IDROXIOLEIC ACID

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

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	MOL RATIO 1 MOL RATIO (average)

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

Approval Year

Substance Class	Chemical
Record UNII	OSV3KVO1BT
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

IDROXIOLEIC ACID

Official Name

English

2-OHOA

Common Name

English

2-HYDROXYOLEIC ACID

Systematic Name

English

idroxioleic acid [INN]

Common Name

English

NFX88

Code

English

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Classification Tree

Code System

Code

Designated

FDA ORPHAN DRUG

844021

Positive

EU-Orphan Drug

EU/3/11/916

Pharmacologic Substance

NCI_THESAURUS

C274

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Code System

Code

Type

Description

EPA CompTox

DTXSID00430863

PRIMARY

PUBCHEM

9796304

PRIMARY

INN

11607

PRIMARY

INN

NCI_THESAURUS

C105401

PRIMARY

NCIT

CAS

56472-29-8

PRIMARY

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PHOSPHATIDYLCHOLINE:CERAMIDE CHOLINEPHOSPHOTRANSFERASE 1

TARGET -> ACTIVATOR

Amount:


					Q0O588YY4Z

SODIUM IDROXIOLEATE

SALT/SOLVATE -> PARENT

Amount:

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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:


					OSV3KVO1BT

IDROXIOLEIC ACID

ACTIVE MOIETY

Comments:

2OHOA is an orally administered bio-active lipid that specifically activates SMS1, a key enzyme that catalyses the reversible conversion of PC, PE and Cer into SM and DAG at cell-membrane level. Membrane lipid composition and organization is known to be significantly altered in cancer cells and it has been observed that these changes are enabling increased recruitment to the cell membrane of central proliferation signalling proteins, such as K-Ras. Over-activation of Ras signalling is known to play a critical role in key proliferation pathways including Ras/MAPK, Pi3K/AKT/mTOR or PKC/Cyclin CDK. Activation of SMS1 in cancer cells induces marked increases in its main product (SM), accompanied by reductions in the levels of its substrates (PC and PE), causing normalization of membrane levels of PE, PC and SM. By contrast, Minerval does not significantly alter membrane lipid composition in non-tumour cells, because the enzyme product (SM) is found already in high levels and its substrates are limiting.

Amount:

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