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Chemistry

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Also known as: Minerval, 56472-29-8, 2-hydroxy oleic acid, (z)-2-hydroxyoctadec-9-enoic acid, (rac)-idroxioleic acid, 2-hydroxyoleicacid

Molecular Formula

C₁₈H₃₄O₃

Molecular Weight

298.5 g/mol

InChI Key

JBSOOFITVPOOSY-KTKRTIGZSA-N

FDA UNII

OSV3KVO1BT

Idroxioleic Acid is an orally bioavailable, synthetic analog of the fatty acid oleic acid, with potential antitumor activity. Upon administration,idroxioleic acid 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.

1 2D Structure

2-Hydroxyoleic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 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-

2.1.3 InChI Key

JBSOOFITVPOOSY-KTKRTIGZSA-N

2.1.4 Canonical SMILES

CCCCCCCCC=CCCCCCCC(C(=O)O)O

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

OSV3KVO1BT

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-ohoa Compound

2. 2-hydroxy-9-cis-octadecenoic Acid

3. Minerval

2.3.2 Depositor-Supplied Synonyms

1. Minerval

2. 56472-29-8

3. 2-hydroxy Oleic Acid

4. (z)-2-hydroxyoctadec-9-enoic Acid

5. (rac)-idroxioleic Acid

6. 2-hydroxyoleicacid

7. Cis-2-hydroxy-9-octadecenoic Acid

8. Alpha-hydroxyoleic Acid

9. 2ohoa

10. 9-octadecenoic Acid, 2-hydroxy-, (9z)-

11. 2-hydroxy-9-cis-octadecenoic Acid

12. Osv3kvo1bt

13. 2-hydroxy-9z-hexadecenoic Acid

14. 2-ohoa

15. (9z)-2-hydroxyoctadec-9-enoic Acid

16. 9-octadecenoic Acid, 2-hydroxy-, (z)-

17. Idroxioleic Acid

18. Nfx88

19. Nfx-88

20. Sml0256

21. Oxyolsaure

22. Sml-0256

23. Unii-osv3kvo1bt

24. Schembl378126

25. Idroxioleic Acid [inn]

26. 2-hydroxy-9z-octadecenoic Acid

27. Cis-2-hydroxy9-octadecenoic Acid

28. Dtxsid00430863

29. Chebi:143096

30. Jbsoofitvpoosy-ktkrtigzsa-n

31. Glxc-01960

32. 2-hydroxy-9(z)-octadecenoic Acid

33. Lmfa01050540

34. 2ohoa, >=98% (hplc)

35. 2-hydroxyoleic Acid [who-dd]

36. Akos040742138

37. 9-octadecenoicacid,2-hydroxy-,(9z)-

38. Bp-29870

39. Ts-07995

40. Db-228095

41. Hy-129467

42. Cs-0105697

43. G13409

44. Rac-(2r,9z)-2-hydroxyoctadec-9-enoic Acid

45. Q28816084

46. Z2312477358

47. (9z)-2-hydroxy-9-octadecenoic Acid; 2-hydroxyoleic Acid

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₃₄O₃
Molecular Weight	298.5 g/mol
XLogP3	6.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	15
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	57.5
Heavy Atom Count	21
Formal Charge	0
Complexity	261
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1