosol/Stoichiometry/1.0
right: Adenosine monophosphate
right: 5-Hydroxyferuloyl-CoA
right: Diphosphoric acid
spontaneous: false
left: Adenosine triphosphate
left: Coenzyme A
left: 3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid
name: 3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid + Adenosine triphosphate + Coenzyme A → 5-Hydroxyferuloyl-CoA + Adenosine monophosphate + Diphosphoric acid
conversion direction: LEFT_TO_RIGHT

L-Phenylalanine
type: SmallMoleculeReference
xref: Reference/PubChem-compound 6140
xref: Reference/HMDB HMDB0000159
xref: Reference/ChemSpider 5910
xref: Reference/ChEBI CHEBI 17295
xref: Reference/BioCyc PHE
xref: Reference/CAS 63-91-2
xref: Reference/KEGG Compound C00079
chemical formula: C9H11NO2
molecular weight: 165.07898
structure: ChemicalStructure/PW C000104

Reaction212857
type: BiochemicalReaction
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108922 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108921 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Cytosol/Stoichiometry/1.0
right: Coenzyme A
right: 5-Hydroxyconiferaldehyde
right: NADP
spontaneous: false
left: Hydrogen Ion
left: 5-Hydroxyferuloyl-CoA
left: NADPH
name: 5-Hydroxyferuloyl-CoA + Hydrogen Ion + NADPH → 5-Hydroxyconiferaldehyde + Coenzyme A + NADP
conversion direction: LEFT_TO_RIGHT

Reaction212858
type: BiochemicalReaction
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108923 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108922 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Cytosol/Stoichiometry/1.0
right: 5-Hydroxyconiferyl alcohol
right: NADP
spontaneous: false
left: Hydrogen Ion
left: 5-Hydroxyconiferaldehyde
left: NADPH
name: 5-Hydroxyconiferaldehyde + Hydrogen Ion + NADPH ? 5-Hydroxyconiferyl alcohol + NADP

Reference/KEGG Compound C01533
type: UnificationXref
id: C01533
db: KEGG Compound

Reference/UniProt Q9S9N9
type: UnificationXref
id: Q9S9N9
db: UniProt

Reference/ChemSpider 21864784
type: UnificationXref
id: 21864784
db: ChemSpider

Sinapyl alcohol
type: SmallMolecule
cellular location: Extracellular Space
entity reference: Sinapyl alcohol

Reference/ChemSpider 21864782
type: UnificationXref
id: 21864782
db: ChemSpider

Reaction212850
type: BiochemicalReaction
participant stoichiometry: Compound/PW C096923 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108920 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Cytosol/Stoichiometry/1.0
right: Feruloyl-CoA
right: Hydrogen Ion
right: NADPH
spontaneous: false
left: Coenzyme A
left: Coniferyl aldehyde
left: NADP
name: Coenzyme A + Coniferyl aldehyde + NADP ← Feruloyl-CoA + Hydrogen Ion + NADPH
conversion direction: RIGHT_TO_LEFT

UDP-glycosyltransferase 84A2
type: Protein
cellular location: Cytosol
entity reference: UDP-glycosyltransferase 84A2

Oxoglutaric acid
type: SmallMolecule
entity reference: Oxoglutaric acid

Reaction212859
type: BiochemicalReaction
participant stoichiometry: Compound/PW C096923 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108921 Cytosol/Stoichiometry/1.0
right: 5-Hydroxyferuloyl-CoA
spontaneous: false
left: Feruloyl-CoA
name: Feruloyl-CoA → 5-Hydroxyferuloyl-CoA
conversion direction: LEFT_TO_RIGHT

Coniferyl aldehyde
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 16547
xref: Reference/PubChem-compound 5637
xref: Reference/KEGG Compound C02666
chemical formula: C10H10O3
molecular weight: 178.06299
structure: ChemicalStructure/PW C108920

5-Hydroxyferuloyl-CoA
type: SmallMoleculeReference
xref: Reference/PubChem-compound 14349
xref: Reference/ChEBI CHEBI 31136
xref: Reference/KEGG Compound C12203
chemical formula: C31H44N7O20P3S
molecular weight: 959.1575
structure: ChemicalStructure/PW C108921

5-Hydroxyconiferaldehyde
type: SmallMoleculeReference
xref: Reference/PubChem-compound 14350
xref: Reference/KEGG Compound C12204
xref: Reference/ChEBI CHEBI 31134
chemical formula: C10H10O4
molecular weight: 194.0579
structure: ChemicalStructure/PW C108922

Reference/HMDB HMDB0000295
type: UnificationXref
id: HMDB0000295
db: HMDB

5-Hydroxyconiferyl alcohol
type: SmallMoleculeReference
xref: Reference/KEGG Compound C12205
xref: Reference/ChEBI CHEBI 86068
xref: Reference/PubChem-compound 14351
chemical formula: C10H12O4
molecular weight: 196.07356
structure: ChemicalStructure/PW C108923

Reference/ChemSpider 5809
type: UnificationXref
id: 5809
db: ChemSpider

Reaction212862
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000143 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008119 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108923 Membrane/Stoichiometry/1.0
right: 5-Hydroxyconiferyl alcohol
right: NADP
right: Water
spontaneous: false
left: Oxygen
left: Hydrogen Ion
left: NADPH
left: Coniferyl alcohol
name: Coniferyl alcohol + Hydrogen Ion + NADPH + Oxygen → 5-Hydroxyconiferyl alcohol + NADP + Water
conversion direction: LEFT_TO_RIGHT

Compound/PW C108956 Nucleus/Stoichiometry/1.0
type: Stoichiometry
physical entity: Syringin
stoichiometric coefficient: 1.0

ReactionCatalysis37595
type: Catalysis
controller: phenylalanine ammonia lyase 1
controlled: 4.3.1.24
control type: ACTIVATION

Reaction212863
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000749 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C016451 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000921 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C013713 Cytosol/Stoichiometry/1.0
right: S-Adenosylhomocysteine
right: Sinapic acid
spontaneous: false
left: 3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid
left: S-Adenosylmethionine
name: 3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid + S-Adenosylmethionine → S-Adenosylhomocysteine + Sinapic acid
conversion direction: LEFT_TO_RIGHT

