trans-4-coumaroyl-CoA
type: SmallMolecule
cellular location: Cytosol
entity reference: trans-4-coumaroyl-CoA

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

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

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

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

Reference/ChEBI CHEBI 58210
type: UnificationXref
id: CHEBI:58210
db: ChEBI

Reference/ChEBI CHEBI 59789
type: UnificationXref
id: CHEBI:59789
db: ChEBI

ferulic acid
type: SmallMoleculeReference
xref: Reference/PubChem-compound 54691413
xref: Reference/ChEBI CHEBI 29749
xref: Reference/CAS 1135-24-6
xref: Reference/ChemSpider 4573888
chemical formula: C10H9O4
molecular weight: 193.05063
structure: ChemicalStructure/PW C057841

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

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

Coumarin Biosynthesis
type: Pathway
pathway order: PathwayEnzymeReaction/9868044
pathway order: PathwayEnzymeReaction/9868043
pathway order: PathwayEnzymeReaction/9868046
pathway order: PathwayEnzymeReaction/9868045
pathway order: PathwayEnzymeReaction/9868037
pathway order: PathwayEnzymeReaction/9868048
pathway order: PathwayTransport/9868035
pathway order: PathwayEnzymeReaction/9868036
pathway order: PathwayEnzymeReaction/9868047
pathway order: PathwayEnzymeReaction/9868039
pathway order: PathwayEnzymeReaction/9868038
pathway order: PathwayEnzymeReaction/9868040
pathway order: PathwayEnzymeReaction/9868042
pathway order: PathwayEnzymeReaction/9868163
pathway order: PathwayEnzymeReaction/9868196
pathway order: PathwayEnzymeReaction/9868041
pathway order: PathwaySubPathway/843806
pathway component: 1.14.14.-
pathway component: Reaction2146826
pathway component: Transport100627
pathway component: 1.14.11.60
pathway component: 2.1.1.42
pathway component: Reaction2146825
pathway component: Reaction2146822
pathway component: 4.3.1.24
pathway component: 1.14.11.61
pathway component: Reaction2146820
pathway component: Reaction2146821
pathway component: Reaction2146860
pathway component: ReactionCatalysis37595
pathway component: ReactionCatalysis2178354
pathway component: ReactionCatalysis2178353
pathway component: ReactionCatalysis2178352
pathway component: ReactionCatalysis2178351
pathway component: ReactionCatalysis2178350
pathway component: ReactionCatalysis2178394
pathway component: 6.2.1.12
pathway component: Reaction2146857
pathway component: Reaction2146771
pathway component: ReactionCatalysis2178307
pathway component: ReactionCatalysis2178349
pathway component: ReactionCatalysis2178348
pathway component: ReactionCatalysis2178347
pathway component: Phenylalanine Metabolism
xref: Reference/PathWhiz PW766993
xref: Reference/SMPDB SMP0729214
organism: Arabidopsis thaliana

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

ChemicalStructure/PW C104784
type: ChemicalStructure
structure format: SMILES

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

Compound/PW C285196 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Esculetin
stoichiometric coefficient: 1.0

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

Compound/PW C285185 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: trans-4-coumaroyl-CoA
stoichiometric coefficient: 1.0

Compound/PW C285178 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: diphosphate(3−)
stoichiometric coefficient: 1.0

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

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

Compound/PW C011089 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Umbelliferone
stoichiometric coefficient: 1.0

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

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

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

ChemicalStructure/PW C015392
type: ChemicalStructure
structure format: SMILES
structure data: COC1=C(O)C=C2OC(=O)C=CC2=C1

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

Scoparone
type: SmallMoleculeReference
xref: Reference/ChemSpider 8110
xref: Reference/KEGG Compound C09311
xref: Reference/CAS 120-08-1
xref: Reference/ChEBI CHEBI 284936
xref: Reference/HMDB HMDB0030818
xref: Reference/PubChem-compound 8417
chemical formula: C11H10O4
molecular weight: 206.0579
structure: ChemicalStructure/PW C012022

