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Distamycin A

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Chemistry

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Also known as: Distamycin a, Distamycin, 636-47-5, Herperetin, Stallimycin [inn], Dst-a

Molecular Formula

C₂₂H₂₇N₉O₄

Molecular Weight

481.5 g/mol

InChI Key

UPBAOYRENQEPJO-UHFFFAOYSA-N

FDA UNII

80O63P88IS

Stallimycin is an oligopeptide antineoplastic antibiotic isolated from the bacterium Streptomyces distallicus. Distamycin preferentially binds to adenine-thymine (A-T) rich sequences in the minor groove of DNA, thereby inhibiting DNA replication and RNA transcription. In addition to antitumor effects, distamycin also possesses antiviral and antiprotozoal activities and is used as a chromosome dye. (NCI04)

1 2D Structure

Distamycin A

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[5-[[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-formamido-1-methylpyrrole-2-carboxamide

2.1.2 InChI

InChI=1S/C22H27N9O4/c1-29-9-13(26-12-32)6-17(29)21(34)28-15-8-18(31(3)11-15)22(35)27-14-7-16(30(2)10-14)20(33)25-5-4-19(23)24/h6-12H,4-5H2,1-3H3,(H3,23,24)(H,25,33)(H,26,32)(H,27,35)(H,28,34)

2.1.3 InChI Key

UPBAOYRENQEPJO-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1C=C(C=C1C(=O)NC2=CN(C(=C2)C(=O)NC3=CN(C(=C3)C(=O)NCCC(=N)N)C)C)NC=O

2.2 Other Identifiers

2.2.1 UNII

80O63P88IS

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Distamycin

2. Distamycin A

3. Stallimycin Hydrochloride

4. Stallimycin Monohydrochloride

2.3.2 Depositor-Supplied Synonyms

1. Distamycin A

2. Distamycin

3. 636-47-5

4. Herperetin

5. Stallimycin [inn]

6. Dst-a

7. Nsc82150

8. Nsc-82150

9. Fi 6426

10. Chembl11252

11. 80o63p88is

12. N-[5-[[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-formamido-1-methylpyrrole-2-carboxamide

13. Ncgc00018292-04

14. Distamycin 3

15. Nsc 150528

16. Estalimicina

17. Stallimicina

18. Stallimycine

19. Stallimycinum

20. Distamicina A

21. Distamycin Hydrochloride

22. 1h-pyrrole-2-carboxamide, N-(5-(((3-amino-3-iminopropyl)amino)carbonyl)-1-methyl-1h-pyrrol-3-yl)-4-(((4-(formylamino)-1-methyl-1h-pyrrol-2-yl)carbonyl)amino)-1-methyl-

23. 1h-pyrrole-2-carboxamide, N-[5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1h-pyrrol-3-yl]-4-[[[4-(formylamino)-1-methyl-1h-pyrrol-2-yl]carbonyl]amino]-1-methyl-

24. Nsc150528

25. Stallimicina [dcit]

26. Distamicina A [italian]

27. Stallimycine [inn-french]

28. Stallimycinum [inn-latin]

29. Estalimicina [inn-spanish]

30. Unii-80o63p88is

31. Nsc 82150

32. Brn 0468437

33. Dst-3

34. Distamycin A [mi]

35. Dsstox_cid_25637

36. Dsstox_rid_81018

37. Dsstox_gsid_45637

38. Distamycin; Stallimycin

39. Schembl108585

40. Dtxsid9045637

41. Cid_6602691

42. Zinc3872327

43. Tox21_110857

44. Bdbm50055659

45. Ccg-36393

46. N''-(2-amidinoethyl)-4-formamido-1,1',1''-trimethyl-n-4':n'-4''-ter-(2-pyrrolcarboxamid)

47. Ncgc00018292-01

48. Ncgc00018292-02

49. Ncgc00018292-03

50. Ncgc00018292-05

51. Ncgc00024382-03

52. Cas-636-47-5

53. Nci60_041805

54. Sr-01000000269

55. Sr-01000000269-3

56. Q27269162

57. N,4''-ter[pyrrole-2-carboxamide], N''-(2-amidinoethyl)-4-formamido-1,1',1''-trimethyl-

58. (n,4':n',4''-terpyrrole)-2-carboxamide, N''-(2-amidinoethyl)-4-formamido-1,1',1''-trimethyl-

