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Chemistry

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Also known as: 951-78-0, Deoxyuridine, Uracil deoxyriboside, Uridine, 2'-deoxy-, 2-deoxyuridine, 1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione

Molecular Formula

C₉H₁₂N₂O₅

Molecular Weight

228.20 g/mol

InChI Key

MXHRCPNRJAMMIM-SHYZEUOFSA-N

FDA UNII

W78I7AY22C

2'-Deoxyuridine. An antimetabolite that is converted to deoxyuridine triphosphate during DNA synthesis. Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies.

1 2D Structure

Deoxyuridine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

2.1.2 InChI

InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1

2.1.3 InChI Key

MXHRCPNRJAMMIM-SHYZEUOFSA-N

2.1.4 Canonical SMILES

C1C(C(OC1N2C=CC(=O)NC2=O)CO)O

2.1.5 Isomeric SMILES

C1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)O

2.2 Other Identifiers

2.2.1 UNII

W78I7AY22C

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (beta 1-(2-deoxyribopyranosyl))thymidine

2. Deoxyuridine

2.3.2 Depositor-Supplied Synonyms

1. 951-78-0

2. Deoxyuridine

3. Uracil Deoxyriboside

4. Uridine, 2'-deoxy-

5. 2-deoxyuridine

6. 1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione

7. Deoxyribose Uracil

8. 2'-desoxyuridine

9. Durd

10. 2'-deoxyuridine-1'-d

11. 1-(2-deoxy-beta-d-ribofuranosyl)uracil

12. W78i7ay22c

13. Chebi:16450

14. 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

15. Ccris 2832

16. Nsc 23615

17. Desoxyuridine

18. 1-(2-deoxy-beta-d-erythro-pentofuranoxyl)uracil

19. Uracil Desoxyuridine

20. Mfcd00006527

21. 1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydro-furan-2-yl)pyrimidine-2,4(1h,3h)-dione

22. Dur

23. 2,4(1h,3h)-pyrimidinedione, 1-(2-deoxy-beta-d-ribofuranosyl)-

24. 2,4(1h,3h)-pyrimidinedione, 1-(2-deoxy-beta-d-erythro-ribofuranosyl)-

25. Einecs 213-455-7

26. Brn 0024433

27. Unii-w78i7ay22c

28. Nsc-23615

29. 1-(2-deoxy-d-erythro-pentofuranosyl)uracil

30. Uridinie, 2'-deoxy-

31. 2yb0

32. Deoxyuridine [mi]

33. Bmse000320

34. 1-(2-deoxy-beta-d-erythro-pentofuranosyl)uracil

35. Schembl28844

36. Mls001066344

37. 2'-du

38. Chembl353955

39. 2'-deoxyuridine, >=98.5%

40. Amy6955

41. Dtxsid30883621

42. Hms2267d16

43. Zinc155696

44. Hy-d0186

45. S5505

46. Zinc00155696

47. Akos015833069

48. Akos015896792

49. 1-(2-deoxy-ss-d-ribofuranosyl)uracil

50. Ccg-247504

51. Cs-w019820

52. Db02256

53. Ps-7750

54. 1-[(4s,2r,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-dihydropyrimidine-2, 4-dione

55. Ncgc00142492-01

56. Smr000112296

57. D0060

58. 1-(2-deoxy-delta-erythro-pentofuranosyl)uracil

59. C00526

60. O10766

61. 951d780

62. Q419140

63. J-700048

64. 1-(2-deoxy-.beta.-d-erythro-pentofuranosyl)uracil

65. E73b1553-a13a-4989-b045-a589a8f2b9dc

66. 1-(2-deoxy-beta-d-ribofuranosyl)-2,4(1h,3h)-pyrimidinedione

67. 1-(2-deoxy-beta-delta-ribofuranosyl)-2,4(1h,3h)-pyrimidinedione

68. 1-(2-deoxy-beta-d-erythro-pentofuranosyl)-2,4(1h,3h)-pyrimidinedione

69. 1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-2,4(1h,3h)-pyrimidinedione

70. 1-((2r,4s,5r)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-h-pyrimidine-2,4-dione

71. 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₂N₂O₅
Molecular Weight	228.20 g/mol
XLogP3	-1.6
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	228.07462149 g/mol
Monoisotopic Mass	228.07462149 g/mol
Topological Polar Surface Area	99.1 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	343
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

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.)

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