Reaction212864
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000414 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C013713 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108928 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000032 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108886 Cytosol/Stoichiometry/1.0
right: Adenosine monophosphate
right: Sinapoyl-CoA
right: Diphosphoric acid
spontaneous: false
left: Adenosine triphosphate
left: Coenzyme A
left: Sinapic acid
name: Adenosine triphosphate + Coenzyme A + Sinapic acid → Adenosine monophosphate + Diphosphoric acid + Sinapoyl-CoA
conversion direction: LEFT_TO_RIGHT

Sinapoyl-CoA
type: SmallMoleculeReference
xref: Reference/PubChem-compound 3701
xref: Reference/KEGG Compound C00411
xref: Reference/ChEBI CHEBI 15540
chemical formula: C32H46N7O20P3S
molecular weight: 973.1731
structure: ChemicalStructure/PW C108928

2.1.1.104
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000749 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000921 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108928 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108921 Cytosol/Stoichiometry/1.0
right: S-Adenosylhomocysteine
right: Sinapoyl-CoA
spontaneous: false
EC number: 2.1.1.104
left: 5-Hydroxyferuloyl-CoA
left: S-Adenosylmethionine
name: 5-Hydroxyferuloyl-CoA + S-Adenosylmethionine → S-Adenosylhomocysteine + Sinapoyl-CoA
conversion direction: LEFT_TO_RIGHT

Sinapoyl aldehyde
type: SmallMoleculeReference
xref: Reference/PubChem-compound 7932
xref: Reference/ChEBI CHEBI 27949
xref: Reference/KEGG Compound C05610
chemical formula: C11H12O4
molecular weight: 208.07356
structure: ChemicalStructure/PW C108929

Reaction212866
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108928 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108929 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Cytosol/Stoichiometry/1.0
right: Sinapoyl-CoA
right: Hydrogen Ion
right: NADPH
spontaneous: false
left: Coenzyme A
left: NADP
left: Sinapoyl aldehyde
name: Coenzyme A + NADP + Sinapoyl aldehyde ← Hydrogen Ion + NADPH + Sinapoyl-CoA
conversion direction: RIGHT_TO_LEFT

Compound/PW C000104 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: L-Phenylalanine
stoichiometric coefficient: 1.0

Reference/UniProt O22203
type: UnificationXref
id: O22203
db: UniProt

3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid
type: SmallMolecule
cellular location: Cytosol
entity reference: 3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid

Reaction212867
type: BiochemicalReaction
participant stoichiometry: Compound/PW C008194 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108929 Cytosol/Stoichiometry/1.0
right: Hydrogen Ion
right: Sinapoyl aldehyde
right: NADPH
spontaneous: false
left: Sinapyl alcohol
left: NADP
name: NADP + Sinapyl alcohol ← Hydrogen Ion + NADPH + Sinapoyl aldehyde
conversion direction: RIGHT_TO_LEFT

Reaction212868
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000749 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000921 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108922 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108929 Cytosol/Stoichiometry/1.0
right: S-Adenosylhomocysteine
right: Sinapoyl aldehyde
spontaneous: false
left: 5-Hydroxyconiferaldehyde
left: S-Adenosylmethionine
name: 5-Hydroxyconiferaldehyde + S-Adenosylmethionine → S-Adenosylhomocysteine + Sinapoyl aldehyde
conversion direction: LEFT_TO_RIGHT

Reaction212869
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000749 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008194 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108923 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000921 Cytosol/Stoichiometry/1.0
right: S-Adenosylhomocysteine
right: Sinapyl alcohol
spontaneous: false
left: 5-Hydroxyconiferyl alcohol
left: S-Adenosylmethionine
name: 5-Hydroxyconiferyl alcohol + S-Adenosylmethionine → S-Adenosylhomocysteine + Sinapyl alcohol
conversion direction: LEFT_TO_RIGHT

ReactionCatalysis169991
type: Catalysis
controller: Cinnamate 4-hydroxylase
controlled: Reaction180137
control type: ACTIVATION

4-coumarate--CoA ligase 1
type: Protein
cellular location: Cytosol
entity reference: 4-coumarate--CoA ligase 1

Reaction212861
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000143 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108920 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108922 Membrane/Stoichiometry/1.0
right: 5-Hydroxyconiferaldehyde
right: NADP
right: Water
spontaneous: false
left: Oxygen
left: Coniferyl aldehyde
left: Hydrogen Ion
left: NADPH
name: Coniferyl aldehyde + Hydrogen Ion + NADPH + Oxygen → 5-Hydroxyconiferaldehyde + NADP + Water
conversion direction: LEFT_TO_RIGHT

6-Hydroxyferuloyl-CoA
type: SmallMoleculeReference
xref: Reference/PubChem-compound 329728082
xref: Reference/KEGG Compound C21459
chemical formula: C31H44N7O20P3S
molecular weight: 959.1575
structure: ChemicalStructure/PW C108931

6-Hydroxyferuloyl-CoA
type: SmallMolecule
entity reference: 6-Hydroxyferuloyl-CoA

Compound/PW C108957 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: 1-O-Sinapoyl-beta-D-glucose
stoichiometric coefficient: 1.0

Reference/ChEBI CHEBI 86068
type: UnificationXref
id: CHEBI:86068
db: ChEBI

Compound/Generic303 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: [Oxidized NADPH---hemoprotein reductase]
stoichiometric coefficient: 1.0

Reference/PubChem-compound 6083
type: UnificationXref
id: 6083
db: PubChem-compound

ReactionCatalysis202498
type: Catalysis
controller: Caffeoyl-CoA O-methyltransferase 1
controlled: 2.1.1.104
control type: ACTIVATION

ReactionCatalysis202499
type: Catalysis
controller: Cinnamoyl-CoA reductase 1
controlled: Reaction212866
control type: ACTIVATION

3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid
type: SmallMolecule
cellular location: Membrane
entity reference: 3-(3,4-Dihydroxy-5-methoxy)-2-propenoic acid

Compound/PW C108958 Plant-Type Vacuole/Stoichiometry/1.0
type: Stoichiometry
physical entity: Sinapoyl malate
stoichiometric coefficient: 1.0

ReactionCatalysis202494
type: Catalysis
controller: Cytochrome P450 84A1
controlled: Reaction212861
control type: ACTIVATION

ReactionCatalysis202495
type: Catalysis
controller: Cytochrome P450 84A1
controlled: Reaction212862
control type: ACTIVATION

