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α-linolenic acid (CHEBI:27432)

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ChEBI Name α-linolenic acid
ChEBI ID CHEBI:27432
ChEBI ASCII Name alpha-linolenic acid
Definition A linolenic acid with cis-double bonds at positions 9, 12 and 15. Shown to have an antithrombotic effect.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43891, CHEBI:22462, CHEBI:10298
Supplier Information
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Formula Source
C18H30O2 KEGG COMPOUND
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/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-
InChIKey
DTOSIQBPPRVQHS-PDBXOOCHSA-N
SMILES
CC\C=C/C\C=C/C\C=C/CCCCCCCC(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): micronutrient

marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
(via omega-3 fatty acid )
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via omega-3 fatty acid )
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via omega-3 fatty acid )
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
(via omega-3 fatty acid )
Application(s): nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing α-linolenic acid (CHEBI:27432) has role micronutrient (CHEBI:27027)
α-linolenic acid (CHEBI:27432) has role nutraceutical (CHEBI:50733)
α-linolenic acid (CHEBI:27432) is a ω−3 fatty acid (CHEBI:25681)
α-linolenic acid (CHEBI:27432) is a linolenic acid (CHEBI:25048)
α-linolenic acid (CHEBI:27432) is conjugate acid of α-linolenate (CHEBI:32387)
α-linolenic acid (CHEBI:27432) is conjugate acid of (9Z,12Z,15Z)-octadeca-9,12,15-trienoate (CHEBI:528881)
Incoming α-linolenoyl bioconjugate (CHEBI:76184) has functional parent α-linolenic acid (CHEBI:27432)
α-linolenoyl-CoA (CHEBI:51985) has functional parent α-linolenic acid (CHEBI:27432)
(R)-2-hydroperoxy-α-linolenic acid (CHEBI:76236) has functional parent α-linolenic acid (CHEBI:27432)
(R)-2-hydroxy-α-linolenic acid (CHEBI:76234) has functional parent α-linolenic acid (CHEBI:27432)
1,2,3-trilinolenoylglycerol (CHEBI:75845) has functional parent α-linolenic acid (CHEBI:27432)
1,3-dilinolenoylglycerol (CHEBI:75852) has functional parent α-linolenic acid (CHEBI:27432)
1-α-linolenoyl-2-oleoylglycerol (CHEBI:75609) has functional parent α-linolenic acid (CHEBI:27432)
1-α-linolenoylglycerol (CHEBI:75610) has functional parent α-linolenic acid (CHEBI:27432)
1-linolenoyl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:74833) has functional parent α-linolenic acid (CHEBI:27432)
1-linolenoyl-sn-glycero-3-phosphate (CHEBI:74831) has functional parent α-linolenic acid (CHEBI:27432)
1-linolenyl-2-linoleyl-PAP (CHEBI:53755) has functional parent α-linolenic acid (CHEBI:27432)
1-oleoyl-2-(α-linolenoyl)-sn-glycerol (CHEBI:75475) has functional parent α-linolenic acid (CHEBI:27432)
1-oleoyl-2-linolenoyl-PAP (CHEBI:53754) has functional parent α-linolenic acid (CHEBI:27432)
1-stearoyl-2-(α-linolenoyl)-sn-glycero-3-phosphocholine (CHEBI:78022) has functional parent α-linolenic acid (CHEBI:27432)
2,3-dilinolenoyl-sn-glycerol (CHEBI:75855) has functional parent α-linolenic acid (CHEBI:27432)
2-α-linolenoylglycerol (CHEBI:75474) has functional parent α-linolenic acid (CHEBI:27432)
linolenic acid anilide (CHEBI:53751) has functional parent α-linolenic acid (CHEBI:27432)
α-linolenate (CHEBI:32387) is conjugate base of α-linolenic acid (CHEBI:27432)
(9Z,12Z,15Z)-octadeca-9,12,15-trienoate (CHEBI:528881) is conjugate base of α-linolenic acid (CHEBI:27432)
α-linolenoyl group (CHEBI:32388) is substituent group from α-linolenic acid (CHEBI:27432)
IUPAC Name
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Synonyms Sources
(9,12,15)-linolenic acid CBN
(9Z,12Z,15Z)-Octadecatrienoic acid KEGG COMPOUND
(Z,Z,Z)-9,12,15-octadecatrienoic acid NIST Chemistry WebBook
9,12,15-Octadecatrienoic acid KEGG COMPOUND
9-cis,12-cis,15-cis-octadecatrienoic acid ChemIDplus
ALA ChEBI
all-cis-9,12,15-octadecatrienoic acid NIST Chemistry WebBook
alpha-Linolenic acid KEGG COMPOUND
ALPHA-LINOLENIC ACID PDBeChem
α-linolenic acid NIST Chemistry WebBook
alpha-Linolenic acid KEGG COMPOUND
cis,cis,cis-9,12,15-octadecatrienoic acid NIST Chemistry WebBook
cis9,12,15-octadecatrienoic acid ChemIDplus
linolenic acid ChEBI
Database Links Databases
Alpha-Linolenic_acid Wikipedia
C00007247 KNApSAcK
C06427 KEGG COMPOUND
DB00132 DrugBank
HMDB01388 HMDB
LINOLENIC_ACID MetaCyc
LMFA01030152 LIPID MAPS
LNL PDBeChem
View more database links
Registry Numbers Types Sources
1727693 Reaxys Registry Number Reaxys
1727693 Beilstein Registry Number Beilstein
463-40-1 CAS Registry Number KEGG COMPOUND
463-40-1 CAS Registry Number ChemIDplus
463-40-1 CAS Registry Number NIST Chemistry WebBook
57558 Gmelin Registry Number Gmelin
Citations Waiting for Citations Types Sources
10232625 PubMed citation CiteXplore
11304127 PubMed citation CiteXplore
19269799 PubMed citation CiteXplore
24320056 PubMed citation CiteXplore
24639012 PubMed citation CiteXplore
24855655 PubMed citation CiteXplore
Last Modified
28 July 2014

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