CHEBI:28661 - γ-linolenic acid

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ChEBI Name γ-linolenic acid
ChEBI ID CHEBI:28661
ChEBI ASCII Name gamma-linolenic acid
Definition A C18, ω-6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:24197, CHEBI:10573
Supplier Information ChemicalBook:CB3238150, eMolecules:524834, ZINC000003777423
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Formula C18H30O2
Net Charge 0
Average Mass 278.42960
Monoisotopic Mass 278.22458
InChI InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-
InChIKey VZCCETWTMQHEPK-QNEBEIHSSA-N
SMILES CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
(via linolenic acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing γ-linolenic acid (CHEBI:28661) has role human metabolite (CHEBI:77746)
γ-linolenic acid (CHEBI:28661) has role mouse metabolite (CHEBI:75771)
γ-linolenic acid (CHEBI:28661) has role plant metabolite (CHEBI:76924)
γ-linolenic acid (CHEBI:28661) is a ω−6 fatty acid (CHEBI:36009)
γ-linolenic acid (CHEBI:28661) is a linolenic acid (CHEBI:25048)
γ-linolenic acid (CHEBI:28661) is conjugate acid of γ-linolenate (CHEBI:32391)
Incoming γ-linolenoyl bioconjugate (CHEBI:76187) has functional parent γ-linolenic acid (CHEBI:28661)
γ-linolenoyl-CoA (CHEBI:15508) has functional parent γ-linolenic acid (CHEBI:28661)
γ-linolenoyl-containing glycerolipid (CHEBI:90081) has functional parent γ-linolenic acid (CHEBI:28661)
1-(γ-linolenoyl)-2-oleoyl-sn-glycero-3-phosphate (CHEBI:74936) has functional parent γ-linolenic acid (CHEBI:28661)
1-(γ-linolenoyl)-sn-glycero-3-phosphate (CHEBI:74933) has functional parent γ-linolenic acid (CHEBI:28661)
1-[(6Z,9Z,12Z)-octadecatrienoyl]-2-[(15Z)-tetracosenoyl]-sn-glycero-3-phosphocholine (CHEBI:86422) has functional parent γ-linolenic acid (CHEBI:28661)
1-[(6Z,9Z,12Z)-octadecatrienoyl]-2-[(9Z)-octadecenoyl]-snglycero-3-phosphocholine (CHEBI:86123) has functional parent γ-linolenic acid (CHEBI:28661)
1-[(9Z)-octadecenoyl]-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:86130) has functional parent γ-linolenic acid (CHEBI:28661)
1-hexadecyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:86427) has functional parent γ-linolenic acid (CHEBI:28661)
1-palmitoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:84786) has functional parent γ-linolenic acid (CHEBI:28661)
1-tetracosyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:86451) has functional parent γ-linolenic acid (CHEBI:28661)
10(R)-HPO(6,8,12)TrE (CHEBI:78908) has functional parent γ-linolenic acid (CHEBI:28661)
10-HPO(6,8,12)TrE (CHEBI:84180) has functional parent γ-linolenic acid (CHEBI:28661)
cholesteryl γ-linolenate (CHEBI:88756) has functional parent γ-linolenic acid (CHEBI:28661)
methyl γ-linolenate (CHEBI:144354) has functional parent γ-linolenic acid (CHEBI:28661)
1-octadecanoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:86117) is a γ-linolenic acid (CHEBI:28661)
γ-linolenate (CHEBI:32391) is conjugate base of γ-linolenic acid (CHEBI:28661)
γ-linolenoyl group (CHEBI:32390) is substituent group from γ-linolenic acid (CHEBI:28661)
IUPAC Name
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Synonyms Sources
(6,9,12)-linolenic acid CBN
(6Z,9Z,12Z)-Octadecatrienoic acid KEGG COMPOUND
(Z,Z,Z)-6,9,12-octadecatrienoic acid ChemIDplus
18:3 (n-6) ChEBI
6,9,12-Octadecatrienoic acid KEGG COMPOUND
6-cis,9-cis,12-cis-octadecatrienoic acid ChEBI
all-cis-6,9,12-octadecatrienoic acid ChEBI
C18:3 (n-6) ChEBI
C18:3, n-6,9,12 all-cis ChEBI
cis-Δ6,9,12-octadecatrienoic acid ChEBI
gamma-Linolenic acid KEGG COMPOUND
gamma-Linolenic acid KEGG COMPOUND
γ-Linolensäure ChEBI
gamoleic acid ChEBI
Gamolenic acid KEGG COMPOUND
gamolenic acid ChemIDplus
GLA ChEBI
Octadeca-6,9,12-triensäure ChEBI
Manual Xrefs Databases
1276 DrugCentral
C00001226 KNApSAcK
C06426 KEGG COMPOUND
CPD-8117 MetaCyc
D07213 KEGG DRUG
Gamma-Linolenic_acid Wikipedia
HMDB0003073 HMDB
LMFA01030141 LIPID MAPS
View more database links
Registry Numbers Types Sources
1712253 Reaxys Registry Number Reaxys
506-26-3 CAS Registry Number KEGG COMPOUND
506-26-3 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations
Last Modified
26 July 2019
General Comment
2011-01-21 Found primarily in vegetable oils, it is sold controversially as a dietary supplement for treating problems with inflammation and auto-immune diseases. -- Wikipedia.