CHEBI:27432 - α-linolenic acid

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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:10298, CHEBI:22462
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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/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
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606) Found in blood serum (BTO:0000133). See: MetaboLights Study
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
Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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 )
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 )
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 via ChEBI Ontology
ChEBI Ontology
Outgoing α-linolenic acid (CHEBI:27432) has role micronutrient (CHEBI:27027)
α-linolenic acid (CHEBI:27432) has role mouse metabolite (CHEBI:75771)
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-sn-glycero-3-phosphocholine (CHEBI:140445) has functional parent α-linolenic acid (CHEBI:27432)
α-linolenoyl-CoA (CHEBI:51985) has functional parent α-linolenic acid (CHEBI:27432)
α-linolenoyl-containing glycerolipid (CHEBI:90078) has functional parent α-linolenic acid (CHEBI:27432)
(9Z,11R,12Z,15Z)-11-hydroperoxyoctadecatrienoic acid (CHEBI:133988) has functional parent α-linolenic acid (CHEBI:27432)
(9Z,11S,12Z,15Z)-11-hydroperoxyoctadecatrienoic acid (CHEBI:136686) has functional parent α-linolenic acid (CHEBI:27432)
(9Z,12Z,15Z)-octadecatrienamide (CHEBI:142684) 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)
1,2-di-(α-linolenoyl)-3-[α-D-galactosyl-(1→6)-β-D-galactosyl]-sn-glycerol (CHEBI:136795) has functional parent α-linolenic acid (CHEBI:27432)
1,2-di-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:86161) 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-[(11Z)-icosenoyl]-sn-glycerol (CHEBI:89240) has functional parent α-linolenic acid (CHEBI:27432)
1-α-linolenoyl-2-[(11Z,14Z)-icosadienoyl]-sn-glycerol (CHEBI:89239) has functional parent α-linolenic acid (CHEBI:27432)
1-α-linolenoyl-2-[(5Z,8Z,11Z)-icosatrienoyl]-sn-glycerol (CHEBI:89238) has functional parent α-linolenic acid (CHEBI:27432)
1-α-linolenoyl-2-[(8Z,11Z,14Z)-icosatrienoyl]-sn-glycerol (CHEBI:89237) has functional parent α-linolenic acid (CHEBI:27432)
1-α-linolenoyl-2-hexadecanoylphosphatidylglycerol (CHEBI:136802) has functional parent α-linolenic acid (CHEBI:27432)
1-α-linolenoyl-2-icosanoyl-sn-glycerol (CHEBI:89241) 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-(9Z,12Z,15Z)-octadecatrienoyl-2-(7Z,10Z,13Z)-hexadecatrienoyl-3-(β-D-galactosyl)-sn-glycerol (CHEBI:90552) has functional parent α-linolenic acid (CHEBI:27432)
1-(9Z,12Z,15Z-octadecatrienoyl)-2-hexadecanoyl-3-[α-D-galactosyl-(1→6)-β-D-galactosyl]-sn-glycerol (CHEBI:136797) has functional parent α-linolenic acid (CHEBI:27432)
1-[(9Z)-octadecenoyl]-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:86133) has functional parent α-linolenic acid (CHEBI:27432)
1-[(9Z,12Z,15Z)-octadecatrienoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86127) has functional parent α-linolenic acid (CHEBI:27432)
1-heptadecanoyl-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:131660) 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-palmitoyl-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:84789) 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)
1-tetradecanoyl-2-[(9Z,12Z,15Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:86095) 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)
N-(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl-(2S)-hydroxyglycine (CHEBI:142735) has functional parent α-linolenic acid (CHEBI:27432)
N-(9Z,12Z,15Z)-octadecatrienoylglycine (CHEBI:142736) has functional parent α-linolenic acid (CHEBI:27432)
cholesteryl linolenate (CHEBI:84341) has functional parent α-linolenic acid (CHEBI:27432)
ethyl linolenate (CHEBI:84851) has functional parent α-linolenic acid (CHEBI:27432)
linolenic acid anilide (CHEBI:53751) has functional parent α-linolenic acid (CHEBI:27432)
methyl linolenate (CHEBI:133634) has functional parent α-linolenic acid (CHEBI:27432)
soybean oil (CHEBI:166975) has part 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
alpha-Linolenic acid KEGG COMPOUND
α-linolenic acid NIST Chemistry WebBook
cis,cis,cis-9,12,15-octadecatrienoic acid NIST Chemistry WebBook
cis-Δ9,12,15-octadecatrienoic acid ChemIDplus
linolenic acid ChEBI
Manual Xrefs Databases
4618 DrugCentral
Alpha-Linolenic_acid Wikipedia
C00007247 KNApSAcK
C06427 KEGG COMPOUND
DB00132 DrugBank
HMDB0001388 HMDB
LINOLENIC_ACID MetaCyc
LMFA01030152 LIPID MAPS
LNL PDBeChem
View more database links
Registry Numbers Types Sources
1727693 Reaxys Registry Number Reaxys
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 Europe PMC
11304127 PubMed citation Europe PMC
19269799 PubMed citation Europe PMC
24320056 PubMed citation Europe PMC
24639012 PubMed citation Europe PMC
24855655 PubMed citation Europe PMC
Last Modified
31 May 2023