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

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

Reference/UniProt Q9LHN8
type: UnificationXref
id: Q9LHN8
db: UniProt

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

Reference/ChEBI CHEBI 33019
type: UnificationXref
id: CHEBI:33019
db: ChEBI

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

Reaction2146771
type: BiochemicalReaction
participant stoichiometry: Compound/PW C104784 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000742 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000891 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285184 Cytosol/Stoichiometry/1.0
right: Hydrogen Ion
right: FMN
right: trans-4-coumarate
right: Water
spontaneous: false
left: Oxygen
left: FMNH2
left: trans-Cinnamic acid
name: FMNH2 + Oxygen + trans-Cinnamic acid → FMN + Hydrogen Ion + Water + trans-4-coumarate
conversion direction: LEFT_TO_RIGHT

trans-caffeoyl-CoA
type: SmallMolecule
cellular location: Cytosol
entity reference: trans-caffeoyl-CoA

Reference/ChEBI CHEBI 490095
type: UnificationXref
id: CHEBI:490095
db: ChEBI

Reference/HMDB HMDB0029865
type: UnificationXref
id: HMDB0029865
db: HMDB

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

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

Reference/UniProt Q9LU36
type: UnificationXref
id: Q9LU36
db: UniProt

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

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

Reference/CAS 120-08-1
type: UnificationXref
id: 120-08-1
db: CAS

Reference/GENE ONTOLOGY GO 0009507
type: UnificationXref
id: GO:0009507
db: GENE ONTOLOGY

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

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

ChemicalStructure/PW C285178
type: ChemicalStructure
structure format: SMILES
structure data: OP([O-])(=O)OP([O-])([O-])=O

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

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

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

Reference/PubChem-compound 445395
type: UnificationXref
id: 445395
db: PubChem-compound

Reference/CAS 93-35-6
type: UnificationXref
id: 93-35-6
db: CAS

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

ChemicalStructure/PW C001099
type: ChemicalStructure
structure format: SMILES

4-coumarate--CoA ligase 2
type: ProteinReference
xref: Reference/UniProt Q9S725
organism: Arabidopsis thaliana

Flavone 3'-O-methyltransferase 1
type: ProteinReference
xref: Reference/UniProt Q9FK25
organism: Arabidopsis thaliana

trans-6-hydroxyferuloyl-CoA
type: SmallMolecule
cellular location: Cytosol
entity reference: trans-6-hydroxyferuloyl-CoA

Feruloyl CoA ortho-hydroxylase 1
type: ProteinReference
xref: Reference/UniProt Q9LHN8
organism: Arabidopsis thaliana

Reference/ChEBI CHEBI 142390
type: UnificationXref
id: CHEBI:142390
db: ChEBI

Scopoletin 8-hydroxylase
type: ProteinReference
xref: Reference/UniProt Q9LE86
organism: Arabidopsis thaliana

Xanthotoxin 5-hydroxylase CYP82C4
type: ProteinReference
xref: Reference/UniProt Q9SZ46
organism: Arabidopsis thaliana

Compound/PW C015392 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Scopoletin
stoichiometric coefficient: 1.0

Reference/CAS 5666-16-0
type: UnificationXref
id: 5666-16-0
db: CAS

ReactionCatalysis2178307
type: Catalysis
controller: Cinnamate 4-hydroxylase
controlled: Reaction2146771
control type: ACTIVATION

Feruloyl CoA ortho-hydroxylase 1
type: Protein
cellular location: Cytosol
entity reference: Feruloyl CoA ortho-hydroxylase 1

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

SubPathwayInteraction843806
type: Interaction
name: SubPathway843806Reaction
name: SubPathwayReaction
participant: L-Phenylalanine

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

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

Carbon dioxide
type: SmallMolecule
cellular location: Cytosol
entity reference: Carbon dioxide

