9-Aminocamptothecin

Synopsis, Chemistry

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Also known as: 91421-43-1, Aminocamptothecin, 9-amino-camptothecin, 9-amino-cpt, 9-amino-20(s)-camptothecin, 9-amino-20-(s)-camptothecin

Molecular Formula

C₂₀H₁₇N₃O₄

Molecular Weight

363.4 g/mol

InChI Key

FUXVKZWTXQUGMW-FQEVSTJZSA-N

FDA UNII

5MB77ICE2Q

Aminocamptothecin is a water-insoluble camptothecin derivative. Aminocamptothecin binds to the nuclear enzyme topoisomerase I, thereby inhibiting repair of single-strand DNA breakages. Because the terminal lactone ring of aminocamptothecin required for the agent's antitumor activity spontaneously opens under physiological conditions to an inactive carboxy form, the drug must be administered over an extended period of time to achieve effective cytotoxicity. (NCI04)

1 2D Structure

9-Aminocamptothecin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(19S)-8-amino-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

2.1.2 InChI

InChI=1S/C20H17N3O4/c1-2-20(26)13-7-16-17-10(6-11-14(21)4-3-5-15(11)22-17)8-23(16)18(24)12(13)9-27-19(20)25/h3-7,26H,2,8-9,21H2,1H3/t20-/m0/s1

2.1.3 InChI Key

FUXVKZWTXQUGMW-FQEVSTJZSA-N

2.1.4 Canonical SMILES

CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC=C5N=C4C3=C2)N)O

2.1.5 Isomeric SMILES

CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC=C5N=C4C3=C2)N)O

2.2 Other Identifiers

2.2.1 UNII

5MB77ICE2Q

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 9-amino-20(s)-camptothecin

2. 9-amino-20-camptothecin, (+-)-isomer

3. 9-amino-20-camptothecin, (r,s)-isomer

4. 9-amino-cpt

5. Nsc 603071

2.3.2 Depositor-Supplied Synonyms

1. 91421-43-1

2. Aminocamptothecin

3. 9-amino-camptothecin

4. 9-amino-cpt

5. 9-amino-20(s)-camptothecin

6. 9-amino-20-(s)-camptothecin

7. Nsc-603071

8. Nsc603071

9. 5mb77ice2q

10. Chembl274070

11. (s)-10-amino-4-ethyl-4-hydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

12. Chebi:80755

13. (s)-10-amino-4-ethyl-4-hydroxy-1h-pyrano[3',4':6,7]-indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

14. Camptothecin, 9-amino-

15. (19s)-8-amino-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

16. (s)-10-amino-4-ethyl-4-hydroxy-1,12-dihydro-14h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h)-dione

17. 10-amino-4(s)-4-ethyl-4-hydroxy-1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione

18. 10-amino-4(s)-4-ethyl-4-hydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

19. Mls002702905

20. Unii-5mb77ice2q

21. Nsc 603071

22. Idec-132

23. Nsc-629971

24. 9-aminocamptothecan

25. 9-amino Camptothecin

26. 9-nh2-camptothecin

27. 9-amino-2(s)-camptothecin

28. Schembl26578

29. (s)-10-amino-4-ethyl-4-hydroxy-1h-pyrano(3;,4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione

30. Cid_72402

31. Mls000728575

32. 9-aminocamptothecin [mi]

33. Dtxsid10873202

34. Hms2220k11

35. Hms3339h11

36. Hms3749c03

37. 10-amino-4-ethyl-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

38. Bcp09002

39. Ex-a4335

40. 9-amino-cpt (9-aminocamptothecin)

41. Bdbm50008936

42. Mfcd00909855

43. S2653

44. Zinc37866089

45. 9-aminocamptothecin [who-dd]

46. Akos015896595

47. Cs-7784

48. Db12515

49. Ncgc00247552-01

50. 1h-pyrano(3;,4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 10-amino-4-ethyl-4-hydroxy-, (s)-

51. Ac-33991

52. As-14292

53. Nci60_004578

54. Smr000445687

55. Hy-100309

56. F11420

57. 421a431

58. A843867

59. J-504140

60. Brd-k09291936-001-07-5

61. Q27149808

62. (s)-10-amino-4-ethyl-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

63. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 10-amino-4-ethyl-4-hydroxy-, (4s)-

64. 1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione,4-ethyl-4-hydroxy-9-nitro-

65. 1h-pyrano[3',7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione, 10-amino-4-ethyl-4-hydroxy-, (s)-

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₇N₃O₄
Molecular Weight	363.4 g/mol
XLogP3	0.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	1
Exact Mass	363.12190603 g/mol
Monoisotopic Mass	363.12190603 g/mol
Topological Polar Surface Area	106 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	775
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