Reaction212870
type: BiochemicalReaction
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000146 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C013713 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108929 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000143 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Cytosol/Stoichiometry/1.0
right: Hydrogen Ion
right: Sinapic acid
right: NADPH
spontaneous: false
left: NADP
left: Sinapoyl aldehyde
left: Water
name: NADP + Sinapoyl aldehyde + Water → Hydrogen Ion + NADPH + Sinapic acid
conversion direction: LEFT_TO_RIGHT

ReactionCatalysis202496
type: Catalysis
controller: Quercetin 3'-O-methyltransferase
controlled: Reaction212863
control type: ACTIVATION

1.14.11.61
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001316/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065/Stoichiometry/1.0
participant stoichiometry: Compound/PW C096923/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108931/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000174/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000134/Stoichiometry/1.0
right: Succinic acid
right: Carbon dioxide
right: 6-Hydroxyferuloyl-CoA
spontaneous: false
EC number: 1.14.11.61
left: Oxoglutaric acid
left: Feruloyl-CoA
left: Oxygen
name: Feruloyl-CoA + Oxoglutaric acid + Oxygen → 6-Hydroxyferuloyl-CoA + Carbon dioxide + Succinic acid
conversion direction: LEFT_TO_RIGHT

ReactionCatalysis202497
type: Catalysis
controller: 4-coumarate--CoA ligase 1
controlled: Reaction212864
control type: ACTIVATION

ReactionCatalysis202490
type: Catalysis
controller: Cinnamyl alcohol dehydrogenase
controlled: Reaction212858
control type: ACTIVATION

ChemicalStructure/PW C000077
type: ChemicalStructure
structure format: SMILES

Reference/PubChem-compound 22833512
type: UnificationXref
id: 22833512
db: PubChem-compound

Compound/Generic302 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: [Reduced NADPH---hemoprotein reductase]
stoichiometric coefficient: 1.0

Reference/PubChem-compound 25246222
type: UnificationXref
id: 25246222
db: PubChem-compound

Water
type: SmallMoleculeReference
xref: Reference/PubChem-compound 962
xref: Reference/ChEBI CHEBI 15377
xref: Reference/KEGG Compound C00001
xref: Reference/ChemSpider 937
xref: Reference/HMDB HMDB0002111
xref: Reference/CAS 7732-18-5
chemical formula: H2O
molecular weight: 18.010565
structure: ChemicalStructure/PW C001420

Ammonium
type: SmallMolecule
cellular location: Cytosol
entity reference: Ammonium

N1,N5-Di(hydroxyferuloyl)-N10-sinapoyl spermidine
type: SmallMolecule
cellular location: Cytosol
entity reference: N1,N5-Di(hydroxyferuloyl)-N10-sinapoyl spermidine

p-Hydroxyphenyl lignin
type: SmallMoleculeReference
xref: Reference/KEGG Compound C15804
xref: Reference/ChEBI CHEBI 64474
xref: Reference/PubChem-compound 47205129

Guaiacyl lignin
type: SmallMoleculeReference
xref: Reference/KEGG Compound C15805
xref: Reference/ChEBI CHEBI 64475
xref: Reference/PubChem-compound 47205130

5-Hydroxy-guaiacyl lignin
type: SmallMoleculeReference
xref: Reference/PubChem-compound 47205132
xref: Reference/KEGG Compound C15807
xref: Reference/ChEBI CHEBI 80099

4-Hydroxycinnamic acid
type: SmallMolecule
cellular location: Cytosol
entity reference: 4-Hydroxycinnamic acid

Reference/HMDB HMDB0041827
type: UnificationXref
id: HMDB0041827
db: HMDB

Reference/HMDB HMDB0059597
type: UnificationXref
id: HMDB0059597
db: HMDB

Compound/PW C000065 Extracellular Space/Stoichiometry/1.0
type: Stoichiometry
physical entity: Choline
stoichiometric coefficient: 1.0

Compound/PW C022608 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Ammonium
stoichiometric coefficient: 1.0

Reference/ChEBI CHEBI 31136
type: UnificationXref
id: CHEBI:31136
db: ChEBI

Syringyl lignin
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 64476
xref: Reference/PubChem-compound 47205131
xref: Reference/KEGG Compound C15806

N1,N5,N10-Tricoumaroyl spermidine
type: SmallMoleculeReference
xref: Reference/PubChem-compound 96024287
xref: Reference/KEGG Compound C18069
xref: Reference/ChEBI CHEBI 61514
chemical formula: C34H37N3O6
molecular weight: 583.26825
structure: ChemicalStructure/PW C108951

N1,N5,N10-Tricaffeoyl spermidine
type: SmallMoleculeReference
xref: Reference/KEGG Compound C18070
xref: Reference/ChEBI CHEBI 81478
xref: Reference/PubChem-compound 96024288
chemical formula: C34H37N3O9
molecular weight: 631.253
structure: ChemicalStructure/PW C108952

L-Malic acid
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0000156
xref: Reference/ChEBI CHEBI 30797
xref: Reference/KEGG Compound C00149
xref: Reference/ChemSpider 193317
xref: Reference/PubChem-compound 222656
xref: Reference/CAS 97-67-6
chemical formula: C4H6O5
molecular weight: 134.02153
structure: ChemicalStructure/PW C000101

N1,N5,N10-Triferuloyl spermidine
type: SmallMoleculeReference
xref: Reference/KEGG Compound C18071
xref: Reference/PubChem-compound 96024289
xref: Reference/ChEBI CHEBI 81479
chemical formula: C37H43N3O9
molecular weight: 673.2999
structure: ChemicalStructure/PW C108953

N1,N5,N10-Tri(hydroxyferuloyl) spermidine
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 81480
xref: Reference/PubChem-compound 96024290
xref: Reference/KEGG Compound C18072
chemical formula: C37H43N3O12
molecular weight: 721.28467
structure: ChemicalStructure/PW C108954

N1,N5-Di(hydroxyferuloyl)-N10-sinapoyl spermidine
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00019
xref: Reference/PubChem-compound 96024291
xref: Reference/ChEBI CHEBI 61516
chemical formula: C38H45N3O12
molecular weight: 735.30035
structure: ChemicalStructure/PW C108955

Syringin
type: SmallMoleculeReference
xref: Reference/KEGG Compound C01533
xref: Reference/PubChem-compound 4695
xref: Reference/ChEBI CHEBI 9380
chemical formula: C17H24O9
molecular weight: 372.14203
structure: ChemicalStructure/PW C108956

Serine carboxypeptidase-like 8
type: Protein
cellular location: Plant-Type Vacuole
entity reference: Serine carboxypeptidase-like 8