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

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

Umbelliferone
type: SmallMoleculeReference
xref: Reference/PubChem-compound 5281426
xref: Reference/ChEBI CHEBI 27510
xref: Reference/ChemSpider 4444774
xref: Reference/CAS 93-35-6
xref: Reference/HMDB HMDB0029865
xref: Reference/KEGG Compound C09315
chemical formula: C9H6O3
molecular weight: 162.0317
structure: ChemicalStructure/PW C011089

Reference/HMDB HMDB0034344
type: UnificationXref
id: HMDB0034344
db: HMDB

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

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

ChemicalStructure/PW C285193
type: ChemicalStructure
structure format: SMILES

Reference/UniProt Q9S725
type: UnificationXref
id: Q9S725
db: UniProt

ChemicalStructure/PW C285192
type: ChemicalStructure
structure format: SMILES

Reference/ChEBI CHEBI 27510
type: UnificationXref
id: CHEBI:27510
db: ChEBI

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

ChemicalStructure/PW C285191
type: ChemicalStructure
structure format: SMILES
structure data: [H]\C(=C(\[H])C1=CC(O)=C([O-])C=C1)C(O)=O

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

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

Compound/PW C285199 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Sideretin
stoichiometric coefficient: 1.0

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

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

ChemicalStructure/PW C285198
type: ChemicalStructure
structure format: SMILES
structure data: COC1=C(O)C(O)=C2OC(=O)C=CC2=C1

ChemicalStructure/PW C285196
type: ChemicalStructure
structure format: SMILES
structure data: OC1=C(O)C=C2C=CC(=O)OC2=C1

ChemicalStructure/PW C285195
type: ChemicalStructure
structure format: SMILES

ChemicalStructure/PW C285194
type: ChemicalStructure
structure format: SMILES

Reference/PubChem-compound 5281416
type: UnificationXref
id: 5281416
db: PubChem-compound

Flavone 3'-O-methyltransferase 1
type: Protein
cellular location: Cytosol
entity reference: Flavone 3'-O-methyltransferase 1

S-adenosyl-L-methionine zwitterion
type: SmallMolecule
cellular location: Cytosol
entity reference: S-adenosyl-L-methionine zwitterion

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

FMN
type: SmallMoleculeReference
xref: Reference/KEGG Compound C00061
xref: Reference/ChEBI CHEBI 58210
xref: Reference/PubChem-compound 44229199
chemical formula: C17H18N4O9P
molecular weight: 453.0828
structure: ChemicalStructure/PW C104784

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

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

Reaction2146857
type: BiochemicalReaction
participant stoichiometry: Compound/PW C011089 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285196 Cytosol/Stoichiometry/1.0
right: Esculetin
spontaneous: false
left: Oxygen
left: Umbelliferone
name: Oxygen + Umbelliferone → Esculetin
conversion direction: LEFT_TO_RIGHT

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

Reference/ChemSpider 8110
type: UnificationXref
id: 8110
db: ChemSpider

Compound/PW C104784 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: FMN
stoichiometric coefficient: 1.0

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

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

ChemicalStructure/PW C285184
type: ChemicalStructure
structure format: SMILES
structure data: OC1=CC=C(\C=C\C([O-])=O)C=C1

Reference/PubChem-compound 54691413
type: UnificationXref
id: 54691413
db: PubChem-compound

Reference/ChEBI CHEBI 17488
type: UnificationXref
id: CHEBI:17488
db: ChEBI

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

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

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

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

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

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

Reference/PubChem-compound 5280460
type: UnificationXref
id: 5280460
db: PubChem-compound

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

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

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

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

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

Transport100627
type: Transport
participant stoichiometry: Compound/PW C000104 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000104 Chloroplast/Stoichiometry/1.0
right: L-Phenylalanine
spontaneous: false
left: L-Phenylalanine
name: L-Phenylalanine (→) Transport: Arabidopsis thaliana, Cell, Chloroplast to Arabidopsis thaliana, Cell, Cytosol
conversion direction: LEFT_TO_RIGHT

