sodium 4-[(7-{[(2R,3R,4S,5R)-4-(carbamoyloxy)-3-hydroxy-5-methoxy-6,6-dimethyloxan-2-yl]oxy}-4-hydroxy-8-methyl-2-oxo-2H-chromen-3-yl)carbamoyl]-2-(3-methylbut-2-en-1-yl)benzen-1-olate

• ChemBase ID: 73042
• Molecular Formular: C31H35N2NaO11
• Molecular Mass: 634.60617
• Monoisotopic Mass: 634.21385423
• SMILES: [C@H]1([C@H]([C@H]([C@@H](OC1(C)C)Oc1ccc2c(c1C)oc(=O)c(c2O)NC(=O)c1ccc(c(c1)CC=C(C)C)[O-])O)OC(=O)N)OC.[Na+]
• Canonical SMILES: CO[C@@H]1[C@@H](OC(=O)N)[C@@H](O)[C@@H](OC1(C)C)Oc1ccc2c(c1C)oc(=O)c(c2O)NC(=O)c1ccc(c(c1)CC=C(C)C)[O-].[Na+]
• 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
• InChIKey: WWPRGAYLRGSOSU-RNROJPEYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 4-[(7-{[(2R,3R,4S,5R)-4-(carbamoyloxy)-3-hydroxy-5-methoxy-6,6-dimethyloxan-2-yl]oxy}-4-hydroxy-8-methyl-2-oxo-2H-chromen-3-yl)carbamoyl]-2-(3-methylbut-2-en-1-yl)benzen-1-olate
• IUPAC Traditional name: sodium 4-[(7-{[(2R,3R,4S,5R)-4-(carbamoyloxy)-3-hydroxy-5-methoxy-6,6-dimethyloxan-2-yl]oxy}-4-hydroxy-8-methyl-2-oxochromen-3-yl)carbamoyl]-2-(3-methylbut-2-en-1-yl)benzenolate
• Synonyms: Albamycin; Cathomycin; Novobiocin sodium

Database IDs

• CAS Number: 1476-53-5
• PubChem SID: 162037962
• PubChem CID: 54726514

CALCULATED PROPERTIES

• Acid pKa: 6.9646654
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 3.249165
• LogD (pH = 7.4): 2.6537719
• Log P: 3.263811
• Molar Refractivity: 168.7945 cm^3
• Polarizability: 60.387146 Å^3
• Polar Surface Area: 198.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: sodium salt

DETAILS

Selleck Chemicals - S2492

Research Area: Infection
Biological Activity:
Novobiocin(Albamycin) is a very potent bacterial DNA gyrase and human organic anion transporters with Ki of of 14.87 ± 0.40 µM for hOAT1, 4.77 ± 1.12 µM for hOAT3, and 90.50 ± 7.50 µM for hOAT4. [1] Novobiocin as well as the other aminocoumarin antibiotics act as competitive inhibitors of the ATPase reaction catalysed by GyrB. The potency of novobiocin is considerably higher than that of the fluoroquinolones that also target DNA gyrase, but at a different site on the enzyme. The GyrA subunit is involved in the DNA nicking and ligation activity. [2]

REFERENCES

• Duan P et al. Drug Metab Dispos. 2009 Jun;37(6)