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
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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
1712253 Beilstein Registry Number Beilstein
506-26-3 CAS Registry Number KEGG COMPOUND
506-26-3 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
11385052 PubMed citation Europe PMC
24435467 PubMed citation Europe PMC
9732298 PubMed citation Europe PMC
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.