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

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

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

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

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

Reaction2146860
type: BiochemicalReaction
participant stoichiometry: Compound/PW C285191 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000134 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000174 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001316 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285185 Cytosol/Stoichiometry/1.0
right: trans-caffeate
right: Succinic acid
right: Carbon dioxide
spontaneous: false
left: trans-4-coumaroyl-CoA
left: Oxygen
left: Oxoglutaric acid
name: Oxoglutaric acid + Oxygen + trans-4-coumaroyl-CoA → Carbon dioxide + Succinic acid + trans-caffeate
conversion direction: LEFT_TO_RIGHT

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

Reference/ChEBI CHEBI 85008
type: UnificationXref
id: CHEBI:85008
db: ChEBI

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

Reference/ChEBI CHEBI 87305
type: UnificationXref
id: CHEBI:87305
db: ChEBI

Reference/ChEBI CHEBI 16048
type: UnificationXref
id: CHEBI:16048
db: ChEBI

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

ReactionCatalysis2178354
type: Catalysis
controller: Xanthotoxin 5-hydroxylase CYP82C4
controlled: 1.14.14.-
control type: ACTIVATION

ReactionCatalysis2178353
type: Catalysis
controller: Scopoletin 8-hydroxylase
controlled: 1.14.11.60
control type: ACTIVATION

ReactionCatalysis2178352
type: Catalysis
controller: Flavone 3'-O-methyltransferase 1
controlled: 2.1.1.42
control type: ACTIVATION

ReactionCatalysis2178351
type: Catalysis
controller: Feruloyl CoA ortho-hydroxylase 1
controlled: 1.14.11.61
control type: ACTIVATION

ReactionCatalysis2178350
type: Catalysis
controller: 4-coumarate--CoA ligase 4
controlled: Reaction2146821
control type: ACTIVATION

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

Reference/PubChem-compound 8417
type: UnificationXref
id: 8417
db: PubChem-compound

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

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

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

Reference/PubChem-compound 5281426
type: UnificationXref
id: 5281426
db: PubChem-compound

Reference/PathWhiz PW766993
type: UnificationXref
id: PW766993
db: PathWhiz

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

FMNH2
type: SmallMolecule
cellular location: Cytosol
entity reference: FMNH2

Xanthotoxin 5-hydroxylase CYP82C4
type: Protein
cellular location: Cytosol
entity reference: Xanthotoxin 5-hydroxylase CYP82C4

ReactionCatalysis2178349
type: Catalysis
controller: 4-coumarate--CoA ligase 1
controlled: Reaction2146820
control type: ACTIVATION

ReactionCatalysis2178348
type: Catalysis
controller: Flavone 3'-O-methyltransferase 1
controlled: 2.1.1.42
control type: ACTIVATION

ReactionCatalysis2178347
type: Catalysis
controller: 4-coumarate--CoA ligase 2
controlled: 6.2.1.12
control type: ACTIVATION

trans-feruloyl-CoA(4−)
type: SmallMolecule
cellular location: Cytosol
entity reference: trans-feruloyl-CoA(4−)

Phenylalanine Metabolism
type: Pathway
pathway order: SubPathwayInteractionSteps/SubPathway843806
pathway component: SubPathwayInteraction843806
xref: Reference/PathWhiz PW002552
xref: Reference/SMPDB SMP0002442
name: SubPathway

Compound/PW C057841 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: ferulic acid
stoichiometric coefficient: 1.0

Compound/PW C285198 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Fraxetin
stoichiometric coefficient: 1.0

