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CHEBI:27781 - myristoleic acid

Default Structure
ChEBI IDCHEBI:27781
ChEBI Namemyristoleic acid
Stars
DefinitionA 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.
Secondary ChEBI IDsCHEBI:7058, CHEBI:25454
Last Modified19 February 2020
DownloadsMolfile
FormulaC14H26O2
Net Charge0
Average Mass226.360
Monoisotopic Mass226.19328
SMILESCCCC/C=C\CCCCCCCC(=O)O
InChIInChI=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-
InChIKeyYWWVWXASSLXJHU-WAYWQWQTSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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 ).
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
(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)
O-[(9Z)-tetradecenoyl]-L-carnitine (CHEBI:84647) 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)
1,2-dimyristoleoyl-sn-glycerol (CHEBI:84702) 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  Source
9Z-tetradecenoic acidChEBI
9-Tetradecenoic acidKEGG COMPOUND
(9Z)-Tetradecenoic acidKEGG COMPOUND
cis-9-tetradecenoic acidChEBI
cis-tetradec-9-enoic acidChEBI
cis-Δ9-tetradecenoic acidChEBI
Manual XrefsDatabases
C00001229KNApSAcK
C08322KEGG COMPOUND
HMDB0002000HMDB
LMFA01030051LIPID MAPS
Myristoleic_acidWikipedia
Registry NumbersSources
Reaxys:1724311Reaxys
CAS:544-64-9KEGG COMPOUND
CAS:544-64-9ChemIDplus
Citations