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Enoxolone

Synopsis

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Chemistry

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Also known as: Uralenic acid, 3-hydroxy-11-oxoolean-12-en-29-oic acid, Glycyrrhetin, Biosone, 3-glycyrrhetinic acid, .alpha.-glycyrrhetinic acid

Molecular Formula

C₃₀H₄₆O₄

Molecular Weight

470.7 g/mol

InChI Key

MPDGHEJMBKOTSU-UHFFFAOYSA-N

An oleanolic acid from GLYCYRRHIZA that has some antiallergic, antibacterial, and antiviral properties. It is used topically for allergic or infectious skin inflammation and orally for its aldosterone effects in electrolyte regulation.

1 2D Structure

Enoxolone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)

2.1.3 InChI Key

MPDGHEJMBKOTSU-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1(C2CCC3(C(C2(CCC1O)C)C(=O)C=C4C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 12, Po

2. Acid, Glycyrrhetic

3. Acid, Glycyrrhetinic

4. Acid, Rhetinic

5. Acid, Uralenic

6. Arthrodont

7. Enoxolone

8. Glyciram

9. Glycyram

10. Glycyrrhetic Acid

11. Jintan

12. Po 12

13. Rhetinic Acid

14. Uralenic Acid

2.2.2 Depositor-Supplied Synonyms

1. Uralenic Acid

2. 3-hydroxy-11-oxoolean-12-en-29-oic Acid

3. Glycyrrhetin

4. Biosone

5. 3-glycyrrhetinic Acid

6. .alpha.-glycyrrhetinic Acid

7. 18.beta.-glycyrrhetic Acid

8. 18.beta.-glycyrrhtinic Acid

9. 18.beta.-glycyrrhetinic Acid

10. Nsc35347

11. Nsc35350

12. 1449-05-4

13. Arthrodont

14. 3.beta.-hydroxy-11-oxoolean-12-en-30-oic Acid

15. Olean-12-en-30-oic Acid, 3.beta.-hydroxy-11-oxo-

16. Nsc 35347

17. 18a-glycyrrhetinic Acid

18. Nsc-35350

19. Glyccyrhetic Acid

20. Ncgc00181115-01

21. 10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1h-picene-2-carboxylic Acid

22. 18-glycyrrhetinic Acid

23. .beta.-glycyrrhetic Acid

24. .beta.-glycyrrhetinic Acid

25. Schembl25465

26. 18-.beta.-glycrrhetinic Acid

27. 18.alpha.-glycyrrhetinic Acid

28. 18-.beta.-glycyrrhetinic Acid

29. Chembl1863561

30. Glycyrrhetinic Acid, 18 Alpha-

31. Dtxsid50859383

32. Bbl009942

33. Glycyrrhetinic Acid,18 Alpha

34. Mfcd00066716

35. Olean-12-en-29-oic Acid, 3-hydroxy-11-oxo-, (3.beta.,20.beta.)-

36. Stk801355

37. Akos005612983

38. P.o. 12

39. Nci60_003170

40. Vs-02260

41. Db-042758

42. Ft-0633550

43. N1795

44. Olean-12-en-29-oic Acid, (3.beta.,20.beta.)-

45. 3.beta.-hydroxy-11-oxo-18.alpha.-olean-12-en-30-oic Acid

46. Olean-12-en-29-oic Acid, (3.beta.,18.alpha.,20.beta.)-

47. (3.beta.,20.beta.)-3-hydroxy-11-oxoolean-12-en-29-oic Acid

48. 18.alpha.-olean-12-en-30-oic Acid, 3.beta.-hydroxy-11-oxo-

49. 3-hydroxy-11-oxoolean-12-en-29-oic Acid, (3.beta.,20.beta.)- #

50. Wln: L F6 E6 B666 Cv Dutj A1 Hvq H1 K1 N1 O1 S1 S1 Tq -.alpha.

51. Wln: L F6 E6 B666 Cv Dutj A1 Hvq H1 K1 N1 O1 S1 S1 Tq -beta

52. 10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic Acid

53. 1970133-69-7

2.3 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₃₀H₄₆O₄
Molecular Weight	470.7 g/mol
XLogP3	6.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	1
Exact Mass	470.33960994 g/mol
Monoisotopic Mass	470.33960994 g/mol
Topological Polar Surface Area	74.6 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	965
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	9
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1