N1,N5,N10-Tricaffeoyl spermidine
type: SmallMolecule
entity reference: N1,N5,N10-Tricaffeoyl spermidine

1-O-Sinapoyl-beta-D-glucose
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 16546
xref: Reference/PubChem-compound 4402
xref: Reference/KEGG Compound C01175
chemical formula: C17H22O10
molecular weight: 386.1213
structure: ChemicalStructure/PW C108957

N1,N5,N10-Triferuloyl spermidine
type: SmallMolecule
entity reference: N1,N5,N10-Triferuloyl spermidine

Sinapoyl malate
type: SmallMoleculeReference
xref: Reference/PubChem-compound 5818
xref: Reference/KEGG Compound C02887
xref: Reference/ChEBI CHEBI 139533
chemical formula: C15H16O9
molecular weight: 340.07944
structure: ChemicalStructure/PW C108958

Reference/BioCyc CINNAMALDEHYDE
type: UnificationXref
id: CINNAMALDEHYDE
db: BioCyc

Reference/ChEBI CHEBI 35697
type: UnificationXref
id: CHEBI:35697
db: ChEBI

Reference/KEGG Compound C03024
type: UnificationXref
id: C03024
db: KEGG Compound

Compound/PW C108949 Extracellular Space/Stoichiometry/1.0
type: Stoichiometry
physical entity: 5-Hydroxy-guaiacyl lignin
stoichiometric coefficient: 1.0

Succinic acid
type: SmallMolecule
entity reference: Succinic acid

Compound/PW C000749 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: S-Adenosylhomocysteine
stoichiometric coefficient: 1.0

ChemicalStructure/PW C001420
type: ChemicalStructure
structure format: SMILES
structure data: O

Reference/CAS 621-82-9
type: UnificationXref
id: 621-82-9
db: CAS

Compound/PW C104813 Nucleus/Stoichiometry/1.0
type: Stoichiometry
physical entity: 4-Hydroxycinnamyl alcohol 4-D-glucoside
stoichiometric coefficient: 1.0

Compound/PW C000742 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: trans-Cinnamic acid
stoichiometric coefficient: 1.0

Compound/PW C000143 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: NADP
stoichiometric coefficient: 1.0

Compound/PW C096924 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: 4-Coumaroylshikimic acid
stoichiometric coefficient: 1.0

ChemicalStructure/PW C000101
type: ChemicalStructure
structure format: SMILES
structure data: O[C@@H](CC(O)=O)C(O)=O

Cinnamoyl-CoA reductase 1
type: Protein
entity reference: Cinnamoyl-CoA reductase 1

N1,N5,N10-Tri(hydroxyferuloyl) spermidine
type: SmallMolecule
cellular location: Membrane
entity reference: N1,N5,N10-Tri(hydroxyferuloyl) spermidine

Compound/PW C108947 Nucleus/Stoichiometry/1.0
type: Stoichiometry
physical entity: p-Hydroxyphenyl lignin
stoichiometric coefficient: 1.0

Reference/CAS 53-59-8
type: UnificationXref
id: 53-59-8
db: CAS

Reference/PubChem-compound 1038
type: UnificationXref
id: 1038
db: PubChem-compound

1-O-Sinapoyl-beta-D-glucose
type: SmallMolecule
cellular location: Plant-Type Vacuole
entity reference: 1-O-Sinapoyl-beta-D-glucose

Reference/GENE ONTOLOGY GO 0005829
type: UnificationXref
id: GO:0005829
db: GENE ONTOLOGY

Compound/PW C000201 Nucleus/Stoichiometry/1.0
type: Stoichiometry
physical entity: Uridine 5'-diphosphate
stoichiometric coefficient: 1.0

Reference/PubChem-compound 5637
type: UnificationXref
id: 5637
db: PubChem-compound

Reference/ChEBI CHEBI 61516
type: UnificationXref
id: CHEBI:61516
db: ChEBI

Reference/UniProt Q9FK25
type: UnificationXref
id: Q9FK25
db: UniProt

Oxoglutaric acid
type: SmallMoleculeReference
xref: Reference/CAS 328-50-7
xref: Reference/PubChem-compound 51
xref: Reference/BioCyc 2-KETOGLUTARATE
xref: Reference/HMDB HMDB0000208
xref: Reference/ChEBI CHEBI 30915
xref: Reference/KEGG Compound C00026
xref: Reference/ChemSpider 50
chemical formula: C5H6O5
molecular weight: 146.02153
structure: ChemicalStructure/PW C000134

Shikimic acid
type: SmallMolecule
cellular location: Cytosol
entity reference: Shikimic acid

4-Coumaroylshikimic acid
type: SmallMolecule
cellular location: Membrane
entity reference: 4-Coumaroylshikimic acid

Reference/BioCyc ADENOSYL-HOMO-CYS
type: UnificationXref
id: ADENOSYL-HOMO-CYS
db: BioCyc

Reference/PubChem-compound 5280372
type: UnificationXref
id: 5280372
db: PubChem-compound

NADPH
type: SmallMolecule
entity reference: NADPH

Reference/PubChem-compound 1023
type: UnificationXref
id: 1023
db: PubChem-compound

ChemicalStructure/PW C001890
type: ChemicalStructure
structure format: SMILES
structure data: O=C\C=C\C1=CC=CC=C1

Reference/UniProt P48523
type: UnificationXref
id: P48523
db: UniProt

NADP
type: SmallMolecule
entity reference: NADP

Reference/CAS 331-39-5
type: UnificationXref
id: 331-39-5
db: CAS

NADPH
type: SmallMoleculeReference
xref: Reference/CAS 53-57-6
xref: Reference/HMDB HMDB0000221
xref: Reference/PubChem-compound 22833512
xref: Reference/BioCyc NADPH
xref: Reference/ChemSpider 17215925
xref: Reference/KEGG Compound C00005
xref: Reference/ChEBI CHEBI 16474
chemical formula: C21H30N7O17P3
molecular weight: 745.0911
structure: ChemicalStructure/PW C000146

Chlorogenic acid
type: SmallMolecule
cellular location: Cytosol
entity reference: Chlorogenic acid

NADP
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00006
xref: Reference/CAS 53-59-8
xref: Reference/BioCyc NAD(P)
xref: Reference/HMDB HMDB0000217
xref: Reference/ChEBI CHEBI 18009
xref: Reference/PubChem-compound 5886
xref: Reference/ChemSpider 5675
chemical formula: C21H28N7O17P3
molecular weight: 743.07544
structure: ChemicalStructure/PW C000143

