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CHEBI:28661 - γ-linolenic acid

ChEBI IDCHEBI:28661
ChEBI Nameγ-linolenic acid
Stars
ASCII Namegamma-linolenic acid
DefinitionA C18, ω-6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12.
Secondary ChEBI IDsCHEBI:10573, CHEBI:24197
Last Modified26 July 2019
DownloadsMolfile
FormulaC18H30O2
Net Charge0
Average Mass278.436
Monoisotopic Mass278.22458
SMILESCCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O
InChIInChI=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-
InChIKeyVZCCETWTMQHEPK-QNEBEIHSSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Chemical Roles:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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.
ChEBI Ontology
Outgoing Relation(s)
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 linolenic acid (CHEBI:25048)
γ-linolenic acid (CHEBI:28661) is a ω−6 fatty acid (CHEBI:36009)
γ-linolenic acid (CHEBI:28661) is conjugate acid of γ-linolenate (CHEBI:32391)
Incoming Relation(s)
1-(γ-linolenoyl)-sn-glycero-3-phosphate (CHEBI:74933) 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-[(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-HPO(6,8,12)TrE (CHEBI:84180) 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)
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)
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-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  Source
gamma-Linolenic acidKEGG COMPOUND
6,9,12-Octadecatrienoic acidKEGG COMPOUND
gamolenic acidChemIDplus
(6,9,12)-linolenic acidIUBMB
(Z,Z,Z)-6,9,12-octadecatrienoic acidChemIDplus
all-cis-6,9,12-octadecatrienoic acidChEBI
Manual XrefsDatabases
C06426KEGG COMPOUND
C06426KEGG COMPOUND
LMFA01030141LIPID MAPS
CPD-8117MetaCyc
Gamma-Linolenic_acidWikipedia
HMDB0003073HMDB
C00001226KNApSAcK
D07213KEGG DRUG
1276DrugCentral
Registry NumbersSources
Reaxys:1712253Reaxys
CAS:506-26-3KEGG COMPOUND
CAS:506-26-3NIST Chemistry WebBook
Citations