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

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

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

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

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

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

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

Reference/ChEBI CHEBI 5169
type: UnificationXref
id: CHEBI:5169
db: ChEBI

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

2.1.1.42
type: BiochemicalReaction
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285191 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285192 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C057841 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285193 Cytosol/Stoichiometry/1.0
right: ferulic acid
right: S-adenosyl-L-homocysteine zwitterion
right: Hydrogen Ion
spontaneous: false
EC number: 2.1.1.42
left: S-adenosyl-L-methionine zwitterion
left: trans-caffeate
name: S-adenosyl-L-methionine zwitterion + trans-caffeate → Hydrogen Ion + S-adenosyl-L-homocysteine zwitterion + ferulic acid
conversion direction: LEFT_TO_RIGHT

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

Reference/CAS 92-61-5
type: UnificationXref
id: 92-61-5
db: CAS

6.2.1.12
type: BiochemicalReaction
participant stoichiometry: Compound/PW C285178 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 C285184 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285185 Cytosol/Stoichiometry/1.0
right: trans-4-coumaroyl-CoA
right: diphosphate(3−)
right: Adenosine monophosphate
spontaneous: false
EC number: 6.2.1.12
left: Adenosine triphosphate
left: Coenzyme A
left: trans-4-coumarate
name: Adenosine triphosphate + Coenzyme A + trans-4-coumarate → Adenosine monophosphate + diphosphate(3−) + trans-4-coumaroyl-CoA
conversion direction: LEFT_TO_RIGHT

Reference/ChEBI CHEBI 57770
type: UnificationXref
id: CHEBI:57770
db: ChEBI

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

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

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

Reference/UniProt Q9SZ46
type: UnificationXref
id: Q9SZ46
db: UniProt

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

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

Scopoletin 8-hydroxylase
type: Protein
cellular location: Cytosol
entity reference: Scopoletin 8-hydroxylase

Compound/PW C000032 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Adenosine monophosphate
stoichiometric coefficient: 1.0

Compound/PW C285194 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: trans-caffeoyl-CoA
stoichiometric coefficient: 1.0

Reference/ChemSpider 4444774
type: UnificationXref
id: 4444774
db: ChemSpider

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

Reference/ChEBI CHEBI 15422
type: UnificationXref
id: CHEBI:15422
db: ChEBI

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

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

1.14.14.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C104784 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285198 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285199 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000891 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001420 Cytosol/Stoichiometry/1.0
right: Hydrogen Ion
right: FMN
right: Sideretin
right: Water
spontaneous: false
EC number: 1.14.14.-
left: Oxygen
left: FMNH2
left: Fraxetin
name: FMNH2 + Fraxetin + Oxygen → FMN + Hydrogen Ion + Sideretin + Water
conversion direction: LEFT_TO_RIGHT

Reference/SMPDB SMP0729214
type: UnificationXref
id: SMP0729214
db: SMPDB

Reaction2146826
type: BiochemicalReaction
participant stoichiometry: Compound/PW C015392 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C012022 Cytosol/Stoichiometry/1.0
right: Scoparone
spontaneous: false
left: Scopoletin
name: Scopoletin → Scoparone
conversion direction: LEFT_TO_RIGHT

Arabidopsis thaliana
type: BioSource
xref: Reference/TAXONOMY 3702

1.14.11.60
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000134 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285198 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000174 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C015392 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001316 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Cytosol/Stoichiometry/1.0
right: Succinic acid
right: Carbon dioxide
right: Fraxetin
spontaneous: false
EC number: 1.14.11.60
left: Oxygen
left: Oxoglutaric acid
left: Scopoletin
name: Oxoglutaric acid + Oxygen + Scopoletin → Carbon dioxide + Fraxetin + Succinic acid
conversion direction: LEFT_TO_RIGHT

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

trans-4-coumarate
type: SmallMolecule
cellular location: Cytosol
entity reference: trans-4-coumarate

