Arachidonic acid
type: SmallMoleculeReference
xref: Reference/CAS 506-32-1
xref: Reference/BioCyc ARACHIDONIC ACID
xref: Reference/ChEBI CHEBI 15843
xref: Reference/KEGG Compound C00219
xref: Reference/HMDB HMDB0001043
xref: Reference/ChemSpider 392692
xref: Reference/PubChem-compound 444899
chemical formula: C20H32O2
molecular weight: 304.24023
structure: ChemicalStructure/PW C000821

Reference/ChEBI CHEBI 15843
type: UnificationXref
id: CHEBI:15843
db: ChEBI

Compound/PW C001506 Endoplasmic Reticulum/Stoichiometry/1.0
type: Stoichiometry
physical entity: Adrenic acid
stoichiometric coefficient: 1.0

Reference/ChEBI CHEBI 77527
type: UnificationXref
id: CHEBI:77527
db: ChEBI

Reference/UniProt P0C871
type: UnificationXref
id: P0C871
db: UniProt

Reference/ChEBI CHEBI 77526
type: UnificationXref
id: CHEBI:77526
db: ChEBI

Reference/ChEBI CHEBI 28125
type: UnificationXref
id: CHEBI:28125
db: ChEBI

Reference/UniProt Q9EQC4
type: UnificationXref
id: Q9EQC4
db: UniProt

γ-Linolenic acid
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: γ-Linolenic acid

ChemicalStructure/PW C004252
type: ChemicalStructure
structure format: SMILES

Reference/ChEBI CHEBI 28364
type: UnificationXref
id: CHEBI:28364
db: ChEBI

Reference/CAS 24880-45-3
type: UnificationXref
id: 24880-45-3
db: CAS

Fatty acid desaturase 1
type: ProteinReference
xref: Reference/UniProt Q920L1
organism: Mus musculus

Linoleic acid
type: SmallMolecule
cellular location: Cytoplasm
entity reference: Linoleic acid

Reference/KEGG Compound C06428
type: UnificationXref
id: C06428
db: KEGG Compound

Reference/ChEBI CHEBI 17351
type: UnificationXref
id: CHEBI:17351
db: ChEBI

Reference/KEGG Compound C06429
type: UnificationXref
id: C06429
db: KEGG Compound

Reference/KEGG Compound C06426
type: UnificationXref
id: C06426
db: KEGG Compound

Reference/BioCyc CPD-7421
type: UnificationXref
id: CPD-7421
db: BioCyc

Reference/KEGG Compound C06427
type: UnificationXref
id: C06427
db: KEGG Compound

Reference/HMDB HMDB0006528
type: UnificationXref
id: HMDB0006528
db: HMDB

Reference/BioCyc D-HEXOSE-6-PHOSPHATE
type: UnificationXref
id: D-HEXOSE-6-PHOSPHATE
db: BioCyc

Reference/HMDB HMDB0001999
type: UnificationXref
id: HMDB0001999
db: HMDB

Compound/PW C004252 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z))
stoichiometric coefficient: 1.0

Compound/PW C002804 Endoplasmic Reticulum/Stoichiometry/1.0
type: Stoichiometry
physical entity: Stearidonic acid
stoichiometric coefficient: 1.0

Compound/PW C002718 Endoplasmic Reticulum/Stoichiometry/1.0
type: Stoichiometry
physical entity: Tetracosapentaenoic acid (24:5n-6)
stoichiometric coefficient: 1.0

Compound/PW C001736 Endoplasmic Reticulum/Stoichiometry/1.0
type: Stoichiometry
physical entity: 8,11,14-Eicosatrienoic acid
stoichiometric coefficient: 1.0

Reference/TAXONOMY 10090
type: UnificationXref
id: 10090
db: TAXONOMY

Reference/UniProt Q920L1
type: UnificationXref
id: Q920L1
db: UniProt

Arachidonic acid
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: Arachidonic acid

Reference/KEGG Compound C00219
type: UnificationXref
id: C00219
db: KEGG Compound

1.14.19.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001337 Endoplasmic Reticulum/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001466 Endoplasmic Reticulum/Stoichiometry/1.0
right: Eicosapentaenoic acid
spontaneous: false
EC number: 1.14.19.-
left: Cis-8,11,14,17-Eicosatetraenoic acid
name: Cis-8,11,14,17-Eicosatetraenoic acid → Eicosapentaenoic acid
conversion direction: LEFT_TO_RIGHT

Reference/CAS 506-26-3
type: UnificationXref
id: 506-26-3
db: CAS

2.3.1.199
type: BiochemicalReaction
participant stoichiometry: Compound/PW C002795 Endoplasmic Reticulum/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001337 Endoplasmic Reticulum/Stoichiometry/1.0
right: Docosapentaenoic acid (22n-3)
spontaneous: false
EC number: 2.3.1.199
left: Eicosapentaenoic acid
name: Eicosapentaenoic acid → Docosapentaenoic acid (22n-3)
conversion direction: LEFT_TO_RIGHT

