CHEBI:28661 - γ-linolenic acid

Main ChEBI Ontology Automatic Xrefs
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
Save molfile Download Molfile
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C18H30O2
Net Charge 0
Average Mass 278.42960
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
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): 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.
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 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)
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-palmitoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:84786) 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)
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
cis6,9,12-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
Database Links Databases
C00001226 KNApSAcK
C06426 KEGG COMPOUND
CPD-8117 MetaCyc
D07213 KEGG DRUG
Gamma-Linolenic_acid Wikipedia
HMDB03073 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 CiteXplore
24435467 PubMed citation CiteXplore
9732298 PubMed citation CiteXplore
Last Modified
13 February 2015
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.