Ipatasertib

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Also known as: Gdc-0068, 1001264-89-6, Ipatasertib (gdc-0068), Rg7440, Rg-7440, Gdc0068

Molecular Formula

C₂₄H₃₂ClN₅O₂

Molecular Weight

458.0 g/mol

InChI Key

GRZXWCHAXNAUHY-NSISKUIASA-N

FDA UNII

524Y3IB4HQ

Ipatasertib is an orally bioavailable inhibitor of the serine/threonine protein kinase Akt (protein kinase B) with potential antineoplastic activity. Ipatasertib binds to and inhibits the activity of Akt in a non-ATP-competitive manner, which may result in the inhibition of the PI3K/Akt signaling pathway and tumor cell proliferation and the induction of tumor cell apoptosis. Activation of the PI3K/Akt signaling pathway is frequently associated with tumorigenesis and dysregulated PI3K/Akt signaling may contribute to tumor resistance to a variety of antineoplastic agents.

1 2D Structure

Ipatasertib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-(4-chlorophenyl)-1-[4-[(5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-ylamino)propan-1-one

2.1.2 InChI

InChI=1S/C24H32ClN5O2/c1-15(2)26-13-19(17-4-6-18(25)7-5-17)24(32)30-10-8-29(9-11-30)23-21-16(3)12-20(31)22(21)27-14-28-23/h4-7,14-16,19-20,26,31H,8-13H2,1-3H3/t16-,19-,20-/m1/s1

2.1.3 InChI Key

GRZXWCHAXNAUHY-NSISKUIASA-N

2.1.4 Canonical SMILES

CC1CC(C2=C1C(=NC=N2)N3CCN(CC3)C(=O)C(CNC(C)C)C4=CC=C(C=C4)Cl)O

2.1.5 Isomeric SMILES

C[C@@H]1C[C@H](C2=C1C(=NC=N2)N3CCN(CC3)C(=O)[C@H](CNC(C)C)C4=CC=C(C=C4)Cl)O

2.2 Other Identifiers

2.2.1 UNII

524Y3IB4HQ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(4-chlorophenyl)-1-(4-(7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta(d)pyrimidin-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-one

2. Gdc-0068

3. Gdc0068

2.3.2 Depositor-Supplied Synonyms

1. Gdc-0068

2. 1001264-89-6

3. Ipatasertib (gdc-0068)

4. Rg7440

5. Rg-7440

6. Gdc0068

7. Gdc 0068

8. Gdc-0068 (rg7440)

9. 524y3ib4hq

10. (s)-2-(4-chlorophenyl)-1-(4-((5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-one

11. Chembl2177390

12. Rg 7440

13. (2s)-2-(4-chlorophenyl)-1-(4-((5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta(d)pyrimidin-4-yl)piperazin-1-yl(-3-((propan-2-yl)amino)propan-1-one

14. (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-6,7-dihydro-7-hydroxy-5-methyl-5h-cyclopentapyrimidin-4-yl]-1-piperazinyl]-3-[(1-methylethyl)amino]-1-propanone

15. (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-ylamino)propan-1-one

16. 1-propanone, 2-(4-chlorophenyl)-1-(4-((5r,7r)-6,7-dihydro-7-hydroxy-5-methyl-5h-cyclopentapyrimidin-4-yl)-1-piperazinyl)-3-((1-methylethyl)amino)-, (2s)-

17. (2s)-2-(4-chlorophenyl)-1-{4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl}-3-(propan-2-ylamino)propan-1-one

18. Ipatasertib [inn]

19. Ipatasertib [usan:inn]

20. Unii-524y3ib4hq

21. Mfcd22124514

22. 1-propanone, 2-(4-chlorophenyl)-1-[4-[(5r,7r)-6,7-dihydro-7-hydroxy-5-methyl-5h-cyclopentapyrimidin-4-yl]-1-piperazinyl]-3-[(1-methylethyl)amino]-, (2s)-

23. Gdc0068 Di-hcl

24. Ipatasertib (usan/inn)

25. Ipatasertib [usan]

26. Gdc-0068 Di-hcl

27. Ipatasertib; Gdc-0068

28. Rg-7440 Di-hcl

29. Ipatasertib [who-dd]

30. Schembl191659

31. Gtpl7887

32. Chebi:95089

33. Dtxsid101025595

34. Ex-a2077

35. Bdbm50398379

36. Nsc767898

37. Nsc781451

38. Nsc800986

39. Nsc832484

40. S2808

41. Zinc68250459

42. Akos025396463

43. Bcp9000712

44. Ccg-269312

45. Cs-0975

46. Db11743

47. Nsc-767898

48. Nsc-781451

49. Nsc-800986

50. Nsc-832484

51. Ncgc00346714-01

52. 2-(4-chlorophenyl)-1-(4-(7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta(d)pyrimidin-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-one

53. Ac-28420

54. As-17027

55. Hy-15186

56. Bcp0726000195

57. J3.478.537f

58. D10641

59. Q27078088

60. (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[e]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-ylamino)propan-1-one

61. 0rf

2.4 Create Date

2008-05-19

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₃₂ClN₅O₂
Molecular Weight	458.0 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	457.2244530 g/mol
Monoisotopic Mass	457.2244530 g/mol
Topological Polar Surface Area	81.6 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	622
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1