Elongation of very long chain fatty acids protein 4
type: ProteinReference
xref: Reference/UniProt Q9EQC4
organism: Mus musculus

Eicosapentaenoic acid
type: SmallMoleculeReference
xref: Reference/CAS 10417-94-4
xref: Reference/PubChem-compound 446284
xref: Reference/HMDB HMDB0001999
xref: Reference/BioCyc CPD-6941
xref: Reference/KEGG Compound C06428
xref: Reference/ChemSpider 393682
xref: Reference/ChEBI CHEBI 28364
chemical formula: C20H30O2
molecular weight: 302.22458
structure: ChemicalStructure/PW C001337

1.14.19.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000530 Endoplasmic Reticulum/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001772 Endoplasmic Reticulum/Stoichiometry/1.0
right: γ-Linolenic acid
spontaneous: false
EC number: 1.14.19.-
left: Linoleic acid
name: Linoleic acid → γ-Linolenic acid
conversion direction: LEFT_TO_RIGHT

2.3.1.199
type: BiochemicalReaction
participant stoichiometry: Compound/PW C002795 Endoplasmic Reticulum/Stoichiometry/1.0
participant stoichiometry: Compound/PW C002719 Endoplasmic Reticulum/Stoichiometry/1.0
right: Tetracosapentaenoic acid (24:5n-3)
spontaneous: false
EC number: 2.3.1.199
left: Docosapentaenoic acid (22n-3)
name: Docosapentaenoic acid (22n-3) → Tetracosapentaenoic acid (24:5n-3)
conversion direction: LEFT_TO_RIGHT

PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z))
type: SmallMolecule
cellular location: Cytoplasm
entity reference: PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z))

Reference/HMDB HMDB0000673
type: UnificationXref
id: HMDB0000673
db: HMDB

Docosapentaenoic acid (22n-3)
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0006528
xref: Reference/ChEBI CHEBI 53488
xref: Reference/PubChem-compound 5497182
xref: Reference/ChemSpider 4593750
xref: Reference/KEGG Compound C16513
xref: Reference/CAS 24880-45-3
chemical formula: C22H34O2
molecular weight: 330.2559
structure: ChemicalStructure/PW C002795

Fatty Acid Metabolism
type: Pathway
pathway order: SubPathwayInteractionSteps/SubPathway107909
pathway order: SubPathwayInteractionSteps/SubPathway107910
pathway component: SubPathwayInteraction107910
pathway component: SubPathwayInteraction107909
xref: Reference/SMPDB SMP0000051
xref: Reference/PathWhiz PW000023
name: SubPathway

Tetracosahexaenoic acid
type: SmallMoleculeReference
xref: Reference/PubChem-compound 11792612
xref: Reference/CAS 81247-23-6
xref: Reference/ChEBI CHEBI 77366
xref: Reference/HMDB HMDB0002007
xref: Reference/ChemSpider 9967286
chemical formula: C24H36O2
molecular weight: 356.27155
structure: ChemicalStructure/PW C001344

Cis-8,11,14,17-Eicosatetraenoic acid
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 71488
xref: Reference/ChemSpider 9897310
xref: Reference/PubChem-compound 11722594
xref: Reference/HMDB HMDB0002177
xref: Reference/CAS 24880-40-8
chemical formula: C20H32O2
molecular weight: 304.24023
structure: ChemicalStructure/PW C001466

Tetracosatetraenoic acid (24:4n-6)
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: Tetracosatetraenoic acid (24:4n-6)

Compound/PW C002719 Endoplasmic Reticulum/Stoichiometry/1.0
type: Stoichiometry
physical entity: Tetracosapentaenoic acid (24:5n-3)
stoichiometric coefficient: 1.0

Reference/UniProt Q9Z0R9
type: UnificationXref
id: Q9Z0R9
db: UniProt

Reference/HMDB HMDB0002177
type: UnificationXref
id: HMDB0002177
db: HMDB

Fatty acid desaturase 2
type: ProteinReference
xref: Reference/UniProt Q9Z0R9
organism: Mus musculus

Linoleic acid
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: Linoleic acid

Cytosolic phospholipase A2 beta
type: ProteinReference
xref: Reference/UniProt P0C871
organism: Mus musculus

Reference/PubChem-compound 52922845
type: UnificationXref
id: 52922845
db: PubChem-compound

Reference/CAS 10417-94-4
type: UnificationXref
id: 10417-94-4
db: CAS

Docosahexaenoic acid
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 28125
xref: Reference/ChemSpider 393183
xref: Reference/PubChem-compound 445580
xref: Reference/BioCyc D-HEXOSE-6-PHOSPHATE
xref: Reference/CAS 6217-54-5
xref: Reference/KEGG Compound C06429
xref: Reference/HMDB HMDB0002183
chemical formula: C22H32O2
molecular weight: 328.24023
structure: ChemicalStructure/PW C001472