Reference/ChemSpider 600426
type: UnificationXref
id: 600426
db: ChemSpider

Reference/ChEBI CHEBI 16731
type: UnificationXref
id: CHEBI:16731
db: ChEBI

Reference/HMDB HMDB0000208
type: UnificationXref
id: HMDB0000208
db: HMDB

trans-Ferulic acid
type: SmallMolecule
cellular location: Membrane
entity reference: trans-Ferulic acid

Uridine diphosphate glucose
type: SmallMoleculeReference
xref: Reference/BioCyc UDP-GLUCOSE
xref: Reference/KEGG Compound C00029
xref: Reference/PubChem-compound 53477679
xref: Reference/CAS 133-89-1
xref: Reference/HMDB HMDB0000286
chemical formula: C15H24N2O17P2
molecular weight: 566.055
structure: ChemicalStructure/PW C000193

Coniferin
type: SmallMolecule
cellular location: Nucleus
entity reference: Coniferin

Reference/PubChem-compound 5818
type: UnificationXref
id: 5818
db: PubChem-compound

Reference/HMDB HMDB0000217
type: UnificationXref
id: HMDB0000217
db: HMDB

ChemicalStructure/PW C000134
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)CCC(=O)C(O)=O

Oxygen
type: SmallMolecule
entity reference: Oxygen

Diphosphoric acid
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 29888
xref: Reference/CAS 2466-09-3
xref: Reference/KEGG Compound C00013
xref: Reference/PubChem-compound 1023
chemical formula: H4O7P2
molecular weight: 177.94322
structure: ChemicalStructure/PW C108886

Reference/CAS 124-38-9
type: UnificationXref
id: 124-38-9
db: CAS

Compound/PW C096923 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Feruloyl-CoA
stoichiometric coefficient: 1.0

Reference/ChemSpider 4444067
type: UnificationXref
id: 4444067
db: ChemSpider

Reference/ChEBI CHEBI 15414
type: UnificationXref
id: CHEBI:15414
db: ChEBI

Reaction212900
type: BiochemicalReaction
participant stoichiometry: Compound/PW C108951 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C041674 Cytosol/Stoichiometry/1.0
right: N1,N5,N10-Tricoumaroyl spermidine
spontaneous: false
left: Coumaroyl-CoA
name: Coumaroyl-CoA → N1,N5,N10-Tricoumaroyl spermidine
conversion direction: LEFT_TO_RIGHT

1.14.-.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C108952 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108951 Membrane/Stoichiometry/1.0
right: N1,N5,N10-Tricaffeoyl spermidine
spontaneous: false
EC number: 1.14.-.-
left: N1,N5,N10-Tricoumaroyl spermidine
name: N1,N5,N10-Tricoumaroyl spermidine → N1,N5,N10-Tricaffeoyl spermidine
conversion direction: LEFT_TO_RIGHT

5.4.99.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C108953/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108952/Stoichiometry/1.0
right: N1,N5,N10-Triferuloyl spermidine
spontaneous: false
EC number: 5.4.99.-
left: N1,N5,N10-Tricaffeoyl spermidine
name: N1,N5,N10-Tricaffeoyl spermidine → N1,N5,N10-Triferuloyl spermidine
conversion direction: LEFT_TO_RIGHT

p-Coumaroyl quinic acid
type: SmallMoleculeReference
xref: Reference/KEGG Compound C12208
xref: Reference/ChEBI CHEBI 15937
chemical formula: C16H18O8
molecular weight: 338.10016
structure: ChemicalStructure/PW C104780

Reference/KEGG Compound C02666
type: UnificationXref
id: C02666
db: KEGG Compound

Reference/BioCyc GLC
type: UnificationXref
id: GLC
db: BioCyc

Compound/PW C108922 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: 5-Hydroxyconiferaldehyde
stoichiometric coefficient: 1.0

ChemicalStructure/PW C000143
type: ChemicalStructure
structure format: SMILES

Reference/HMDB HMDB0000221
type: UnificationXref
id: HMDB0000221
db: HMDB

Reference/PubChem-compound 5280555
type: UnificationXref
id: 5280555
db: PubChem-compound

ChemicalStructure/PW C000146
type: ChemicalStructure
structure format: SMILES

Reaction212903
type: BiochemicalReaction
participant stoichiometry: Compound/PW C108953 Membrane/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108954 Membrane/Stoichiometry/1.0
right: N1,N5,N10-Tri(hydroxyferuloyl) spermidine
spontaneous: false
left: N1,N5,N10-Triferuloyl spermidine
name: N1,N5,N10-Triferuloyl spermidine → N1,N5,N10-Tri(hydroxyferuloyl) spermidine
conversion direction: LEFT_TO_RIGHT

Reference/GENE ONTOLOGY GO 0005634
type: UnificationXref
id: GO:0005634
db: GENE ONTOLOGY

2.1.1.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000749 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108955 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108954 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000921 Cytosol/Stoichiometry/1.0
right: S-Adenosylhomocysteine
right: N1,N5-Di(hydroxyferuloyl)-N10-sinapoyl spermidine
spontaneous: false
EC number: 2.1.1.-
left: N1,N5,N10-Tri(hydroxyferuloyl) spermidine
left: S-Adenosylmethionine
name: N1,N5,N10-Tri(hydroxyferuloyl) spermidine + S-Adenosylmethionine → N1,N5-Di(hydroxyferuloyl)-N10-sinapoyl spermidine + S-Adenosylhomocysteine
conversion direction: LEFT_TO_RIGHT

2.4.1.111,2.4.1.126
type: BiochemicalReaction
participant stoichiometry: Compound/PW C104813 Nucleus/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000201 Nucleus/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001949 Nucleus/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000193 Nucleus/Stoichiometry/1.0
right: Uridine 5'-diphosphate
right: 4-Hydroxycinnamyl alcohol 4-D-glucoside
spontaneous: false
EC number: 2.4.1.111,2.4.1.126
left: Uridine diphosphate glucose
left: 4-Coumaryl alcohol
name: 4-Coumaryl alcohol + Uridine diphosphate glucose → 4-Hydroxycinnamyl alcohol 4-D-glucoside + Uridine 5'-diphosphate
conversion direction: LEFT_TO_RIGHT

