EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:143096 - 2-hydroxyoleic acid

ChEBI IDCHEBI:143096
ChEBI Name2-hydroxyoleic acid
Stars
DefinitionA 2-hydroxy fatty acid that is oleic acid which carries a hydroxy group at position 2. It is an orally bioavailable synthetic hydroxylated fatty acid which modulates the lipid content of cancer cell membranes and induces cell cycle arrest and apoptosis in several cancer cell lines.
Last Modified14 February 2019
SubmitterAdnan
DownloadsMolfile
FormulaC18H34O3
Net Charge0
Average Mass298.467
Monoisotopic Mass298.25079
SMILESCCCCCCCC/C=C\CCCCCCC(O)C(=O)O
InChIInChI=1S/C18H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(19)18(20)21/h9-10,17,19H,2-8,11-16H2,1H3,(H,20,21)/b10-9-
InChIKeyJBSOOFITVPOOSY-KTKRTIGZSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Applications:
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
2-hydroxyoleic acid (CHEBI:143096) has functional parent oleic acid (CHEBI:16196)
2-hydroxyoleic acid (CHEBI:143096) has role antihypertensive agent (CHEBI:35674)
2-hydroxyoleic acid (CHEBI:143096) has role antineoplastic agent (CHEBI:35610)
2-hydroxyoleic acid (CHEBI:143096) has role apoptosis inducer (CHEBI:68495)
2-hydroxyoleic acid (CHEBI:143096) is a 2-hydroxy fatty acid (CHEBI:10283)
2-hydroxyoleic acid (CHEBI:143096) is a hydroxy monounsaturated fatty acid (CHEBI:131869)
2-hydroxyoleic acid (CHEBI:143096) is a long-chain fatty acid (CHEBI:15904)
2-hydroxyoleic acid (CHEBI:143096) is conjugate acid of 2-hydroxyoleate (CHEBI:142986)
Incoming Relation(s)
2-hydroxyoleate (CHEBI:142986) is conjugate base of 2-hydroxyoleic acid (CHEBI:143096)
IUPAC Name 
(9Z)-2-hydroxyoctadec-9-enoic acid
Synonyms  Source
2-hydroxy-9Z-octadecenoic acidChEBI
(Z)-2-hydroxyoctadec-9-enoic acidChEBI
2-hydroxy-9-cis-octadecenoic acidChemIDplus
α-hydroxyoleic acidChemIDplus
2OHOAChEBI
cis-2-hydroxy-9-octadecenoic acidChEBI
Brand Name  Source
MinervalChemIDplus
Manual XrefsDatabases
LMFA01050540LIPID MAPS
Registry NumbersSources
CAS:56472-29-8ChemIDplus
Citations