Reference/HMDB HMDB0006547
type: UnificationXref
id: HMDB0006547
db: HMDB

Tetracosatetraenoic acid (24:4n-6)
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0006246
xref: Reference/PubChem-compound 52921800
xref: Reference/ChemSpider 30776538
xref: Reference/ChEBI CHEBI 77526
chemical formula: C24H40O2
molecular weight: 360.30283
structure: ChemicalStructure/PW C002686

ChemicalStructure/PW C001772
type: ChemicalStructure
structure format: SMILES
structure data: CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O

Mus musculus
type: BioSource
xref: Reference/TAXONOMY 10090

Reference/HMDB HMDB0002183
type: UnificationXref
id: HMDB0002183
db: HMDB

Reference/PubChem-compound 5280934
type: UnificationXref
id: 5280934
db: PubChem-compound

Reference/PubChem-compound 5280933
type: UnificationXref
id: 5280933
db: PubChem-compound

Reference/CAS 28874-58-0
type: UnificationXref
id: 28874-58-0
db: CAS

Reference/ChemSpider 4444199
type: UnificationXref
id: 4444199
db: ChemSpider

Reference/BioCyc CPD-4223
type: UnificationXref
id: CPD-4223
db: BioCyc

Compound/PW C001073 Endoplasmic Reticulum/Stoichiometry/1.0
type: Stoichiometry
physical entity: α-Linolenic acid
stoichiometric coefficient: 1.0

ReactionCatalysis99968
type: Catalysis
controller: Elongation of very long chain fatty acids protein 5
controlled: 2.3.1.199
control type: ACTIVATION

ReactionCatalysis99969
type: Catalysis
controller: Fatty acid desaturase 1
controlled: 1.14.19.-
control type: ACTIVATION

Reference/BioCyc 5Z13E-15S-91115-TRIHYDROXYPROSTA-
type: UnificationXref
id: 5Z13E-15S-91115-TRIHYDROXYPROSTA-
db: BioCyc

ChemicalStructure/PW C001337
type: ChemicalStructure
structure format: SMILES
structure data: CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

ReactionCatalysis99967
type: Catalysis
controller: Fatty acid desaturase 2
controlled: 1.14.19.-
control type: ACTIVATION

Stearidonic acid
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0006547
xref: Reference/CAS 20290-75-9
xref: Reference/PubChem-compound 5312508
xref: Reference/ChEBI CHEBI 32389
xref: Reference/KEGG Compound C16300
xref: Reference/ChemSpider 4471933
chemical formula: C18H28O2
molecular weight: 276.20892
structure: ChemicalStructure/PW C002804

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

ChemicalStructure/PW C002795
type: ChemicalStructure
structure format: SMILES
structure data: CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O

ReactionCatalysis99971
type: Catalysis
controller: Fatty acid desaturase 2
controlled: 1.14.19.-
control type: ACTIVATION

ReactionCatalysis99972
type: Catalysis
controller: Elongation of very long chain fatty acids protein 4
controlled: 2.3.1.199
control type: ACTIVATION

ReactionCatalysis99970
type: Catalysis
controller: Elongation of very long chain fatty acids protein 5
controlled: 2.3.1.199
control type: ACTIVATION

Linoleic acid
type: SmallMolecule
cellular location: Extracellular Space
entity reference: Linoleic acid

ChemicalStructure/PW C001466
type: ChemicalStructure
structure format: SMILES
structure data: CC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(O)=O

ChemicalStructure/PW C001344
type: ChemicalStructure
structure format: SMILES
structure data: CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O

Reference/CAS 25448-00-4
type: UnificationXref
id: 25448-00-4
db: CAS

Elongation of very long chain fatty acids protein 4
type: Protein
cellular location: Endoplasmic Reticulum
entity reference: Elongation of very long chain fatty acids protein 4

Compound/PW C000821 Endoplasmic Reticulum/Stoichiometry/1.0
type: Stoichiometry
physical entity: Arachidonic acid
stoichiometric coefficient: 1.0

ReactionCatalysis99979
type: Catalysis
controller: Cytosolic phospholipase A2 beta
controlled: 3.1.1.4
control type: ACTIVATION

ReactionCatalysis99977
type: Catalysis
controller: Elongation of very long chain fatty acids protein 4
controlled: 2.3.1.199
control type: ACTIVATION

ReactionCatalysis99978
type: Catalysis
controller: Fatty acid desaturase 2
controlled: 1.14.19.-
control type: ACTIVATION

ReactionCatalysis99975
type: Catalysis
controller: Fatty acid desaturase 1
controlled: 1.14.19.-
control type: ACTIVATION

ReactionCatalysis99976
type: Catalysis
controller: Elongation of very long chain fatty acids protein 5
controlled: 2.3.1.199
control type: ACTIVATION

ReactionCatalysis99973
type: Catalysis
controller: Fatty acid desaturase 2
controlled: 1.14.19.-
control type: ACTIVATION

ReactionCatalysis99974
type: Catalysis
controller: Elongation of very long chain fatty acids protein 5
controlled: 2.3.1.199
control type: ACTIVATION

ChemicalStructure/PW C002686
type: ChemicalStructure
structure format: SMILES
structure data: CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O