Reaction212906
type: BiochemicalReaction
participant stoichiometry: Compound/PW C008119 Nucleus/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000201 Nucleus/Stoichiometry/1.0
participant stoichiometry: Compound/PW C008558 Nucleus/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000193 Nucleus/Stoichiometry/1.0
right: Coniferin
right: Uridine 5'-diphosphate
spontaneous: false
left: Uridine diphosphate glucose
left: Coniferyl alcohol
name: Coniferyl alcohol + Uridine diphosphate glucose → Coniferin + Uridine 5'-diphosphate
conversion direction: LEFT_TO_RIGHT

Reaction212907
type: BiochemicalReaction
participant stoichiometry: Compound/PW C008194 Nucleus/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108956 Nucleus/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000201 Nucleus/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000193 Nucleus/Stoichiometry/1.0
right: Uridine 5'-diphosphate
right: Syringin
spontaneous: false
left: Sinapyl alcohol
left: Uridine diphosphate glucose
name: Sinapyl alcohol + Uridine diphosphate glucose → Syringin + Uridine 5'-diphosphate
conversion direction: LEFT_TO_RIGHT

2.4.1.120
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000193 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C013713 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000201 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108957 Cytosol/Stoichiometry/1.0
right: 1-O-Sinapoyl-beta-D-glucose
right: Uridine 5'-diphosphate
spontaneous: false
EC number: 2.4.1.120
left: Uridine diphosphate glucose
left: Sinapic acid
name: Sinapic acid + Uridine diphosphate glucose → 1-O-Sinapoyl-beta-D-glucose + Uridine 5'-diphosphate
conversion direction: LEFT_TO_RIGHT

Reference/CAS 53-57-6
type: UnificationXref
id: 53-57-6
db: CAS

Reference/KEGG Compound C00811
type: UnificationXref
id: C00811
db: KEGG Compound

Compound/PW C040034 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Hydrogen Ion
stoichiometric coefficient: 1.0

2.3.1.92,2.3.1.103
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000101 Plant-Type Vacuole/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108957 Plant-Type Vacuole/Stoichiometry/1.0
participant stoichiometry: Compound/PW C108958 Plant-Type Vacuole/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000077 Plant-Type Vacuole/Stoichiometry/1.0
right: Sinapoyl malate
right: D-Glucose
spontaneous: false
EC number: 2.3.1.92,2.3.1.103
left: L-Malic acid
left: 1-O-Sinapoyl-beta-D-glucose
name: 1-O-Sinapoyl-beta-D-glucose + L-Malic acid → D-Glucose + Sinapoyl malate
conversion direction: LEFT_TO_RIGHT

2.3.1.91
type: BiochemicalReaction
participant stoichiometry: Compound/PW C108957 Extracellular Space/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000065 Extracellular Space/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000077 Extracellular Space/Stoichiometry/1.0
participant stoichiometry: Compound/PW C010625 Extracellular Space/Stoichiometry/1.0
right: Choline
right: 1-O-Sinapoyl-beta-D-glucose
spontaneous: false
EC number: 2.3.1.91
left: Sinapine
left: D-Glucose
name: D-Glucose + Sinapine ← 1-O-Sinapoyl-beta-D-glucose + Choline
conversion direction: RIGHT_TO_LEFT

Reference/BioCyc S-ADENOSYLMETHIONINE
type: UnificationXref
id: S-ADENOSYLMETHIONINE
db: BioCyc

Reference/ChEBI CHEBI 28938
type: UnificationXref
id: CHEBI:28938
db: ChEBI

ChemicalStructure/PW C000104
type: ChemicalStructure
structure format: SMILES
structure data: N[C@@H](CC1=CC=CC=C1)C(O)=O

Caffeoyl-CoA O-methyltransferase 1
type: Protein
cellular location: Cytosol
entity reference: Caffeoyl-CoA O-methyltransferase 1

Reference/KEGG Compound C21459
type: UnificationXref
id: C21459
db: KEGG Compound

Reference/HMDB HMDB0003501
type: UnificationXref
id: HMDB0003501
db: HMDB

Compound/PW C041674 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Coumaroyl-CoA
stoichiometric coefficient: 1.0

Pyrophosphate
type: SmallMoleculeReference
xref: Reference/PubChem-compound 644102
xref: Reference/BioCyc PPI
xref: Reference/ChemSpider 559142
xref: Reference/ChEBI CHEBI 18361
xref: Reference/HMDB HMDB0000250
xref: Reference/CAS 14000-31-8
xref: Reference/KEGG Compound C00013
chemical formula: H4O7P2
molecular weight: 177.94322
structure: ChemicalStructure/PW C000170

Coniferyl alcohol
type: SmallMolecule
cellular location: Cytosol
entity reference: Coniferyl alcohol

trans-Ferulic acid
type: SmallMolecule
cellular location: Cytosol
entity reference: trans-Ferulic acid

Succinic acid
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0000254
xref: Reference/CAS 110-15-6
xref: Reference/ChEBI CHEBI 15741
xref: Reference/KEGG Compound C00042
xref: Reference/ChemSpider 1078
xref: Reference/PubChem-compound 1110
xref: Reference/BioCyc SUC
chemical formula: C4H6O4
molecular weight: 118.02661
structure: ChemicalStructure/PW C000174

Caffeoylshikimate esterase
type: Protein
cellular location: Membrane
entity reference: Caffeoylshikimate esterase

Chlorogenic acid
type: SmallMolecule
cellular location: Membrane
entity reference: Chlorogenic acid

Reference/BioCyc CPD-563
type: UnificationXref
id: CPD-563
db: BioCyc

Compound/PW C108923 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: 5-Hydroxyconiferyl alcohol
stoichiometric coefficient: 1.0

Quercetin 3'-O-methyltransferase
type: Protein
cellular location: Cytosol
entity reference: Quercetin 3'-O-methyltransferase

SubPathwayInteraction112790
type: Interaction
name: SubPathwayReaction
name: SubPathway112790Reaction
participant: Coumaroyl-CoA
participant: Cinnamoyl-CoA

Reference/UniProt Q9C942
type: UnificationXref
id: Q9C942
db: UniProt

SubPathwayInteraction112791
type: Interaction
name: SubPathwayReaction
name: SubPathway112791Reaction
participant: Coumaroyl-CoA
participant: Cinnamoyl-CoA

Adenosine triphosphate
type: SmallMolecule
cellular location: Cytosol
entity reference: Adenosine triphosphate

