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
Supplier Information ChemicalBook:CB9666441, ChemicalBook:CB2112323, eMolecules:524832, ZINC000003802189
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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
Last Modified
31 May 2023