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Vidarabine Monophosphate

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Chemistry

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Also known as: 29984-33-6, Vidarabine monophosphate, Ara-amp, Vidarabine phosphate [usan], Cl-808, 9-(5-o-phosphono-beta-d-arabinofuranosyl)adenine

Molecular Formula

C₁₀H₁₄N₅O₇P

Molecular Weight

347.22 g/mol

InChI Key

UDMBCSSLTHHNCD-UHTZMRCNSA-N

FDA UNII

106XV160TZ

An adenosine monophosphate analog in which ribose is replaced by an arabinose moiety. It is the monophosphate ester of VIDARABINE with antiviral and possibly antineoplastic properties.

1 2D Structure

Vidarabine Monophosphate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R,3S,4S,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate

2.1.2 InChI

InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7+,10-/m1/s1

2.1.3 InChI Key

UDMBCSSLTHHNCD-UHTZMRCNSA-N

2.1.4 Canonical SMILES

C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)O)O)O)N

2.1.5 Isomeric SMILES

C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N

2.2 Other Identifiers

2.2.1 UNII

106XV160TZ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 9-(5-o-phosphono-beta-d-arabinofuranosyl)-9h-purin-6-amine

2. Adenine Arabinoside Monophosphate

3. Ara Amp

4. Ara-amp

5. Arabinofuranosyladenine Monophosphate

6. Monophosphate, Adenine Arabinoside

7. Monophosphate, Arabinofuranosyladenine

8. Monophosphate, Vidarabine

9. Phosphate, Vidarabine

10. Vidarabine Monophosphate

2.3.2 Depositor-Supplied Synonyms

1. 29984-33-6

2. Vidarabine Monophosphate

3. Ara-amp

4. Vidarabine Phosphate [usan]

5. Cl-808

6. 9-(5-o-phosphono-beta-d-arabinofuranosyl)adenine

7. Ci-808

8. 9h-purin-6-amine, 9-(5-o-phosphono-beta-d-arabinofuranosyl)-

9. 9-(5-o-phosphono-beta-d-arabinofuranosyl)-9h-purin-6-amine

10. Adenine-9-beta-d-arabinofuranoside-5'-monophosphate

11. Adenine Arabinoside Monophosphate

12. Vidarabine-5'-monophosphate

13. 106xv160tz

14. Arabinosyladenine Monophosphate

15. Adenine Arabinose-5'-phosphate

16. Nsc-127223

17. Araamp

18. 5'-arabinosyladenine Monophosphate

19. 9h-purin-6-amine, 9-(5-o-phosphono-b-d-arabinofuranosyl)-

20. Adenine Arabinoside 5'-monophosphate

21. D-arabinosyladenine 5'-monophosphate

22. Adenine Arabinonucleoside 5'-phosphate

23. [(2r,3s,4s,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl Dihydrogen Phosphate

24. Vidarabine Phosphate (usan)

25. 9h-purin-6-amine,9-(5-o-phosphono-b-d-arabinofuranosyl)-

26. Vidarabinemonophosphate

27. Vidarabine 5'-monophosphate

28. Einecs 249-990-8

29. Nsc 127223

30. 9h-purin-6-amine, 9-(5-o-phosphono-.beta.-d-arabinofuranosyl)-

31. Unii-106xv160tz

32. Nsc127223

33. 9-beta-d-arabinofuranosyladenine 5'-phosphate

34. 9-beta-d-arabinofuranosyladenine Monophosphate

35. Arabino-amp

36. 9-beta-d-arabinofuranosyladenine 5'-monophosphate

37. Mfcd00069723

38. 9-beta-d-arabinofuranosyladenine 5'-(dihydrogen Phosphate)

39. Adenine, 9beta-d-arabinofuranosyl-, 5'-(dihydrogen Phosphate)

40. Schembl144996

41. Chembl1230732

42. Hy-b0277a

43. Adenosine Arabinoside-5'-phosphate

44. Dtxsid401009318

45. Adenine, 9-beta-d-arabinofuranosyl-, 5'-(dihydrogen Phosphate)

46. Bcp10479

47. Zinc2126310

48. Hg1004

49. Vidarabine Phosphate [mart.]

50. Vidarabine Phosphate [who-dd]

51. Akos015915213

52. Ac-5505

53. Am84913

54. ((2r,3s,4s,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl Dihydrogen Phosphate

55. [(2r,3s,4s,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl Dihydrogen Phosphate

56. As-70487

57. Ara-adenosine-5'-monophosphate (ara-amp)

58. Cs-0083442

59. D06299

60. 9-(b-d-arabinofuranosyl)adenine5'-monophosphate

61. 9-(b-d-arabinofuranosyl)adenine 5'-monophosphate

62. 9-beta-d-arabinofuranosyladenine-5'-monophosphate

63. 984a336

64. A820136

65. 9-(.beta.-d-arabinofuranosyl)adenine-5'-phosphate

66. Q6607436

67. W-202244

68. 9-beta-d-arabinofuranosyl-adenine-5'-monophosphate

69. 9h-purin-6-amine, 9-(5-o-phosphono-b-d-arabinofuranosyl)-;

70. 9-.beta.-d-arabinofuranosyladenine 5'-(dihydrogen Phosphate)

71. {[(2r,3s,4s,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic Acid

72. A5o

2.4 Create Date

2005-07-12

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₄N₅O₇P
Molecular Weight	347.22 g/mol
XLogP3	-3.5
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	4
Exact Mass	347.06308480 g/mol
Monoisotopic Mass	347.06308480 g/mol
Topological Polar Surface Area	186 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	481
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
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

Antimetabolites

Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)

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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