Reference/CAS 138-59-0
type: UnificationXref
id: 138-59-0
db: CAS

Reference/GENE ONTOLOGY GO 0005615
type: UnificationXref
id: GO:0005615
db: GENE ONTOLOGY

Cinnamyl alcohol dehydrogenase 4
type: Protein
cellular location: Cytosol
entity reference: Cinnamyl alcohol dehydrogenase 4

SubPathwayInteraction112788
type: Interaction
name: SubPathway112788Reaction
name: SubPathwayReaction
participant: L-Phenylalanine

Hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase
type: Protein
cellular location: Cytosol
entity reference: Hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase

SubPathwayInteraction112789
type: Interaction
name: SubPathwayReaction
name: SubPathway112789Reaction
participant: trans-Cinnamic acid

Compound/PW C096924 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: 4-Coumaroylshikimic acid
stoichiometric coefficient: 1.0

3,4-Dihydroxy-trans-cinnamate
type: SmallMolecule
cellular location: Membrane
entity reference: 3,4-Dihydroxy-trans-cinnamate

Uridine diphosphate glucose
type: SmallMolecule
cellular location: Nucleus
entity reference: Uridine diphosphate glucose

Compound/PW C041674 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Coumaroyl-CoA
stoichiometric coefficient: 1.0

Sinapoyl aldehyde
type: SmallMolecule
cellular location: Cytosol
entity reference: Sinapoyl aldehyde

Reference/BioCyc CAFFEOYLQUINATE
type: UnificationXref
id: CAFFEOYLQUINATE
db: BioCyc

ChemicalStructure/PW C104813
type: ChemicalStructure
structure format: SMILES

Reference/ChEBI CHEBI 17620
type: UnificationXref
id: CHEBI:17620
db: ChEBI

5-Hydroxyconiferaldehyde
type: SmallMolecule
cellular location: Cytosol
entity reference: 5-Hydroxyconiferaldehyde

N1,N5,N10-Triferuloyl spermidine
type: SmallMolecule
cellular location: Membrane
entity reference: N1,N5,N10-Triferuloyl spermidine

Reference/ChEBI CHEBI 1146900
type: UnificationXref
id: CHEBI:1146900
db: ChEBI

Reference/ChEBI CHEBI 80099
type: UnificationXref
id: CHEBI:80099
db: ChEBI

Cytochrome P450 98A3
type: Protein
cellular location: Membrane
entity reference: Cytochrome P450 98A3

Reference/ChEBI CHEBI 16547
type: UnificationXref
id: CHEBI:16547
db: ChEBI

Reference/ChEBI CHEBI 16546
type: UnificationXref
id: CHEBI:16546
db: ChEBI

Reference/UniProt Q8RUW5
type: UnificationXref
id: Q8RUW5
db: UniProt

S-Adenosylmethionine
type: SmallMolecule
cellular location: Cytosol
entity reference: S-Adenosylmethionine

Coenzyme A
type: SmallMolecule
entity reference: Coenzyme A

ABC transporter G family member 29
type: Protein
entity reference: ABC transporter G family member 29

Coenzyme A
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 1146900
xref: Reference/HMDB HMDB0001423
xref: Reference/PubChem-compound 6816
xref: Reference/BioCyc CO-A
xref: Reference/ChemSpider 6557
xref: Reference/CAS 85-61-0
xref: Reference/KEGG Compound C00010
chemical formula: C21H36N7O16P3S
molecular weight: 767.11523
structure: ChemicalStructure/PW C001099

Reference/ChEBI CHEBI 2106
type: UnificationXref
id: CHEBI:2106
db: ChEBI

Compound/PW C000032 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Adenosine monophosphate
stoichiometric coefficient: 1.0

Reference/CAS 2041-35-2
type: UnificationXref
id: 2041-35-2
db: CAS

Reference/ChemSpider 80576
type: UnificationXref
id: 80576
db: ChemSpider

Reference/ChEBI CHEBI 15422
type: UnificationXref
id: CHEBI:15422
db: ChEBI

Reference/ChemSpider 5589
type: UnificationXref
id: 5589
db: ChemSpider

Compound/PW C108957 Extracellular Space/Stoichiometry/1.0
type: Stoichiometry
physical entity: 1-O-Sinapoyl-beta-D-glucose
stoichiometric coefficient: 1.0

Compound/PW C108903 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: p-Coumaraldehyde
stoichiometric coefficient: 1.0

Compound/PW C001949 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: 4-Coumaryl alcohol
stoichiometric coefficient: 1.0

Arabidopsis thaliana
type: BioSource
xref: Reference/TAXONOMY 3702

Reference/KEGG Compound C00852
type: UnificationXref
id: C00852
db: KEGG Compound

Compound/PW C001065 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Oxygen
stoichiometric coefficient: 1.0

Reference/PubChem-compound 25243950
type: UnificationXref
id: 25243950
db: PubChem-compound

4.3.1.24
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000104 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000742 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C022608 Cytosol/Stoichiometry/1.0
right: Ammonium
right: trans-Cinnamic acid
spontaneous: false
EC number: 4.3.1.24
left: L-Phenylalanine
name: L-Phenylalanine → Ammonium + trans-Cinnamic acid
conversion direction: LEFT_TO_RIGHT

Reference/PubChem-compound 8742
type: UnificationXref
id: 8742
db: PubChem-compound

Oxygen
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0001377
xref: Reference/ChemSpider 952
xref: Reference/KEGG Compound C00007
xref: Reference/ChEBI CHEBI 15379
xref: Reference/PubChem-compound 977
xref: Reference/BioCyc CPD-6641
xref: Reference/CAS 7782-44-7
chemical formula: O2
molecular weight: 31.98983
structure: ChemicalStructure/PW C001065

1-O-Sinapoyl-beta-D-glucose
type: SmallMolecule
cellular location: Cytosol
entity reference: 1-O-Sinapoyl-beta-D-glucose

Reference/PubChem-compound 5281871
type: UnificationXref
id: 5281871
db: PubChem-compound

Reference/CAS 537-33-7
type: UnificationXref
id: 537-33-7
db: CAS

Uridine 5'-diphosphate
type: SmallMolecule
cellular location: Nucleus
entity reference: Uridine 5'-diphosphate

Reference/ChEBI CHEBI 16526
type: UnificationXref
id: CHEBI:16526
db: ChEBI

UDP-glycosyltransferase 72E3
type: Protein
cellular location: Nucleus
entity reference: UDP-glycosyltransferase 72E3

