AM 2282

Synopsis, Chemistry

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Also known as: Staurosporin, 62996-74-1, (+)-staurosporine, Antibiotic 230, Am-2282, Antibiotic am 2282

Molecular Formula

C₂₈H₂₆N₄O₃

Molecular Weight

466.5 g/mol

InChI Key

HKSZLNNOFSGOKW-FYTWVXJKSA-N

FDA UNII

H88EPA0A3N

An indolocarbazole that is a potent PROTEIN KINASE C inhibitor which enhances cAMP-mediated responses in human neuroblastoma cells. (Biochem Biophys Res Commun 1995;214(3):1114-20)

1 2D Structure

AM-2282

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3R,4R,6R)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one

2.1.2 InChI

InChI=1S/C28H26N4O3/c1-28-26(34-3)17(29-2)12-20(35-28)31-18-10-6-4-8-14(18)22-23-16(13-30-27(23)33)21-15-9-5-7-11-19(15)32(28)25(21)24(22)31/h4-11,17,20,26,29H,12-13H2,1-3H3,(H,30,33)/t17-,20-,26-,28+/m1/s1

2.1.3 InChI Key

HKSZLNNOFSGOKW-FYTWVXJKSA-N

2.1.4 Canonical SMILES

CC12C(C(CC(O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)CNC6=O)NC)OC

2.1.5 Isomeric SMILES

C[C@@]12[C@@H]([C@@H](C[C@@H](O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)CNC6=O)NC)OC

2.2 Other Identifiers

2.2.1 UNII

H88EPA0A3N

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 8,12-epoxy-1h,8h-2,7b,12a-triazadibenzo(a,g)cyclonona(cde)trinden-1-one, 2,3,9,10,11,12-hexahydro-9-methoxy-8-methyl-10-(methylamino)-, (8alpha,9beta,10beta,12alpha)-(+)-

2.3.2 Depositor-Supplied Synonyms

1. Staurosporin

2. 62996-74-1

3. (+)-staurosporine

4. Antibiotic 230

5. Am-2282

6. Antibiotic Am 2282

7. Ccris 3272

8. Antibiotic Am-2282

9. Alkaloid Am-2282 From Streptomyces

10. H88epa0a3n

11. Chembl388978

12. Chebi:15738

13. C28h26n4o3

14. 8,12-epoxy-1h,8h-2,7b,12a-triazadibenzo(a,g)cyclonona(cde)trinden-1-one, 2,3,9,10,11,12-hexahydro-9-methoxy-8-methyl-10-(methylamino)-, (8alpha,9beta,10beta,12alpha)-(+)-

15. (5s,6r,7r,9r)-6-methoxy-5-methyl-7-(methylamino)-6,7,8,9,15,16-hexahydro-5h,14h-17-oxa-4b,9a,15-triaza-5,9-methanodibenzo[b,h]cyclonona[jkl]cyclopenta[e]-as-indacen-14-one

16. (5s,6r,7r,9r)-6-methoxy-5-methyl-7-methylamino-6,7,8,9,15,16-hexahydro-5h,14h-5,9-epoxy-4b,9a,15-triazadibenzo[b,h]cyclonona[1,2,3,4-jkl]cyclopenta[e]-as-indacen-14-one

17. Unii-h88epa0a3n

18. Gnf-pf-1389

19. Methoxy-methyl-(methylamino)[?]one

20. Sr-00000001485

21. Cgp-39360

22. Dtxsid6041131

23. Staurosporin, 4

24. 1nvr

25. 1stc

26. 1xbc

27. 1xjd

28. 1yhs

29. 2gcd

30. Staurosporine, 8

31. Cgp 39360

32. Staurosporine & Tnf

33. 1q3d

34. 1sm2

35. 2dq7

36. Staurosporine [mi]

37. Molmap_000047

38. Schembl8157

39. Cbiol_001978

40. Bspbio_001146

41. Gtpl346

42. Bdbm2579

43. Megxm0_000307

44. 1u59

45. Bcpp000063

46. Bio1_000264

47. Bio1_000753

48. Bio1_001242

49. Hms1990j07

50. Hms3650b17

51. Ex-a1777

52. Zinc3814434

53. Am2282

54. Mfcd18252446

55. Nsc755774

56. S1421

57. Staurosporin And Antibiotic Am-2282

58. Akos015897119

59. Am 2282

60. Ccg-208052

61. Db02010

62. Nsc-755774

63. Qtl1_000078

64. Ncgc00162400-01

65. Ncgc00162400-02

66. Ncgc00162400-03

67. Ncgc00162400-04

68. Ncgc00162400-05

69. Ncgc00162400-06

70. Ncgc00162400-09

71. 9,13-epoxy-1h,9h-diindolo(1,2,3-gh:3',2',1'-lm)pyrrolo(3,4-j)(1,7)-benzodiazonin-1-one, 2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-11-(methylamino)-, (9s-(9alpha,10beta,11beta,13alpha)-

72. Ac-35765

73. Hy-15141

74. Staurosporine & Tumor Necrosis Factor (tnf)

75. Staurosporine 100 Microg/ml In Acetonitrile

76. T4000

77. Q5957181

78. Sr-00000001485-4

79. Brd-k17953061-001-02-8

80. Brd-k17953061-001-04-4

81. Brd-k17953061-001-05-1

82. Brd-k17953061-001-08-5

83. Brd-k17953061-001-10-1

84. Brd-k17953061-001-11-9

85. (2s,3r,4r,6r)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^{2,6}.0^{7,28}.0^{8,13}.0^{15,19}.0^{20,27}.0^{21,26}]nonacosa-8(13),9,11,14(28),15(19),20(27),21(26),22,24-nonaen-16-one

86. (2s,3r,4r,6r)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^{2,6}.0^{7,28}.0^{8,13}.0^{15,19}.0^{20,27}.0^{21,26}]nonacosa-8,10,12,14(28),15(19),20(27),21,23,25-nonaen-16-one

87. (2s,3r,4r,6r)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one

88. (5s,6r,7r,9r)-6-methoxy-5-methyl-7-(methylamino)-6,7,8,9,15,16-hexahydro-5h,14h-5,9-epoxy-4b,9a,15-triazadibenzo[b,h]cyclonona[1,2,3,4-jkl]cyclopenta[e]-as-indacen-14-one

89. (9s,10r,11r,13r)- 2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-11-(methylamino)-9,13-epoxy-1h,9h-diindolo(1,2,3-gh:3',2',1'-lm)pyrrolo(3,4-j)(1,7)benzodiazonin-1-one

90. [9s-(9?,10?,11?,13?)]-2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-11-(methylamino)-9,13-epoxy-1h,9h-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one

91. 109189-95-9

92. 9,13-epoxy-1h,9h-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one, 2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-11-(methylamino)-, (9s,10r,11r,13r)- & Tumor Necrosis Factor (tnf)

93. 9,13-epoxy-1h,9h-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one, 2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-11-(methylamino)-, (9s,10r,11r,13r)- (9ci)

94. 9,13-epoxy-1h,9h-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one, 2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-11-(methylamino)-, [9s-(9alpha,10beta,11beta,13alpha)]-

2.4 Create Date

2005-06-08

3 Chemical and Physical Properties

Molecular Formula	C₂₈H₂₆N₄O₃
Molecular Weight	466.5 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	466.20049070 g/mol
Monoisotopic Mass	466.20049070 g/mol
Topological Polar Surface Area	69.4 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	901
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)