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Chemistry

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Also known as: Metribolone, 965-93-5, R1881, 17alpha-methyltrienolone, Metribolona, Metribolonum
Molecular Formula
C19H24O2
Molecular Weight
284.4  g/mol
InChI Key
CCCIJQPRIXGQOE-XWSJACJDSA-N
FDA UNII
2C323EGI97

Metribolone
A synthetic non-aromatizable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.
1 2D Structure

Metribolone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(8S,13S,14S,17S)-17-hydroxy-13,17-dimethyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
2.1.2 InChI
InChI=1S/C19H24O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h7,9,11,16-17,21H,3-6,8,10H2,1-2H3/t16-,17+,18+,19+/m1/s1
2.1.3 InChI Key
CCCIJQPRIXGQOE-XWSJACJDSA-N
2.1.4 Canonical SMILES
CC1(CCC2C1(C=CC3=C4CCC(=O)C=C4CCC23)C)O
2.1.5 Isomeric SMILES
C[C@@]1(CC[C@@H]2[C@@]1(C=CC3=C4CCC(=O)C=C4CC[C@@H]23)C)O
2.2 Other Identifiers
2.2.1 UNII
2C323EGI97
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 17 Beta-hydroxy-17 Alpha-methylestra-4,9,11-trien-3-one

2. Metribolone

3. R 1881

4. R-1881

5. R1881

6. Ru 1881

7. Ru-1881

8. Ru1881

2.3.2 Depositor-Supplied Synonyms

1. Metribolone

2. 965-93-5

3. R1881

4. 17alpha-methyltrienolone

5. Metribolona

6. Metribolonum

7. R 1881

8. Ru 1881

9. 17-beta-hydroxy-17-methylestra-4,9,11-trien-3-one

10. R-1881

11. (17beta)-17-hydroxy-17-methylestra-4,9,11-trien-3-one

12. 17beta-hydroxy-17-methylestra-4,9,11-trien-3-one

13. Nsc-92858

14. R1881 (synthetic Androgen)

15. Chebi:379896

16. 2c323egi97

17. Estra-4,9,11-trien-3-one, 17-hydroxy-17-methyl-, (17b)-

18. Estra-4,9,11-trien-3-one, 17-hydroxy-17-methyl-, (17beta)-

19. 17-methyloestra-4,9,11-trien-3-one,17beta-ol

20. (8s,13s,14s,17s)-17-hydroxy-13,17-dimethyl-1,2,6,7,8,13,14,15,16,17-decahydro-3h-cyclopenta[a]phenanthren-3-one

21. (8s,13s,14s,17s)-17-hydroxy-13,17-dimethyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one

22. Ru-1881

23. [3h]methyltrienolone

24. Mls002695156

25. Metribolone [inn:dcf]

26. Metribolonum [inn-latin]

27. Metribolona [inn-spanish]

28. Unii-2c323egi97

29. Methyl Trienolone

30. 1xow

31. Nsc 92858

32. 1e3g

33. 2ao6

34. [3h]r1881

35. Metribolone [inn]

36. [3h]-r1881

37. 17.alpha.-methyltrienolone

38. Metribolone [mart.]

39. 17-.alpha.-methyltrienolone

40. Methyltrienolone [mi]

41. Metribolone [who-dd]

42. Schembl114862

43. Chembl166444

44. Gtpl2857

45. Gtpl3457

46. Dtxsid8034162

47. Nsc92858

48. Zinc3814420

49. Bdbm50367916

50. Akos015840270

51. Db02998

52. Ac-32028

53. R1881, >=98% (hplc)

54. 965m935

55. A845615

56. Q3333717

57. 17-.beta.-hydroxy-17-methylestra-4,11-trien-3-one

58. 17alpha-methyl-3-oxo-4,9,11-estratrien-17beta-ol

59. 17alpha-methyl-4,9,11,estratrien-17beta-ol-3-one

60. 3-oxo-17beta-hydroxy-17-methylestra-4,9,11-triene

61. 17alpha-methyl-17beta-hydroxyestr-4,9,11-trien-3-one

62. 17alpha-methyl-17beta-hydroxyestra-4,9,11-trien-3-one

63. Estra-4,11-trien-3-one, 17.beta.-hydroxy-17-methyl-

64. Estra-4,9,11-trien-3-one, 17beta-hydroxy-17-methyl-

65. 17alpha-methyl-17beta-hydroxy-estra-4,9,11-trien-3-one

66. 3-oxo-17beta-hydroxy-17alpha-methylestra-4,9,11-triene

67. (17beta)-17-hydroxy-17-methyl-estra-4,9,11-triene-3-one

68. 17-beta-hydroxy-17-methylestra-4,9,11-trien-3-one (9ci)

69. 17.beta.-hydroxy-17-methylestra-4,9,11-trien-3-one

70. 17alpha-methyl-17beta-hydroxyestra-4,9(10),11-trien-3-one

71. Estra-4,9,11-trien-3-one, 17beta-hydroxy-17-methyl- (8ci)

72. 17-beta-hydroxy-17-methyl-19-norandrosta-4,9,11-triene-3-one

73. Estra-4,11-trien-3-one, 17-hydroxy-17-methyl-, (17.beta.)-

74. Estra-4,9,11-trien-3-one, 17beta-hydroxy-17-methyl- (7ci,8ci)

75. Estra-4,9,11-trien-3-one, 17-hydroxy-17-methyl-, (17beta)- (9ci)

76. Methyltrienolone; 17beta-hydroxy-17methyl-19norandrosta-4,9,11-trien-3-one; R1881

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 284.4 g/mol
Molecular Formula C19H24O2
XLogP32.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass284.177630004 g/mol
Monoisotopic Mass284.177630004 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count21
Formal Charge0
Complexity609
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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