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Chemistry

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Also known as: Albamycin, Sodium novobiocin, Cathomycin, Albadry, Novobiocin, monosodium salt, Novobiocin monosodium salt

Molecular Formula

C₃₁H₃₅N₂NaO₁₁

Molecular Weight

634.6 g/mol

InChI Key

WWPRGAYLRGSOSU-RNROJPEYSA-M

FDA UNII

Q9S9NQ5YIY

An antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189)

1 2D Structure

Novobiocin Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;7-[(2R,3R,4S,5R)-4-carbamoyloxy-3-hydroxy-5-methoxy-6,6-dimethyloxan-2-yl]oxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-8-methyl-2-oxochromen-4-olate

2.1.2 InChI

InChI=1S/C31H36N2O11.Na/c1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29;/h7,9-13,23,25-26,29,34-36H,8H2,1-6H3,(H2,32,39)(H,33,37);/q;+1/p-1/t23-,25+,26-,29-;/m1./s1

2.1.3 InChI Key

WWPRGAYLRGSOSU-RNROJPEYSA-M

2.1.4 Canonical SMILES

CC1=C(C=CC2=C1OC(=O)C(=C2[O-])NC(=O)C3=CC(=C(C=C3)O)CC=C(C)C)OC4C(C(C(C(O4)(C)C)OC)OC(=O)N)O.[Na+]

2.1.5 Isomeric SMILES

CC1=C(C=CC2=C1OC(=O)C(=C2[O-])NC(=O)C3=CC(=C(C=C3)O)CC=C(C)C)O[C@H]4[C@@H]([C@@H]([C@H](C(O4)(C)C)OC)OC(=O)N)O.[Na+]

2.2 Other Identifiers

2.2.1 UNII

Q9S9NQ5YIY

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Calcium, Novobiocin

2. Crystallinic Acid

3. Monosodium Salt Novobiocin

4. Novobiocin

5. Novobiocin Calcium

6. Novobiocin, Monosodium Salt

7. Sodium, Novobiocin

8. Streptonivicin

2.3.2 Depositor-Supplied Synonyms

1. Albamycin

2. Sodium Novobiocin

3. Cathomycin

4. Albadry

5. Novobiocin, Monosodium Salt

6. Novobiocin Monosodium Salt

7. Q9s9nq5yiy

8. 1476-53-5

9. Cathomycin Sodium

10. Chebi:31924

11. Nsc-2382

12. Vulcamycin

13. Drygard/biodry

14. Sodium Albamycin

15. Dsstox_cid_3386

16. Monosodium Novobiocin

17. Novobiocin Monosodium

18. Dsstox_rid_77008

19. Dsstox_gsid_23386

20. Cardelmycin Sodium Salt

21. Pa 93 Na Salt

22. Streptonivicin Sodium Salt

23. Inabiocin

24. Novobiocin, Sodium Deriv.

25. Albamycinsodium

26. Novobiocin Natrium

27. Albamycin Capsules

28. Novobiocina Bomaca

29. Component Of Albamycin Capsules

30. Albamycin (capsule)

31. Antibiotic From Streptomyces Spheroides

32. Novobiocin Sodium [usp]

33. Unii-q9s9nq5yiy

34. Novobiocin Sodium Salt (van)

35. U 6591

36. U-6591

37. Albamycin (tn)

38. Nsc 2382

39. Einecs 216-023-6

40. S2492_selleck

41. Ncgc00017033-01

42. Cas-1476-53-5

43. Novobiocin Sodium (jan/usp)

44. Spectrum1500444

45. Novobiocin Sodium [jan]

46. Chembl3183453

47. Dtxsid9023386

48. Hms500m22

49. Novobiocin Sodium [vandf]

50. Novobiocin Sodium [mart.]

51. Hms1920d04

52. Hms2091l04

53. Novobiocin Sodium [who-dd]

54. Tox21_110747

55. Ccg-40336

56. Akos030503807

57. Novobiocin Sodium [green Book]

58. Tox21_110747_1

59. Novobiocin Sodium [usp Impurity]

60. Ncgc00178810-03

61. Novobiocin Sodium [usp Monograph]

62. Novobiocin Sodium, Albamycin, Cathomycin

63. D01209

64. N-9100

65. Novobiocin Sodium, Meets Usp Testing Specifications

66. Q27114724

67. Novobiocin Sodium Salt, Antibiotic For Culture Media Use Only

68. 7-(4-(carbamoyloxy)tetrahydro-3-hydroxy-5-methoxy-6,6-dimethylpyran-2-yloxy)-4-hydroxy-3-(4-hydroxy-3-(4-hydroxy-3-(3-methyl-2-butenyl)benzamido)-8-methylcoumarin Monosodium Salt

69. 7-[(2r,3r,4s,5r)-4-carbamoyloxy-3-hydroxy-5-methoxy-6,6-dimethyl-tetrahydropyran-2-yl]oxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-8-methyl-2-oxo-chromen-4-olate

70. Benzamide, N-(7-((3-o-(aminocarbonyl)-6-deoxy-5-c-methyl-4-o-methyl-.alpha.-l-lyxo-hexopyranosyl)oxy)-4-hydroxy-8-methyl-2-oxo-2h-1-benzopyran-3-yl)-4-hydroxy-3-(3-methyl-2-buten-1-yl)-, Sodium Salt (1:1)

71. Benzamide, N-(7-((3-o-(aminocarbonyl)-6-deoxy-5-c-methyl-4-o-methyl-.beta.-l-lyxo-hexopyranosyl)oxy)-4-hydroxy-8-methyl-2-oxo-2h-1-benzopyran-3-yl)-4-hydroxy-3-(3-methyl-2-butenyl-, Monosodium Salt

72. Benzamide, N-(7-((3-o-(aminocarbonyl)-6-deoxy-5-c-methyl-4-o-methyl-beta-l-lyxo-hexopyranosyl)oxy)-4-hydroxy-8-methyl-2-oxo-2h-1-benzopyran-3-yl)-4-hydroxy-3-(3-methyl-2-butenyl)-, Monosodium Salt

73. Benzamide, N-(7-((3-o-(aminocarbonyl)-6-deoxy-5-c-methyl-4-o-methyl-beta-l-lyxo-hexopyranosyl)oxy)-4-hydroxy-8-methyl-2-oxo-2h-1-benzopyran-3-yl)-4-hydroxy-3-(3-methyl-2-butenyl-, Monosodium Salt

74. Sodium 7-(((2r,3r,4s,5r)-4-(carbamoyloxy)-3-hydroxy-5-methoxy-6,6-dimethyltetrahydro-2h-pyran-2-yl)oxy)-3-(4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamido)-8-methyl-2-oxo-2h-chromen-4-olate

75. Sodium;7-[(2r,3r,4s,5r)-4-carbamoyloxy-3-hydroxy-5-methoxy-6,6-dimethyloxan-2-yl]oxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-8-methyl-2-oxochromen-4-olate

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₃₁H₃₅N₂NaO₁₁
Molecular Weight	634.6 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	9
Exact Mass	634.21385422 g/mol
Monoisotopic Mass	634.21385422 g/mol
Topological Polar Surface Area	199 Å²
Heavy Atom Count	45
Formal Charge	0
Complexity	1160
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	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial 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.)

Nucleic Acid Synthesis Inhibitors

Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)

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