Reference/SMPDB SMP0000051
type: UnificationXref
id: SMP0000051
db: SMPDB

ChemicalStructure/PW C001472
type: ChemicalStructure
structure format: SMILES
structure data: CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O

Reference/GENE ONTOLOGY GO 0005759
type: UnificationXref
id: GO:0005759
db: GENE ONTOLOGY

1.14.19.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001073 Endoplasmic Reticulum/Stoichiometry/1.0
participant stoichiometry: Compound/PW C002804 Endoplasmic Reticulum/Stoichiometry/1.0
right: Stearidonic acid
spontaneous: false
EC number: 1.14.19.-
left: α-Linolenic acid
name: α-Linolenic acid → Stearidonic acid
conversion direction: LEFT_TO_RIGHT

Reference/PubChem-compound 14505435
type: UnificationXref
id: 14505435
db: PubChem-compound

2.3.1.199
type: BiochemicalReaction
participant stoichiometry: Compound/PW C002804 Endoplasmic Reticulum/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001466 Endoplasmic Reticulum/Stoichiometry/1.0
right: Cis-8,11,14,17-Eicosatetraenoic acid
spontaneous: false
EC number: 2.3.1.199
left: Stearidonic acid
name: Stearidonic acid → Cis-8,11,14,17-Eicosatetraenoic acid
conversion direction: LEFT_TO_RIGHT

Reference/HMDB HMDB0006322
type: UnificationXref
id: HMDB0006322
db: HMDB

Reference/HMDB HMDB0006323
type: UnificationXref
id: HMDB0006323
db: HMDB

α-Linolenic acid
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: α-Linolenic acid

Reference/ChemSpider 9897310
type: UnificationXref
id: 9897310
db: ChemSpider

Docosapentaenoic acid (22n-3)
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: Docosapentaenoic acid (22n-3)

Reference/PubChem-compound 5280581
type: UnificationXref
id: 5280581
db: PubChem-compound

Reference/BioCyc CPD-7196
type: UnificationXref
id: CPD-7196
db: BioCyc

Reference/PubChem-compound 444899
type: UnificationXref
id: 444899
db: PubChem-compound

Stearidonic acid
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: Stearidonic acid

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

Compound/PW C000530 Extracellular Space/Stoichiometry/1.0
type: Stoichiometry
physical entity: Linoleic acid
stoichiometric coefficient: 1.0

Eicosapentaenoic acid
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: Eicosapentaenoic acid

Reference/ChemSpider 4593750
type: UnificationXref
id: 4593750
db: ChemSpider

ChemicalStructure/PW C001322
type: ChemicalStructure
structure format: SMILES
structure data: CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O

Reference/ChemSpider 4945614
type: UnificationXref
id: 4945614
db: ChemSpider

Compound/PW C002686 Endoplasmic Reticulum/Stoichiometry/1.0
type: Stoichiometry
physical entity: Tetracosatetraenoic acid (24:4n-6)
stoichiometric coefficient: 1.0

Reference/ChemSpider 393682
type: UnificationXref
id: 393682
db: ChemSpider

Cytosolic phospholipase A2 beta
type: Protein
cellular location: Cytoplasm
entity reference: Cytosolic phospholipase A2 beta

Reference/PubChem-compound 446284
type: UnificationXref
id: 446284
db: PubChem-compound

Reference/PubChem-compound 5497182
type: UnificationXref
id: 5497182
db: PubChem-compound

Reference/PubChem-compound 5497181
type: UnificationXref
id: 5497181
db: PubChem-compound

Alpha Linolenic Acid and Linoleic Acid Metabolism
type: Pathway
pathway order: PathwayEnzymeReaction/2110830
pathway order: PathwayEnzymeReaction/2110840
pathway order: PathwaySubPathway/107910
pathway order: PathwayEnzymeReaction/2110832
pathway order: PathwayEnzymeReaction/2110831
pathway order: PathwayEnzymeReaction/2110834
pathway order: PathwayEnzymeReaction/2110833
pathway order: PathwayTransport/2110842
pathway order: PathwayEnzymeReaction/2110836
pathway order: PathwayTransport/2110841
pathway order: PathwayEnzymeReaction/2110835
pathway order: PathwayEnzymeReaction/2110838
pathway order: PathwayEnzymeReaction/2110837
pathway order: PathwayEnzymeReaction/2110829
pathway order: PathwayEnzymeReaction/2110828
pathway order: PathwayEnzymeReaction/2110839
pathway order: PathwaySubPathway/107909
pathway component: ReactionCatalysis99968
pathway component: 1.14.19.-
pathway component: ReactionCatalysis99969
pathway component: 2.3.1.199
pathway component: ReactionCatalysis99967
pathway component: Transport1039
pathway component: ReactionCatalysis99971
pathway component: ReactionCatalysis99972
pathway component: ReactionCatalysis99970
pathway component: Fatty Acid Metabolism
pathway component: Transport1040
pathway component: 3.1.1.4
pathway component: ReactionCatalysis99979
pathway component: ReactionCatalysis99977
pathway component: ReactionCatalysis99978
pathway component: ReactionCatalysis99975
pathway component: ReactionCatalysis99976
pathway component: ReactionCatalysis99973
pathway component: ReactionCatalysis99974
xref: Reference/PathWhiz PW064568
xref: Reference/SMPDB SMP0063593
organism: Mus musculus

