Idroxioleic Acid

U.S. Department of Health & Human Services Divider Arrow

National Institutes of Health Divider Arrow

NCATS

Investigational

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H34O3
Molecular Weight	298.4608
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure of Idroxioleic Acid

Structure Search

SMILES

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

InChI

InChIKey=JBSOOFITVPOOSY-KTKRTIGZSA-N

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-

HIDE SMILES / InChI

Molecular Formula	C18H34O3
Molecular Weight	298.4608
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	1
Optical Activity	( + / - )

Approval Year

Targets

Targets

Primary Target	Pharmacology	Condition	Potency
sphingomyelin biosynthetic process 2 Target ID: GO:0006686 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22106271	Activator 1447

PubMed

PubMed

Title	Date	PubMed
The repression of E2F-1 is critical for the activity of Minerval against cancer.	2005-10	16027227

Patents

Patents

Substance Class	Chemical Created by `admin` on `Tue Apr 01 16:40:11 GMT 2025` Edited by `admin` on `Tue Apr 01 16:40:11 GMT 2025`
Record UNII	OSV3KVO1BT
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

2-OHOA

Preferred Name

English

Idroxioleic Acid

Official Name

English

2-HYDROXYOLEIC ACID

Systematic Name

English

idroxioleic acid [INN]

Common Name

English

NFX88

Code

English

9-Octadecenoic acid, 2-hydroxy-, (9Z)-

Systematic Name

English

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

Systematic Name

English

NFX-88

Code

English

IDROXIOLEIC ACID [USAN]

Common Name

English

ALPHA-HYDROXYOLEIC ACID

Systematic Name

English

SML-0256

Code

English

CIS-2-HYDROXY-9-OCTADECENOIC ACID

Systematic Name

English

2-hydroxyoleic acid [WHO-DD]

Common Name

English

MINERVAL

Common Name

English

SML0256

Code

English

RAC-(2R,9Z)-2-HYDROXYOCTADEC-9-ENOIC ACID

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

844021

Created by admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025

EU-Orphan Drug

EU/3/11/916

Created by admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025

NCI_THESAURUS

C274

Created by admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025

Code System Code Type Description

EPA CompTox

DTXSID00430863

Created by admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025

PRIMARY

PUBCHEM

9796304

Created by admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025

PRIMARY

INN

11607

Created by admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025

PRIMARY

INN

NCI_THESAURUS

C105401

Created by admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025

PRIMARY

NCIT

CAS

56472-29-8

Created by admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025

PRIMARY

SMS_ID

100000181927

Created by admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025

PRIMARY

EVMPD

SUB195753

Created by admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025

PRIMARY

USAN

MN-165

Created by admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025

PRIMARY

CHEBI

143096

Created by admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025

PRIMARY

MANUFACTURER PRODUCT INFORMATION

2-HYDROXYOLEIC ACID

Created by admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025

PRIMARY

Biochem/physiol Actions: 2OHOA induces cell cycle arrest and apoptosis in several cancer cell lines, including glioma, leukemia, breast and colon cancer lines. 2OHOA increases sphingomyelin (SM) levels in the membranes of tumor cells, which typically display decreased SM membrane content, and remodeled membranes, compared with normal cells. The compound has no effect on SM levels in non-cancer cells.

FDA UNII

OSV3KVO1BT

Created by admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025

PRIMARY

Related Record Type Details


					RM48RG3YA7

PHOSPHATIDYLCHOLINE:CERAMIDE CHOLINEPHOSPHOTRANSFERASE 1

TARGET -> ACTIVATOR

Amount:


					Q0O588YY4Z

Idroxioleate Sodium

SALT/SOLVATE -> PARENT

Amount:

Related Record Type Details


					OSV3KVO1BT

Idroxioleic Acid

ACTIVE MOIETY

Comments:

2-hydroxyoleic acid An orally bioavailable, synthetic analog of the fatty acid oleic acid, with potential antitumor activity. Upon administration, 2-hydroxyoleic acid (2OHOA) activates sphingomyelin synthase (SMS), thereby increasing the concentration of sphingomyelin (SM) and diacylglycerol (DAG) in the tumor cell membrane and decreasing membrane levels of phosphatidylethanolamine (PE) and phosphatidylcholine (PC). This restores the normal, healthy levels and ratios of membrane lipids. By restoring normal membrane lipid structure and composition, this agent inhibits membrane-protein associated signaling and the aberrant activity of signaling pathways in certain tumor cells, including the Ras/MAPK and PI3K/AKt pathways. This inhibits tumor cell proliferation, induces tumor cell differentiation, and eventually can cause cell death. Check for active clinical trials using this agent. (NCI Thesaurus)

Amount: