Uridine-5'-diphosphate-glucose

Synopsis, Chemistry

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Also known as: Udp-glucose, Uridine diphosphate glucose, Udpg, 133-89-1, Udp-alpha-d-glucose, Co-waldenase

Molecular Formula

C₁₅H₂₄N₂O₁₇P₂

Molecular Weight

566.30 g/mol

InChI Key

HSCJRCZFDFQWRP-JZMIEXBBSA-N

FDA UNII

V50K1D7P4Y

A key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.

1 2D Structure

Uridine-5

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate

2.1.2 InChI

InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1

2.1.3 InChI Key

HSCJRCZFDFQWRP-JZMIEXBBSA-N

2.1.4 Canonical SMILES

C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OC3C(C(C(C(O3)CO)O)O)O)O)O

2.1.5 Isomeric SMILES

C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

V50K1D7P4Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Diphosphate Glucose, Uridine

2. Diphosphoglucose, Uridine

3. Glucose, Udp

4. Glucose, Uridine Diphosphate

5. Udp Glucose

6. Udpg

7. Uridine Diphosphate Glucose

8. Uridine Diphosphoglucose

2.3.2 Depositor-Supplied Synonyms

1. Udp-glucose

2. Uridine Diphosphate Glucose

3. Udpg

4. 133-89-1

5. Udp-alpha-d-glucose

6. Co-waldenase

7. Udpglucose

8. Co-galactoisomerase

9. Udp-a-d-glucose

10. Udp-d-glucose

11. Udp-glc

12. Uridine Diphosphoglucose

13. Cogalactoisomerase

14. 5'-diphosphoglucose

15. Uridine-5'-diphosphoglucose

16. Uridine Diphosphate-glucose

17. Uridine Diphospho-d-glucose

18. Uridine Pyrophosphate-glucose

19. Uridine 5'-diphosphoglucose

20. Uridine 5'-diphosphate Glucose

21. V50k1d7p4y

22. [[(2r,3s,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] Hydrogen Phosphate

23. Chebi:46229

24. Uridine 5'-diphospho-alpha-d-glucose

25. Uridine 5'-pyrophosphate Glucose Ester

26. Glucose-uridine-c1,5'-diphosphate

27. Uridine 5'-(trihydrogen Diphosphate), Mono-alpha-d-glucopyranosyl Ester

28. Udp Glucose

29. Uridine 5'-(trihydrogen Diphosphate), P'-alpha-d-glucopyranosyl Ester

30. Uridine 5'-diphospho-d-glucose

31. Unii-v50k1d7p4y

32. (udp)glucose

33. Udp-delta-glucose

34. (upd)-glucose

35. Einecs 205-121-4

36. Uridindiphosphoglucose

37. Mono-d-glucosyl Ester

38. Udp-alpha-delta-glucose

39. 5''''-diphosphoglucose

40. Schembl454078

41. Uridine Diphospho-delta-glucose

42. Chembl375951

43. Gtpl1783

44. Uridine-5''''-diphosphoglucose

45. Dtxsid00157902

46. Uridine 5'-diphospho-a-d-glucose

47. Cogalactoisomerase [who-dd]

48. Uridine-5'-monophosphate Glucopyranosyl-monophosphate Ester

49. Zinc8215472

50. Uridine 5-(trihydrogen Diphosphate)

51. Bdbm50209659

52. Bdbm50423218

53. Db01861

54. Uridine Diphosphate Glucose [mi]

55. Uridine 5'-diphospho-alpha-delta-glucose

56. Uridine Diphosphate Glucose [who-dd]

57. C00029

58. Q424649

59. Uridine 5'-(alpha-d-glucopyranosyl Pyrophosphate)

60. Uridine 5'-pyrophosphate A-d-glucopyranosyl Ester

61. Uridine 5'-pyrophosphate A-delta-glucopyranosyl Ester

62. Uridine 5''-[3-alpha-d-glucopyranosyl Dihydrogen Diphosphate]

63. Uridine 5'-(trihydrogen Pyrophosphate), Mono-d-glucosyl Ester

64. Uridine 5'-[3-alpha-d-glucopyranosyl Dihydrogen Diphosphate]

65. Uridine 5'-(trihydrogen Diphosphate) Alpha-d-gucopyranosyl Ester

66. Uridine 5'-pyrophosphate, Alpha-d-glucopyranosyl Ester (6ci,7ci)

67. Uridine 5'-(trihydrogen Diphosphate), P'-a-d-glucopyranosyl Ester (9ci)

68. Uridine 5/'-(trihydrogen Diphosphate), Mono-alpha-d-glucopyranosyl Ester

69. Uridine 5'-(trihydrogen Diphosphate), P'-.alpha.-d- Glucopyranosyl Ester

70. Uridine 5'-(trihydrogen Diphosphate), P'-.alpha.-d-glucopyranosyl Ester

71. Uridine 5'-(trihydrogen Pyrophosphate), Mono-alpha-d-glucopyranosyl Ester (8ci)

72. [(2r,3s,4r,5r)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl Dihydrogen Diphosphate (non-preferred Name)

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₂₄N₂O₁₇P₂
Molecular Weight	566.30 g/mol
XLogP3	-6.3
Hydrogen Bond Donor Count	9
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	9
Exact Mass	566.05502130 g/mol
Monoisotopic Mass	566.05502130 g/mol
Topological Polar Surface Area	292 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	964
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1