Reference/KEGG Compound C01595
type: UnificationXref
id: C01595
db: KEGG Compound

Reference/PubChem-compound 5280450
type: UnificationXref
id: 5280450
db: PubChem-compound

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

Reference/GENE ONTOLOGY GO 0005737
type: UnificationXref
id: GO:0005737
db: GENE ONTOLOGY

α-Linolenic acid
type: SmallMolecule
cellular location: Cytoplasm
entity reference: α-Linolenic acid

Elongation of very long chain fatty acids protein 5
type: Protein
cellular location: Endoplasmic Reticulum
entity reference: Elongation of very long chain fatty acids protein 5

Reference/HMDB HMDB0003073
type: UnificationXref
id: HMDB0003073
db: HMDB

Reference/ChemSpider 4593749
type: UnificationXref
id: 4593749
db: ChemSpider

Endoplasmic Reticulum
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0005783

Reference/ChemSpider 4471933
type: UnificationXref
id: 4471933
db: ChemSpider

Reference/KEGG Compound C00157
type: UnificationXref
id: C00157
db: KEGG Compound

Reference/PathWhiz PW064568
type: UnificationXref
id: PW064568
db: PathWhiz

Reference/ChEBI CHEBI 27432
type: UnificationXref
id: CHEBI:27432
db: ChEBI

Docosahexaenoic acid
type: SmallMolecule
cellular location: Mitochondrial Matrix
entity reference: Docosahexaenoic acid
name: SubPathwayOutput

Mitochondrial Matrix
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0005759

Reference/ChemSpider 4444436
type: UnificationXref
id: 4444436
db: ChemSpider

Reference/ChemSpider 392692
type: UnificationXref
id: 392692
db: ChemSpider

Reference/ChemSpider 4444437
type: UnificationXref
id: 4444437
db: ChemSpider

Compound/PW C001073 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: α-Linolenic acid
stoichiometric coefficient: 1.0

Compound/PW C000530 Cytoplasm/Stoichiometry/1.0
type: Stoichiometry
physical entity: Linoleic acid
stoichiometric coefficient: 1.0

Reference/ChEBI CHEBI 77366
type: UnificationXref
id: CHEBI:77366
db: ChEBI

Reference/BioCyc LINOLENIC ACID
type: UnificationXref
id: LINOLENIC_ACID
db: BioCyc

γ-Linolenic acid
type: SmallMoleculeReference
xref: Reference/CAS 506-26-3
xref: Reference/BioCyc 5Z13E-15S-91115-TRIHYDROXYPROSTA-
xref: Reference/HMDB HMDB0003073
xref: Reference/KEGG Compound C06426
xref: Reference/ChemSpider 4444436
xref: Reference/ChEBI CHEBI 28661
xref: Reference/PubChem-compound 5280933
chemical formula: C18H30O2
molecular weight: 278.22458
structure: ChemicalStructure/PW C001772

Reference/ChEBI CHEBI 77360
type: UnificationXref
id: CHEBI:77360
db: ChEBI

Reference/HMDB HMDB0006246
type: UnificationXref
id: HMDB0006246
db: HMDB

Cytoplasm
type: CellularLocationVocabulary
xref: Reference/GENE ONTOLOGY GO 0005737

Docosapentaenoic acid (22n-6)
type: SmallMolecule
cellular location: Mitochondrial Matrix
entity reference: Docosapentaenoic acid (22n-6)
name: SubPathwayOutput

Compound/PW C001466 Endoplasmic Reticulum/Stoichiometry/1.0
type: Stoichiometry
physical entity: Cis-8,11,14,17-Eicosatetraenoic acid
stoichiometric coefficient: 1.0

ChemicalStructure/PW C000821
type: ChemicalStructure
structure format: SMILES
structure data: CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

8,11,14-Eicosatrienoic acid
type: SmallMoleculeReference
xref: Reference/ChemSpider 4444199
xref: Reference/CAS 1783-84-2
xref: Reference/KEGG Compound C03242
xref: Reference/PubChem-compound 5280581
xref: Reference/HMDB HMDB0002925
xref: Reference/BioCyc CPD-7196
xref: Reference/ChEBI CHEBI 53486
chemical formula: C20H34O2
molecular weight: 306.2559
structure: ChemicalStructure/PW C001736

Reference/KEGG Compound C16513
type: UnificationXref
id: C16513
db: KEGG Compound

Linoleic acid
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0000673
xref: Reference/ChemSpider 4444105
xref: Reference/CAS 60-33-3
xref: Reference/KEGG Compound C01595
xref: Reference/PubChem-compound 5280450
xref: Reference/ChEBI CHEBI 17351
chemical formula: C18H32O2
molecular weight: 280.24023
structure: ChemicalStructure/PW C000530

