2-hydroxyoleic acid (CHEBI:143096)

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ChEBI Name	2-hydroxyoleic acid

ChEBI ID	CHEBI:143096

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C18H34O3

Net Charge

Average Mass

298.461

Monoisotopic Mass

298.25079

InChI

InChI=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-

InChIKey

JBSOOFITVPOOSY-KTKRTIGZSA-N

SMILES

C(\CCCCCCC(C(=O)O)O)=C\CCCCCCCC

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.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. antihypertensive agent Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.

ChEBI Ontology
Outgoing	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	2-hydroxyoleate (CHEBI:142986) is conjugate base of 2-hydroxyoleic acid (CHEBI:143096)

IUPAC Name

(9Z)-2-hydroxyoctadec-9-enoic acid

Synonyms	Sources
(Z)-2-hydroxyoctadec-9-enoic acid	ChEBI
2-hydroxy-9-cis-octadecenoic acid	ChemIDplus
2-hydroxy-9Z-octadecenoic acid	ChEBI
2-OHOA	ChEBI
2OHOA	ChEBI
α-hydroxyoleic acid	ChemIDplus
cis-2-hydroxy-9-octadecenoic acid	ChEBI

Brand Name	Source
Minerval	ChemIDplus

Registry Number	Type	Source
56472-29-8	CAS Registry Number	ChemIDplus

Last Modified

14 February 2019