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

2.1.1.42
type: BiochemicalReaction
participant stoichiometry: Compound/PW C040034 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285192 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285193 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C015392 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285196 Cytosol/Stoichiometry/1.0
right: Scopoletin
right: S-adenosyl-L-homocysteine zwitterion
right: Hydrogen Ion
spontaneous: false
EC number: 2.1.1.42
left: S-adenosyl-L-methionine zwitterion
left: Esculetin
name: Esculetin + S-adenosyl-L-methionine zwitterion → Hydrogen Ion + S-adenosyl-L-homocysteine zwitterion + Scopoletin
conversion direction: LEFT_TO_RIGHT

Reaction2146825
type: BiochemicalReaction
participant stoichiometry: Compound/PW C015392 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285197 Cytosol/Stoichiometry/1.0
right: Scopoletin
spontaneous: true
left: trans-6-hydroxyferuloyl-CoA
name: trans-6-hydroxyferuloyl-CoA → Scopoletin
conversion direction: LEFT_TO_RIGHT

Reaction2146822
type: BiochemicalReaction
participant stoichiometry: Compound/PW C285194 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285196 Cytosol/Stoichiometry/1.0
right: Esculetin
spontaneous: false
left: trans-caffeoyl-CoA
name: trans-caffeoyl-CoA → Esculetin
conversion direction: LEFT_TO_RIGHT

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

1.14.11.61
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000134 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000174 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001316 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001065 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285197 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285195 Cytosol/Stoichiometry/1.0
right: trans-6-hydroxyferuloyl-CoA
right: Succinic acid
right: Carbon dioxide
spontaneous: false
EC number: 1.14.11.61
left: Oxygen
left: Oxoglutaric acid
left: trans-feruloyl-CoA(4−)
name: Oxoglutaric acid + Oxygen + trans-feruloyl-CoA(4−) → Carbon dioxide + Succinic acid + trans-6-hydroxyferuloyl-CoA
conversion direction: LEFT_TO_RIGHT

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

Reaction2146820
type: BiochemicalReaction
participant stoichiometry: Compound/PW C285178 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C285191 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 C285194 Cytosol/Stoichiometry/1.0
right: diphosphate(3−)
right: Adenosine monophosphate
right: trans-caffeoyl-CoA
spontaneous: false
left: trans-caffeate
left: Adenosine triphosphate
left: Coenzyme A
name: Adenosine triphosphate + Coenzyme A + trans-caffeate → Adenosine monophosphate + diphosphate(3−) + trans-caffeoyl-CoA
conversion direction: LEFT_TO_RIGHT

ChemicalStructure/PW C000032
type: ChemicalStructure
structure format: SMILES

Reaction2146821
type: BiochemicalReaction
participant stoichiometry: Compound/PW C285178 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001099 Cytosol/Stoichiometry/1.0
participant stoichiometry: Compound/PW C057841 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 C285195 Cytosol/Stoichiometry/1.0
right: diphosphate(3−)
right: Adenosine monophosphate
right: trans-feruloyl-CoA(4−)
spontaneous: false
left: Adenosine triphosphate
left: ferulic acid
left: Coenzyme A
name: Adenosine triphosphate + Coenzyme A + ferulic acid → Adenosine monophosphate + diphosphate(3−) + trans-feruloyl-CoA(4−)
conversion direction: LEFT_TO_RIGHT

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

Reference/KEGG Compound C09311
type: UnificationXref
id: C09311
db: KEGG Compound

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

Reference/KEGG Compound C00061
type: UnificationXref
id: C00061
db: KEGG Compound

Reference/ChEBI CHEBI 284936
type: UnificationXref
id: CHEBI:284936
db: ChEBI

FMNH2
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 16048
xref: Reference/BioCyc FMNH2
xref: Reference/KEGG Compound C01847
xref: Reference/PubChem-compound 445395
xref: Reference/CAS 5666-16-0
xref: Reference/ChemSpider 393046
xref: Reference/HMDB HMDB0001142
chemical formula: C17H23N4O9P
molecular weight: 458.12027
structure: ChemicalStructure/PW C000891