Reference/GENE ONTOLOGY GO 0005783
type: UnificationXref
id: GO:0005783
db: GENE ONTOLOGY

Tetracosapentaenoic acid (24:5n-6)
type: SmallMoleculeReference
xref: Reference/BioCyc CPD-4223
xref: Reference/ChemSpider 30776541
xref: Reference/PubChem-compound 14505435
xref: Reference/HMDB HMDB0006322
xref: Reference/ChEBI CHEBI 77527
chemical formula: C24H38O2
molecular weight: 358.28717
structure: ChemicalStructure/PW C002718

Reference/SMPDB SMP0063593
type: UnificationXref
id: SMP0063593
db: SMPDB

Tetracosapentaenoic acid (24:5n-3)
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0006323
xref: Reference/ChEBI CHEBI 77360
xref: Reference/BioCyc CPD-7421
xref: Reference/PubChem-compound 52921801
xref: Reference/ChemSpider 30776540
chemical formula: C24H38O2
molecular weight: 358.28717
structure: ChemicalStructure/PW C002719

8,11,14-Eicosatrienoic acid
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: 8,11,14-Eicosatrienoic acid

Reference/CAS 1783-84-2
type: UnificationXref
id: 1783-84-2
db: CAS

Adrenic acid
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: Adrenic acid

Adrenic acid
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0002226
xref: Reference/PubChem-compound 5497181
xref: Reference/KEGG Compound C16527
xref: Reference/ChemSpider 4593749
xref: Reference/CAS 28874-58-0
xref: Reference/ChEBI CHEBI 53487
chemical formula: C22H36O2
molecular weight: 332.27155
structure: ChemicalStructure/PW C001506

Compound/PW C001344 Endoplasmic Reticulum/Stoichiometry/1.0
type: Stoichiometry
physical entity: Tetracosahexaenoic acid
stoichiometric coefficient: 1.0

Reference/HMDB HMDB0002226
type: UnificationXref
id: HMDB0002226
db: HMDB

Tetracosapentaenoic acid (24:5n-6)
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: Tetracosapentaenoic acid (24:5n-6)
name: SubPathwayInput

Cis-8,11,14,17-Eicosatetraenoic acid
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: Cis-8,11,14,17-Eicosatetraenoic acid

Reference/CAS 60-33-3
type: UnificationXref
id: 60-33-3
db: CAS

Reference/HMDB HMDB0008204
type: UnificationXref
id: HMDB0008204
db: HMDB

Reference/KEGG Compound C16527
type: UnificationXref
id: C16527
db: KEGG Compound

α-Linolenic acid
type: SmallMoleculeReference
xref: Reference/HMDB HMDB0001388
xref: Reference/ChEBI CHEBI 27432
xref: Reference/BioCyc LINOLENIC ACID
xref: Reference/CAS 463-40-1
xref: Reference/KEGG Compound C06427
xref: Reference/PubChem-compound 5280934
xref: Reference/ChemSpider 4444437
chemical formula: C18H30O2
molecular weight: 278.22458
structure: ChemicalStructure/PW C001073

Reference/PathWhiz PW000023
type: UnificationXref
id: PW000023
db: PathWhiz

Reference/PubChem-compound 11792612
type: UnificationXref
id: 11792612
db: PubChem-compound

Compound/PW C000530 Endoplasmic Reticulum/Stoichiometry/1.0
type: Stoichiometry
physical entity: Linoleic acid
stoichiometric coefficient: 1.0

SubPathwayInteraction107909
type: Interaction
name: SubPathwayReaction
name: SubPathway107909Reaction
participant: Docosahexaenoic acid
participant: Tetracosahexaenoic acid

Reference/PubChem-compound 52921800
type: UnificationXref
id: 52921800
db: PubChem-compound

Reference/ChEBI CHEBI 32389
type: UnificationXref
id: CHEBI:32389
db: ChEBI

Reference/PubChem-compound 52921801
type: UnificationXref
id: 52921801
db: PubChem-compound

Elongation of very long chain fatty acids protein 5
type: ProteinReference
xref: Reference/UniProt Q8BHI7
organism: Mus musculus

Reference/ChEBI CHEBI 53486
type: UnificationXref
id: CHEBI:53486
db: ChEBI

ChemicalStructure/PW C001736
type: ChemicalStructure
structure format: SMILES
structure data: CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O

Reference/ChEBI CHEBI 53487
type: UnificationXref
id: CHEBI:53487
db: ChEBI

Reference/HMDB HMDB0001388
type: UnificationXref
id: HMDB0001388
db: HMDB

Reference/ChemSpider 393183
type: UnificationXref
id: 393183
db: ChemSpider

Fatty acid desaturase 2
type: Protein
cellular location: Endoplasmic Reticulum
entity reference: Fatty acid desaturase 2

Reference/PubChem-compound 6441454
type: UnificationXref
id: 6441454
db: PubChem-compound

ChemicalStructure/PW C000530
type: ChemicalStructure
structure format: SMILES
structure data: CCCCC\C=C/C\C=C/CCCCCCCC(O)=O

