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Aphidicolin
Also known as: 38966-21-1, (+)-aphidicolin, (+/-)-aphidicolin, Ici 69653, Nsc-234714, Aphidicolin, (+/-)-
Molecular Formula
C20H34O4
Molecular Weight
338.5  g/mol
InChI Key
NOFOAYPPHIUXJR-APNQCZIXSA-N
FDA UNII
192TJ6PP19

An antiviral antibiotic produced by Cephalosporium aphidicola and other fungi. It inhibits the growth of eukaryotic cells and certain animal viruses by selectively inhibiting the cellular replication of DNA polymerase II or the viral-induced DNA polymerases. The drug may be useful for controlling excessive cell proliferation in patients with cancer, psoriasis or other dermatitis with little or no adverse effect upon non-multiplying cells.
1 2D Structure

Aphidicolin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,2S,5R,6R,7R,10S,12R,13R)-6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol
2.1.2 InChI
InChI=1S/C20H34O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-16,21-24H,3-12H2,1-2H3/t13-,14+,15-,16+,17-,18-,19-,20-/m0/s1
2.1.3 InChI Key
NOFOAYPPHIUXJR-APNQCZIXSA-N
2.1.4 Canonical SMILES
CC12CCC(C(C1CCC3C24CCC(C(C3)C4)(CO)O)(C)CO)O
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]([C@@]([C@@H]1CC[C@@H]3[C@@]24CC[C@@]([C@H](C3)C4)(CO)O)(C)CO)O
2.2 Other Identifiers
2.2.1 UNII
192TJ6PP19
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Aphidicolin, (3-s-(3alpha,4beta,4abeta,6aalpha,8alpha,9alpha,11aalpha,11balpha))-isomer

2. Ici 69653

3. Ici-69653

4. Ici69653

5. Nsc 234714

6. Nsc 351140

7. Nsc-234714

8. Nsc-351140

9. Nsc234714

10. Nsc351140

2.3.2 Depositor-Supplied Synonyms

1. 38966-21-1

2. (+)-aphidicolin

3. (+/-)-aphidicolin

4. Ici 69653

5. Nsc-234714

6. Aphidicolin, (+/-)-

7. (3r,4r,4ar,6as,8r,9r,11as,11bs)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalene-3,9-diol

8. Nsc234714

9. 6b3f8qw8tu

10. Chembl29711

11. Mls000069677

12. Chebi:2766

13. 69926-98-3

14. 192tj6pp19

15. 9,15-cyclo-c,18-dinor-14,15-secoandrostane-4,17-dimethanol, 3,17-dihydroxy-4-methyl-, (3alpha,4alpha,5alpha,17alpha)-

16. Smr000058538

17. 8,11

18. A-methano-11ah-cyclohepta[a]naphthalene-4,9-dimethanol,tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-, (3r,4r,4ar,6as,8r,9r,11as,11bs)-

19. 8,11a-methano-11ah-cyclohepta(a)naphthalene-4,9-dimethanol, Tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-, (3r,4r,4ar,6as,8r,9r,11as,11bs)-rel-

20. Rel-(3r,4r,4ar,6as,8r,9r,11as,11bs)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalene-3,9-diol

21. Nsc 234714

22. Ccris 1783

23. Ici-69653

24. Mfcd00083214

25. Unii-6b3f8qw8tu

26. Aphidicholin

27. Aphidocolin

28. Brn 4689958

29. Unii-192tj6pp19

30. Bis(hydroxymethyl)-dimethyl-[?]diol

31. Aphidicolin From Nigrospora Sphaerica

32. Ne-3,9-diol

33. Aphidicolin [mi]

34. Opera_id_1321

35. Cbiol_001873

36. Bspbio_001438

37. Kbiogr_000158

38. Kbioss_000158

39. Schembl183956

40. Cid_457964

41. Megxm0_000277

42. Aphidicolin, Analytical Standard

43. Dtxsid5036711

44. Acon0_000080

45. Acon1_000511

46. Bcbcmap01_000163

47. Kbio2_000158

48. Kbio2_002726

49. Kbio2_005294

50. Kbio3_000315

51. Kbio3_000316

52. Bio1_000159

53. Bio1_000648

54. Bio1_001137

55. Bio2_000158

56. Bio2_000638

57. Hms1361h20

58. Hms1791h20

59. Hms1989h20

60. Hms3402h20

61. Hy-n6733

62. Zinc3789195

63. Bdbm50090910

64. Akos027470273

65. Aphidicolin - Cas 38966-21-1

66. At25347

67. Ccg-208640

68. Idi1_033908

69. Smp1_000025

70. Ncgc00023142-03

71. Ncgc00023142-04

72. Ncgc00023142-05

73. Ncgc00023142-06

74. 8,11a-methano-11ah-cyclohepta(a)naphthalene-4,9-dimethanol, Tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-, (3r-(3-alpha,4-alpha,4a-alpha,6a-beta,8-beta,9-beta,11a-beta,11b-beta))-

75. Ba162709

76. 3alpha,16,17,18-tetrahydroxyaphidicolone

77. Cs-0033151

78. 966a211

79. Q27453425

80. 4b15b386-8738-48fe-80db-5ba3406098dd

81. Aphidicolin From Nigrospora Sphaerica, >=98% (hplc), Powder

82. (1s,2s,5r,6r,7r,10s,12r,13r)-6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.0[1,10].0[2,7]]hexadecane-5,13-diol

83. (3alpha,4alpha,5alpha,17alpha)-3,17-dihydroxy-4-methyl-9,15-cyclo-c,18-dinor-14,15-secoandrostane-4,17-dimethanol

84. (3r,4r,4ar,6as,8r,9r,11as,11bs)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta[a]naphthale

85. (3r,4r,4ar,6as,8r,9r,11as,11bs)-tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-8,11a-methano-11ah-cyclohepta[a]naphthalene-4,9-dimethanol

86. 2ze

87. 6,13-di(hydroxymethyl)-2,6-dimethyl-(1s,2s,5r,6r,7r)-tetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol

88. 6,13-di(hydroxymethyl)-2,6-dimethyl-(1s,2s,5r,6r,7r,10s,12r,13r)-tetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol (aphidicolin)

89. 6,13-di(hydroxymethyl)-2,6-dimethyl-(1s,2s,5r,6r,7r,10s,12r,13r)-tetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol(aphidicolin)

90. 8,11a-methano-11ah-cyclohepta(a)naphthalene-4,9-dimethanol, Tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-, (3r,4r,4ar,6as,8r,9r,11as,11bs)-

91. 8,11a-methano-11ah-cyclohepta[a]naphthalene-4,9-dimethanol, Tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-, (3s,4r,4ar,6as,8r,9r,11as,11bs)-

92. 9,15-cyclo-c,18-dinor-14,15-secoandrostane-4,17-dimethanol, 3,17-dihydroxy-4-methyl-, (3.alpha.,4.alpha.,5.alpha.,17.alpha.)-

2.4 Create Date
2005-06-29
3 Chemical and Physical Properties
Molecular Weight 338.5 g/mol
Molecular Formula C20H34O4
XLogP32.5
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass338.24570956 g/mol
Monoisotopic Mass338.24570956 g/mol
Topological Polar Surface Area80.9 Ų
Heavy Atom Count24
Formal Charge0
Complexity524
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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.)


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.)


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