Reference/SMPDB SMP0002442
type: UnificationXref
id: SMP0002442
db: SMPDB

Reference/PubChem-compound 44229199
type: UnificationXref
id: 44229199
db: PubChem-compound

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

ChemicalStructure/PW C012022
type: ChemicalStructure
structure format: SMILES
structure data: COC1=C(OC)C=C2C=CC(=O)OC2=C1

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

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

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

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

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

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

S-adenosyl-L-homocysteine zwitterion
type: SmallMolecule
cellular location: Cytosol
entity reference: S-adenosyl-L-homocysteine zwitterion

ReactionCatalysis2178394
type: Catalysis
controller: Cytochrome P450 98A3
controlled: Reaction2146860
control type: ACTIVATION

Reference/ChEBI CHEBI 16526
type: UnificationXref
id: CHEBI:16526
db: ChEBI

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

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

Reference/KEGG Compound C09315
type: UnificationXref
id: C09315
db: KEGG Compound

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

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

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

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

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

Compound/PW C001420 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Water
stoichiometric coefficient: 1.0

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

Reference/ChEBI CHEBI 87136
type: UnificationXref
id: CHEBI:87136
db: ChEBI

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

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

Reference/KEGG Compound C01847
type: UnificationXref
id: C01847
db: KEGG Compound

Reference/ChemSpider 4444113
type: UnificationXref
id: 4444113
db: ChemSpider

Compound/PW C285197 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: trans-6-hydroxyferuloyl-CoA
stoichiometric coefficient: 1.0

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

ChemicalStructure/PW C000891
type: ChemicalStructure
structure format: SMILES

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

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

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

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

Reference/HMDB HMDB0030818
type: UnificationXref
id: HMDB0030818
db: HMDB

diphosphate(3−)
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 33019
chemical formula: HO7P2
molecular weight: 174.9214
structure: ChemicalStructure/PW C285178

Reference/HMDB HMDB0001142
type: UnificationXref
id: HMDB0001142
db: HMDB

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

Reference/ChemSpider 4573888
type: UnificationXref
id: 4573888
db: ChemSpider

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

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

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

Chloroplast
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0009507

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

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

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

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

Reference/PathWhiz PW002552
type: UnificationXref
id: PW002552
db: PathWhiz

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

phenylalanine ammonia lyase 1
type: Protein
cellular location: Cytosol
entity reference: phenylalanine ammonia lyase 1

Compound/PW C000891 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: FMNH2
stoichiometric coefficient: 1.0

ChemicalStructure/PW C000414
type: ChemicalStructure
structure format: SMILES

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

Compound/PW C012022 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: Scoparone
stoichiometric coefficient: 1.0

Compound/PW C285195 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: trans-feruloyl-CoA(4−)
stoichiometric coefficient: 1.0

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

Reference/PubChem-compound 280
type: UnificationXref
id: 280
db: PubChem-compound

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

Reference/ChEBI CHEBI 142095
type: UnificationXref
id: CHEBI:142095
db: ChEBI

4-coumarate--CoA ligase 4
type: ProteinReference
xref: Reference/UniProt Q9LU36
organism: Arabidopsis thaliana

Reference/CAS 1135-24-6
type: UnificationXref
id: 1135-24-6
db: CAS

Reference/UniProt Q9LE86
type: UnificationXref
id: Q9LE86
db: UniProt

ChemicalStructure/PW C011089
type: ChemicalStructure
structure format: SMILES
structure data: OC1=CC2=C(C=C1)C=CC(=O)O2

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

Reference/PubChem-compound 16741146
type: UnificationXref
id: 16741146
db: PubChem-compound

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

ChemicalStructure/PW C057841
type: ChemicalStructure
structure format: SMILES
structure data: COC1=CC(\C=C\C([O-])=O)=CC=C1O