Docosapentaenoic acid (22n-6)
type: SmallMoleculeReference
xref: Reference/ChEBI CHEBI 65136
xref: Reference/PubChem-compound 6441454
xref: Reference/HMDB HMDB0001976
xref: Reference/CAS 25448-00-4
xref: Reference/ChemSpider 4945614
chemical formula: C22H34O2
molecular weight: 330.2559
structure: ChemicalStructure/PW C001322

Reference/CAS 6217-54-5
type: UnificationXref
id: 6217-54-5
db: CAS

Reference/ChemSpider 9967286
type: UnificationXref
id: 9967286
db: ChemSpider

Reference/UniProt Q8BHI7
type: UnificationXref
id: Q8BHI7
db: UniProt

Reference/CAS 81247-23-6
type: UnificationXref
id: 81247-23-6
db: CAS

Tetracosahexaenoic acid
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: Tetracosahexaenoic acid
name: SubPathwayInput

Reference/ChemSpider 4444105
type: UnificationXref
id: 4444105
db: ChemSpider

ChemicalStructure/PW C002719
type: ChemicalStructure
structure format: SMILES
structure data: CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O

Reference/ChemSpider 30776541
type: UnificationXref
id: 30776541
db: ChemSpider

Reference/CAS 20290-75-9
type: UnificationXref
id: 20290-75-9
db: CAS

Compound/PW C001337 Endoplasmic Reticulum/Stoichiometry/1.0
type: Stoichiometry
physical entity: Eicosapentaenoic acid
stoichiometric coefficient: 1.0

Compound/PW C001772 Endoplasmic Reticulum/Stoichiometry/1.0
type: Stoichiometry
physical entity: γ-Linolenic acid
stoichiometric coefficient: 1.0

Reference/PubChem-compound 5312508
type: UnificationXref
id: 5312508
db: PubChem-compound

ChemicalStructure/PW C002718
type: ChemicalStructure
structure format: SMILES
structure data: CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O

ChemicalStructure/PW C001506
type: ChemicalStructure
structure format: SMILES
structure data: CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O

Reference/ChEBI CHEBI 53488
type: UnificationXref
id: CHEBI:53488
db: ChEBI

Reference/KEGG Compound C03242
type: UnificationXref
id: C03242
db: KEGG Compound

Reference/HMDB HMDB0002007
type: UnificationXref
id: HMDB0002007
db: HMDB

Reference/KEGG Compound C16300
type: UnificationXref
id: C16300
db: KEGG Compound

ChemicalStructure/PW C001073
type: ChemicalStructure
structure format: SMILES
structure data: CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O

Reference/PubChem-compound 445580
type: UnificationXref
id: 445580
db: PubChem-compound

Reference/BioCyc CPD-6941
type: UnificationXref
id: CPD-6941
db: BioCyc

α-Linolenic acid
type: SmallMolecule
cellular location: Extracellular Space
entity reference: α-Linolenic acid

Reference/ChEBI CHEBI 71488
type: UnificationXref
id: CHEBI:71488
db: ChEBI

ChemicalStructure/PW C002804
type: ChemicalStructure
structure format: SMILES
structure data: CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O

Reference/HMDB HMDB0002925
type: UnificationXref
id: HMDB0002925
db: HMDB

Reference/ChemSpider 30776538
type: UnificationXref
id: 30776538
db: ChemSpider

Transport1039
type: Transport
participant stoichiometry: Compound/PW C001073 Extracellular Space/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001073 Cytoplasm/Stoichiometry/1.0
right: α-Linolenic acid
spontaneous: false
left: α-Linolenic acid
name: α-Linolenic acid (→) Transport: Mus musculus, Extracellular Space to Mus musculus, Cell, Cytoplasm
conversion direction: LEFT_TO_RIGHT

Fatty acid desaturase 1
type: Protein
cellular location: Endoplasmic Reticulum
entity reference: Fatty acid desaturase 1

Compound/PW C001073 Extracellular Space/Stoichiometry/1.0
type: Stoichiometry
physical entity: α-Linolenic acid
stoichiometric coefficient: 1.0

Reference/ChemSpider 30776540
type: UnificationXref
id: 30776540
db: ChemSpider

Transport1040
type: Transport
participant stoichiometry: Compound/PW C000530 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000530 Extracellular Space/Stoichiometry/1.0
right: Linoleic acid
spontaneous: false
left: Linoleic acid
name: Linoleic acid (→) Transport: Mus musculus, Extracellular Space to Mus musculus, Cell, Cytoplasm
conversion direction: LEFT_TO_RIGHT

Reference/HMDB HMDB0001043
type: UnificationXref
id: HMDB0001043
db: HMDB

Reference/CAS 24880-40-8
type: UnificationXref
id: 24880-40-8
db: CAS

Reference/ChEBI CHEBI 28661
type: UnificationXref
id: CHEBI:28661
db: ChEBI

PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z))
type: SmallMoleculeReference
xref: Reference/ChemSpider 24766866
xref: Reference/HMDB HMDB0008204
xref: Reference/PubChem-compound 52922845
xref: Reference/KEGG Compound C00157
xref: Reference/BioCyc PHOSPHATIDYLCHOLINE
chemical formula: C44H78NO8P
molecular weight: 779.5465
structure: ChemicalStructure/PW C004252

