CHEBI:27781 - myristoleic acid

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ChEBI Name myristoleic acid
ChEBI ID CHEBI:27781
Definition A tetradecenoic acid in which the double bond is at the 9-10 position and has Z configuration. Myristoleic acid has been isolated from Serenoa repens and has cytotoxic and apoptosis-inducing effects.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:7058, CHEBI:25454
Supplier Information No supplier information found for this compound.
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Formula C14H26O2
Net Charge 0
Average Mass 226.35500
Monoisotopic Mass 226.19328
InChI InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-
InChIKey YWWVWXASSLXJHU-WAYWQWQTSA-N
SMILES CCCC\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): apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
EC 3.1.1.1 (carboxylesterase) inhibitor
Any EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that inhibits the action of carboxylesterase (EC 3.1.1.1 ).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing myristoleic acid (CHEBI:27781) has role apoptosis inducer (CHEBI:68495)
myristoleic acid (CHEBI:27781) has role EC 3.1.1.1 (carboxylesterase) inhibitor (CHEBI:78444)
myristoleic acid (CHEBI:27781) has role plant metabolite (CHEBI:76924)
myristoleic acid (CHEBI:27781) is a long-chain fatty acid (CHEBI:15904)
myristoleic acid (CHEBI:27781) is a tetradecenoic acid (CHEBI:36004)
myristoleic acid (CHEBI:27781) is conjugate acid of myristoleate (CHEBI:32370)
Incoming (9Z)-myristoleoyl-CoA (CHEBI:65087) has functional parent myristoleic acid (CHEBI:27781)
(9Z)-myristoleoyl-CoA(4−) (CHEBI:65060) has functional parent myristoleic acid (CHEBI:27781)
1,2-dimyristoleoyl-sn-glycerol (CHEBI:84702) has functional parent myristoleic acid (CHEBI:27781)
1-[(9Z)-hexadecenoyl]-2-[(9Z)-tetradecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86415) has functional parent myristoleic acid (CHEBI:27781)
1-[(9Z)-hexadecenyl]--[(9Z)-tetradecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86423) has functional parent myristoleic acid (CHEBI:27781)
1-[(9Z)-tetradecenoyl]-2-[(5Z,8Z,11Z,14Z)-icosatetraenoyl]-sn-glycerol (CHEBI:86977) has functional parent myristoleic acid (CHEBI:27781)
O-[(9Z)-tetradecenoyl]-L-carnitine (CHEBI:84647) has functional parent myristoleic acid (CHEBI:27781)
myristoleamide (CHEBI:146161) has functional parent myristoleic acid (CHEBI:27781)
myristoleate (CHEBI:32370) is conjugate base of myristoleic acid (CHEBI:27781)
myristoleoyl group (CHEBI:32371) is substituent group from myristoleic acid (CHEBI:27781)
IUPAC Name
(9Z)-tetradec-9-enoic acid
Synonyms Sources
(9Z)-Tetradecenoic acid KEGG COMPOUND
(Z)-Tetradec-9-enoic acid KEGG COMPOUND
9-Tetradecenoic acid KEGG COMPOUND
9Z-tetradecenoic acid ChEBI
cis-9-tetradecenoic acid ChEBI
cis-Δ9-tetradecenoic acid ChEBI
cis-tetradec-9-enoic acid ChEBI
Myristoleic acid KEGG COMPOUND
Myristoleic acid KEGG COMPOUND
Manual Xrefs Databases
C00001229 KNApSAcK
C08322 KEGG COMPOUND
HMDB0002000 HMDB
LMFA01030051 LIPID MAPS
Myristoleic_acid Wikipedia
View more database links
Registry Numbers Types Sources
1724311 Reaxys Registry Number Reaxys
544-64-9 CAS Registry Number ChemIDplus
Citations Types Sources
11304730 PubMed citation Europe PMC
11380153 PubMed citation Europe PMC
19761868 PubMed citation Europe PMC
Last Modified
19 February 2020