ChemicalStructure/PW C000742
type: ChemicalStructure
structure format: SMILES
structure data: OC(=O)\C=C\C1=CC=CC=C1

Reference/BioCyc FMNH2
type: UnificationXref
id: FMNH2
db: BioCyc

trans-caffeate
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 57770
chemical formula: C9H7O4
molecular weight: 179.03499
structure: ChemicalStructure/PW C285191

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

S-adenosyl-L-methionine zwitterion
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 59789
chemical formula: C15H23N6O5S
molecular weight: 399.14505
structure: ChemicalStructure/PW C285192

Reference/ChEBI CHEBI 57856
type: UnificationXref
id: CHEBI:57856
db: ChEBI

Compound/PW C285193 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: S-adenosyl-L-homocysteine zwitterion
stoichiometric coefficient: 1.0

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

trans-6-hydroxyferuloyl-CoA
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 142390
chemical formula: C31H40N7O20P3S
molecular weight: 955.12836

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

Fraxetin
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 5169
chemical formula: C10H8O5
molecular weight: 208.03717
structure: ChemicalStructure/PW C285198

Reference/ChemSpider 393046
type: UnificationXref
id: 393046
db: ChemSpider

Sideretin
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 142095
chemical formula: C10H8O6
molecular weight: 224.03209

S-adenosyl-L-homocysteine zwitterion
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 57856
chemical formula: C14H20N6O5S
molecular weight: 384.12158
structure: ChemicalStructure/PW C285193

trans-caffeoyl-CoA
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 87136
chemical formula: C30H38N7O19P3S
molecular weight: 925.1178
structure: ChemicalStructure/PW C285194

trans-feruloyl-CoA(4−)
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 87305
chemical formula: C31H40N7O19P3S
molecular weight: 939.1334
structure: ChemicalStructure/PW C285195

Esculetin
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 490095
xref: Reference/PubChem-compound 5281416
chemical formula: C9H6O4
molecular weight: 178.02661
structure: ChemicalStructure/PW C285196

diphosphate(3−)
type: SmallMolecule
cellular location: Cytosol
entity reference: diphosphate(3−)

4-coumarate--CoA ligase 2
type: Protein
cellular location: Cytosol
entity reference: 4-coumarate--CoA ligase 2

trans-caffeate
type: SmallMolecule
cellular location: Cytosol
entity reference: trans-caffeate

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

Compound/PW C285192 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: S-adenosyl-L-methionine zwitterion
stoichiometric coefficient: 1.0

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

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

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

Reference/HMDB HMDB0001967
type: UnificationXref
id: HMDB0001967
db: HMDB

Reference/KEGG Compound C00423
type: UnificationXref
id: C00423
db: KEGG Compound

Scopoletin
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 17488
xref: Reference/ChemSpider 4444113
xref: Reference/CAS 92-61-5
xref: Reference/PubChem-compound 5280460
xref: Reference/HMDB HMDB0034344
xref: Reference/KEGG Compound C01752
chemical formula: C10H8O4
molecular weight: 192.04225
structure: ChemicalStructure/PW C015392

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

Compound/PW C285184 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: trans-4-coumarate
stoichiometric coefficient: 1.0

Reference/KEGG Compound C01752
type: UnificationXref
id: C01752
db: KEGG Compound

Compound/PW C285191 Cytosol/Stoichiometry/1.0
type: Stoichiometry
physical entity: trans-caffeate
stoichiometric coefficient: 1.0

Reference/ChEBI CHEBI 29749
type: UnificationXref
id: CHEBI:29749
db: ChEBI

Reference/ChEBI CHEBI 12876
type: UnificationXref
id: CHEBI:12876
db: ChEBI

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

trans-4-coumarate
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 12876
chemical formula: C9H7O3
molecular weight: 163.03952
structure: ChemicalStructure/PW C285184

trans-4-coumaroyl-CoA
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 85008
chemical formula: C30H38N7O18P3S
molecular weight: 909.12286