2.3.1.199
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001506 Endoplasmic Reticulum/Stoichiometry/1.0
participant stoichiometry: Compound/PW C002686 Endoplasmic Reticulum/Stoichiometry/1.0
right: Tetracosatetraenoic acid (24:4n-6)
spontaneous: false
EC number: 2.3.1.199
left: Adrenic acid
name: Adrenic acid → Tetracosatetraenoic acid (24:4n-6)
conversion direction: LEFT_TO_RIGHT

Reference/ChEBI CHEBI 65136
type: UnificationXref
id: CHEBI:65136
db: ChEBI

Compound/PW C002795 Endoplasmic Reticulum/Stoichiometry/1.0
type: Stoichiometry
physical entity: Docosapentaenoic acid (22n-3)
stoichiometric coefficient: 1.0

Reference/CAS 506-32-1
type: UnificationXref
id: 506-32-1
db: CAS

1.14.19.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C002718 Endoplasmic Reticulum/Stoichiometry/1.0
participant stoichiometry: Compound/PW C002686 Endoplasmic Reticulum/Stoichiometry/1.0
right: Tetracosapentaenoic acid (24:5n-6)
spontaneous: false
EC number: 1.14.19.-
left: Tetracosatetraenoic acid (24:4n-6)
name: Tetracosatetraenoic acid (24:4n-6) → Tetracosapentaenoic acid (24:5n-6)
conversion direction: LEFT_TO_RIGHT

3.1.1.4
type: BiochemicalReaction
participant stoichiometry: Compound/PW C004252 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001073 Cytoplasm/Stoichiometry/1.0
participant stoichiometry: Compound/PW C000530 Cytoplasm/Stoichiometry/1.0
right: Linoleic acid
right: α-Linolenic acid
spontaneous: false
EC number: 3.1.1.4
left: PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z))
name: PC(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) → Linoleic acid + α-Linolenic acid
conversion direction: LEFT_TO_RIGHT

Reference/CAS 463-40-1
type: UnificationXref
id: 463-40-1
db: CAS

SubPathwayInteraction107910
type: Interaction
name: SubPathwayReaction
name: SubPathway107910Reaction
participant: Tetracosapentaenoic acid (24:5n-6)
participant: Docosapentaenoic acid (22n-6)

Reference/ChemSpider 24766866
type: UnificationXref
id: 24766866
db: ChemSpider

Reference/PubChem-compound 11722594
type: UnificationXref
id: 11722594
db: PubChem-compound

1.14.19.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001344 Endoplasmic Reticulum/Stoichiometry/1.0
participant stoichiometry: Compound/PW C002719 Endoplasmic Reticulum/Stoichiometry/1.0
right: Tetracosahexaenoic acid
spontaneous: false
EC number: 1.14.19.-
left: Tetracosapentaenoic acid (24:5n-3)
name: Tetracosapentaenoic acid (24:5n-3) → Tetracosahexaenoic acid
conversion direction: LEFT_TO_RIGHT

2.3.1.199
type: BiochemicalReaction
participant stoichiometry: Compound/PW C001772 Endoplasmic Reticulum/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001736 Endoplasmic Reticulum/Stoichiometry/1.0
right: 8,11,14-Eicosatrienoic acid
spontaneous: false
EC number: 2.3.1.199
left: γ-Linolenic acid
name: γ-Linolenic acid → 8,11,14-Eicosatrienoic acid
conversion direction: LEFT_TO_RIGHT

1.14.19.-
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000821 Endoplasmic Reticulum/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001736 Endoplasmic Reticulum/Stoichiometry/1.0
right: Arachidonic acid
spontaneous: false
EC number: 1.14.19.-
left: 8,11,14-Eicosatrienoic acid
name: 8,11,14-Eicosatrienoic acid → Arachidonic acid
conversion direction: LEFT_TO_RIGHT

2.3.1.199
type: BiochemicalReaction
participant stoichiometry: Compound/PW C000821 Endoplasmic Reticulum/Stoichiometry/1.0
participant stoichiometry: Compound/PW C001506 Endoplasmic Reticulum/Stoichiometry/1.0
right: Adrenic acid
spontaneous: false
EC number: 2.3.1.199
left: Arachidonic acid
name: Arachidonic acid → Adrenic acid
conversion direction: LEFT_TO_RIGHT

Reference/BioCyc ARACHIDONIC ACID
type: UnificationXref
id: ARACHIDONIC_ACID
db: BioCyc

Reference/HMDB HMDB0001976
type: UnificationXref
id: HMDB0001976
db: HMDB

Tetracosapentaenoic acid (24:5n-3)
type: SmallMolecule
cellular location: Endoplasmic Reticulum
entity reference: Tetracosapentaenoic acid (24:5n-3)