Reference/PubChem-compound 5280535
type: UnificationXref
id: 5280535
db: PubChem-compound

Reference/PubChem-compound 11966126
type: UnificationXref
id: 11966126
db: PubChem-compound

Reference/BioCyc 3-DEHYDRO-SHIKIMATE
type: UnificationXref
id: 3-DEHYDRO-SHIKIMATE
db: BioCyc

Reference/PubChem-compound 11966129
type: UnificationXref
id: 11966129
db: PubChem-compound

Compound/PW C001420 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Water
stoichiometric coefficient: 1.0

Feruloyl CoA ortho-hydroxylase 2
type: Protein
entity reference: Feruloyl CoA ortho-hydroxylase 2

Reference/PubChem-compound 28414
type: UnificationXref
id: 28414
db: PubChem-compound

Compound/PW C001420 Membrane/Stoichiometry/1.0
type: Stoichiometry
physical entity: Water
stoichiometric coefficient: 1.0

ChemicalStructure/PW C044502
type: ChemicalStructure
structure format: SMILES

UDP-glycosyltransferase 72E3
type: ProteinReference
xref: Reference/UniProt O81498
organism: Arabidopsis thaliana

Uridine diphosphate glucose
type: SmallMolecule
cellular location: Cytosol
entity reference: Uridine diphosphate glucose

Cytochrome P450 98A8
type: ProteinReference
xref: Reference/UniProt Q9CA61
organism: Arabidopsis thaliana

Tapetum-specific methyltransferase 1
type: ProteinReference
xref: Reference/UniProt Q9C9W4
organism: Arabidopsis thaliana

ABC transporter G family member 29
type: ProteinReference
xref: Reference/UniProt Q94A18

Reference/ChEBI CHEBI 28323
type: UnificationXref
id: CHEBI:28323
db: ChEBI

Coumaroyl-CoA
type: SmallMolecule
cellular location: Cytosol
entity reference: Coumaroyl-CoA
name: SubPathwayOutput

Compound/PW C108957 Plant-Type Vacuole/Stoichiometry/1.0
type: Stoichiometry
physical entity: 1-O-Sinapoyl-beta-D-glucose
stoichiometric coefficient: 1.0

Reference/CAS 3690-05-9
type: UnificationXref
id: 3690-05-9
db: CAS

Coniferyl alcohol
type: SmallMolecule
cellular location: Nucleus
entity reference: Coniferyl alcohol

Reference/ChEBI CHEBI 15499
type: UnificationXref
id: CHEBI:15499
db: ChEBI

5-Hydroxyconiferyl alcohol
type: SmallMolecule
cellular location: Extracellular Space
entity reference: 5-Hydroxyconiferyl alcohol

phenylalanine ammonia lyase 1
type: Protein
cellular location: Cytosol
entity reference: phenylalanine ammonia lyase 1

Reference/KEGG Compound C00406
type: UnificationXref
id: C00406
db: KEGG Compound

Reference/PubChem-compound 5886
type: UnificationXref
id: 5886
db: PubChem-compound

Serine carboxypeptidase-like 19
type: ProteinReference
xref: Reference/UniProt Q8VZU3
organism: Arabidopsis thaliana

ReactionCatalysis98498
type: Catalysis
controller: Hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase
controlled: 2.3.1.133
control type: ACTIVATION

Reference/ChEBI CHEBI 29888
type: UnificationXref
id: CHEBI:29888
db: ChEBI

Reference/PubChem-compound 280
type: UnificationXref
id: 280
db: PubChem-compound

UDP-glycosyltransferase 84A2
type: ProteinReference
xref: Reference/UniProt Q9LVF0
organism: Arabidopsis thaliana

Serine carboxypeptidase-like 8
type: ProteinReference
xref: Reference/UniProt Q8RUW5
organism: Arabidopsis thaliana

Membrane
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0016020

Reference/PubChem-compound 96024287
type: UnificationXref
id: 96024287
db: PubChem-compound

Reference/PubChem-compound 16741146
type: UnificationXref
id: 16741146
db: PubChem-compound

Reference/CAS 2466-09-3
type: UnificationXref
id: 2466-09-3
db: CAS

ChemicalStructure/PW C000742
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)\C=C\C1=CC=CC=C1

Reference/ChemSpider 8412
type: UnificationXref
id: 8412
db: ChemSpider

ChemicalStructure/PW C000749
type: ChemicalStructure
structure format: SMILES

Reference/PubChem-compound 96024289
type: UnificationXref
id: 96024289
db: PubChem-compound

Reference/ChEBI CHEBI 9380
type: UnificationXref
id: CHEBI:9380
db: ChEBI

Compound/PW C108948 Extracellular Space/Stoichiometry/1.0
type: Stoichiometry
physical entity: Guaiacyl lignin
stoichiometric coefficient: 1.0

Reference/PubChem-compound 96024288
type: UnificationXref
id: 96024288
db: PubChem-compound

Reference/ChEBI CHEBI 15463
type: UnificationXref
id: CHEBI:15463
db: ChEBI

ReactionCatalysis98499
type: Catalysis
controller: Hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase
controlled: 2.3.1.133
control type: ACTIVATION

Reference/CAS 1021913-49-4
type: UnificationXref
id: 1021913-49-4
db: CAS

Reference/ChemSpider 193317
type: UnificationXref
id: 193317
db: ChemSpider

Reference/PubChem-compound 5280507
type: UnificationXref
id: 5280507
db: PubChem-compound

Reference/PubChem-compound 96024290
type: UnificationXref
id: 96024290
db: PubChem-compound

Reference/ChEBI CHEBI 17659
type: UnificationXref
id: CHEBI:17659
db: ChEBI

Reference/PubChem-compound 96024291
type: UnificationXref
id: 96024291
db: PubChem-compound

Reference/HMDB HMDB0001967
type: UnificationXref
id: HMDB0001967
db: HMDB

Reference/KEGG Compound C00423
type: UnificationXref
id: C00423
db: KEGG Compound

Reference/PubChem-compound 24762165
type: UnificationXref
id: 24762165
db: PubChem-compound

ChemicalStructure/PW C000761
type: ChemicalStructure
structure format: SMILES
structure data: COC1=C(O)C=CC(\C=C\C(O)=O)=C1

ReactionCatalysis170150
type: Catalysis
controller: Cinnamate 4-hydroxylase
controlled: Reaction180294
control type: ACTIVATION