Volasertib

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Also known as: 755038-65-4, Bi 6727, Volasertib (bi 6727), Bi-6727, Bi6727 (volasertib), Volasertib [usan]

Molecular Formula

C₃₄H₅₀N₈O₃

Molecular Weight

618.8 g/mol

InChI Key

SXNJFOWDRLKDSF-XKHVUIRMSA-N

FDA UNII

6EM57086EA

Volasertib is a dihydropteridinone Polo-like kinase 1 (Plk1) inhibitor with potential antineoplastic activity. Volasertib selectively inhibits Plk1, inducing selective G2/M arrest followed by apoptosis in a variety of tumor cells while causing reversible cell arrest at the G1 and G2 stage without apoptosis in normal cells. Plk1, named after the polo gene of Drosophila melanogaster, is a serine/threonine protein kinase involved in regulating mitotic spindle function in a non-ATP competitive manner.

1 2D Structure

Volasertib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[4-[4-(cyclopropylmethyl)piperazin-1-yl]cyclohexyl]-4-[[(7R)-7-ethyl-5-methyl-6-oxo-8-propan-2-yl-7H-pteridin-2-yl]amino]-3-methoxybenzamide

2.1.2 InChI

InChI=1S/C34H50N8O3/c1-6-28-33(44)39(4)29-20-35-34(38-31(29)42(28)22(2)3)37-27-14-9-24(19-30(27)45-5)32(43)36-25-10-12-26(13-11-25)41-17-15-40(16-18-41)21-23-7-8-23/h9,14,19-20,22-23,25-26,28H,6-8,10-13,15-18,21H2,1-5H3,(H,36,43)(H,35,37,38)/t25?,26?,28-/m1/s1

2.1.3 InChI Key

SXNJFOWDRLKDSF-XKHVUIRMSA-N

2.1.4 Canonical SMILES

CCC1C(=O)N(C2=CN=C(N=C2N1C(C)C)NC3=C(C=C(C=C3)C(=O)NC4CCC(CC4)N5CCN(CC5)CC6CC6)OC)C

2.1.5 Isomeric SMILES

CC[C@@H]1C(=O)N(C2=CN=C(N=C2N1C(C)C)NC3=C(C=C(C=C3)C(=O)NC4CCC(CC4)N5CCN(CC5)CC6CC6)OC)C

2.2 Other Identifiers

2.2.1 UNII

6EM57086EA

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bi 6727

2. Bi-6727

2.3.2 Depositor-Supplied Synonyms

1. 755038-65-4

2. Bi 6727

3. Volasertib (bi 6727)

4. Bi-6727

5. Bi6727 (volasertib)

6. Volasertib [usan]

7. 6em57086ea

8. Volasertib (usan)

9. Bi6727

10. Bi6727(volasertib)

11. Benzamide, N-(trans-4-(4-(cyclopropylmethyl)-1-piperazinyl)cyclohexyl)-4-(((7r)-7-ethyl-5,6,7,8-tetrahydro-5-methyl-8-(1-methylethyl)-6-oxo-2-pteridinyl)amino)-3-methoxy-

12. N-((1s,4s)-4-(4-(cyclopropylmethyl)piperazin-1-yl)cyclohexyl)-4-(((r)-7-ethyl-8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)amino)-3-methoxybenzamide

13. N-(trans-4-(4-(cyclopropylmethyl)piperazin-1-yl)cyclohexyl)-4-(((r)-7-ethyl-8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)amino)-3-methoxybenzamide

14. N-{trans-4-[4-(cyclopropylmethyl)piperazin-1-yl]cyclohexyl}-4-{[(7r)-7-ethyl-5-methyl-8-(1-methylethyl)-6-oxo-5,6,7,8-tetrahydropteridin-2-yl]amino}-3-methoxybenzamide

15. Volasertib [usan:inn]

16. Unii-6em57086ea

17. Ibi

18. N-(trans-4-(4-(cyclopropylmethyl)piperazin-1-yl)cyclohexyl)-4-(((7r)-7-ethyl-5-methyl-8-(1-methylethyl)-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)amino)-3-methoxybenzamide

19. Bi6727,volasertib

20. Volasertib(bi6727)

21. Volasertib [inn]

22. Bi6727 - Volasertib

23. Volasertib [who-dd]

24. Mls006011195

25. Schembl738946

26. Gtpl7947

27. Schembl2169101

28. Schembl9888052

29. Chembl1233528

30. Chembl4284151

31. Schembl21916558

32. Bcpp000341

33. Dtxsid801099395

34. Dtxsid901025694

35. Bcp02405

36. Ex-a1364

37. Bdbm50402023

38. Mfcd20926414

39. Nsc757149

40. Nsc800965

41. S2235

42. Zinc39716290

43. Akos030257530

44. Zinc100071772

45. Zinc248087828

46. Bcp9000403

47. Ccg-264952

48. Cs-0274

49. Db12062

50. Nsc-757149

51. Nsc-800965

52. Ncgc00263087-01

53. Ncgc00263087-02

54. Ncgc00263087-03

55. Ncgc00263087-12

56. Ncgc00263087-15

57. Ncgc00485964-01

58. Ac-32844

59. As-16996

60. Hy-12137

61. N-[4-[4-(cyclopropylmethyl)piperazin-1-yl]cyclohexyl]-4-[[(7r)-7-ethyl-5-methyl-6-oxo-8-propan-2-yl-7h-pteridin-2-yl]amino]-3-methoxybenzamide

62. Smr004702964

63. Sw218140-2

64. D10182

65. Sr-03000003275

66. Q7939986

67. Sr-03000003275-1

68. 755038-54-1

69. N-((trans)-4-(4-(cyclopropylmethyl)piperazin-1-yl)cyclohexyl)-4-((r)-7-ethyl-8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-ylamino)-3-methoxybenzamide

70. N-[cis-4-[4-(cyclopropylmethyl)-1-piperazinyl]cyclohexyl]-4-[[(7r)-7-ethyl-5,6,7,8-tetrahydro-5-methyl-8-(1-methylethyl)-6-oxo-2-pteridinyl]amino]-3-methoxybenzamide

71. N-[trans-4-[4-(cyclopropylmethyl)-1-piperazinyl]cyclohexyl]-4-[[(7r)-7-ethyl-5,6,7,8-tetrahydro-5-methyl-8-(1-methylethyl)-6-oxo-2-pteridinyl]amino]-3-methoxybenzamide

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₃₄H₅₀N₈O₃
Molecular Weight	618.8 g/mol
XLogP3	4.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	10
Exact Mass	618.40058749 g/mol
Monoisotopic Mass	618.40058749 g/mol
Topological Polar Surface Area	106 Å²
Heavy Atom Count	45
Formal Charge	0
Complexity	996
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1