59. 2n-(3,3-aminoiminopropyl)-4-[4-(4-formamido-1-methyl-1h-2-pyrrolylcarboxamido)-1-methyl-1h-2-pyrrolylcarboxamido]-1-methyl-1h-2-pyrrolecarboxamide

60. 2n-[5-(3-amino-3-iminopropylcarbamoyl)-1-methyl-1h-3-pyrrolyl]-4-(4-formamido-1-methyl-1h-2-pyrrolylcarboxamido)-1-methyl-1h-2-pyrrolecarboxamide

61. 2n-[5-(3-amino-3-iminopropylcarbamoyl)-1-methyl-1h-3-pyrrolyl]-4-(4-formamido-1-methyl-1h-2-pyrrolylcarboxamido)-1-methyl-1h-2-pyrrolecarboxamide(distamycin A)

62. 2n-[5-(3-amino-3-iminopropylcarbamoyl)-1-methyl-1h-3-pyrrolyl]-4-(4-formamido-1-methyl-1h-2-pyrrolylcarboxamido)-1-methyl-1h-2-pyrrolecarboxamide(distamycin)

63. 39389-47-4

64. 4n-[5-(3-amino-3-iminopropylcarbamoyl)-1-methyl-1h-2-pyrrolyl]-2-(4-formamido-1-methyl-1h-2-pyrrolylcarboxamido)-1-methyl-1h-4-pyrrolecarboxamide

65. 5n-[5-(3-amino-3-iminopropylcarbamoyl)-1-methyl-2,3-dihydro-1h-3-pyrrolyl]-3-(4-formamido-1-methyl-1h-2-pyrrolylcarboxamido)-1-methyl-2,3-dihydro-1h-5-pyrrolecarboxamide

66. N''-(2-amidinoethyl)-4-formamido-1,1',1''-trimethyl-n,4':n',4''-ter(pyrrole-2-carboxamide)

67. N-(3-amino-3-iminopropyl)-4-(4-(4-formamido-1-methyl-1h-pyrrole-2-carboxamido)-1-methyl-1h-pyrrole-2-carboxamido)-1-methyl-1h-pyrrole-2-carboxamide

68. N-[5-({5-[(3-amino-3-iminopropyl)carbamoyl]-1-methyl-1h-pyrrol-3-yl}carbamoyl)-1-methyl-1h-pyrrol-3-yl]-4-(formylamino)-1-methyl-1h-pyrrole-2-carboxamide

69. N-[5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1h-pyrrol-3-yl]-4-[[[4-(formylamino)-methyl-1h-pyrrol-2-yl]carbonyl]amino]-1h-pyrrole-2-carboxamide

70. N-[5-[[(amino-3-iminopropyl)amino]carbonyl]-1-methyl-1h-pyrrol-3-yl-4-[[(4-(formylamino)-1-methyl-1h-pyrrol-2yl]carbonyl]amino]-1h-pyrrole-2-carboxamide

71. N-[5-[[5-[(3-amino-3-imino-propyl)carbamoyl]-1-methyl-pyrrol-3-yl]carbamoyl]-1-methyl-pyrrol-3-yl]-4-formamido-1-methyl-pyrrole-2-carboxamide

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₇N₉O₄
Molecular Weight	481.5 g/mol
XLogP3	-1.8
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	9
Exact Mass	481.21860038 g/mol
Monoisotopic Mass	481.21860038 g/mol
Topological Polar Surface Area	181 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	825
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

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