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-en-1-yl)benzamido]-8-methyl-2-oxo-2H-chromen-4-olate

• ChemBase ID: 106179
• Molecular Formular: C31H35N2NaO11
• Molecular Mass: 634.60617
• Monoisotopic Mass: 634.21385423
• SMILES: Cc1c(ccc2c1oc(=O)c(c2[O-])NC(=O)c1cc(c(cc1)O)CC=C(C)C)O[C@H]1[C@@H]([C@@H]([C@H](C(O1)(C)C)OC)OC(=O)N)O.[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(c2[O-])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 7-{[(2R,3R,4S,5R)-4-(carbamoyloxy)-3-hydroxy-5-methoxy-6,6-dimethyloxan-2-yl]oxy}-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamido]-8-methyl-2-oxo-2H-chromen-4-olate
• IUPAC Traditional 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-en-1-yl)benzamido]-8-methyl-2-oxochromen-4-olate
• Synonyms: N-[7-[[3-O-(Aminocarbonyl)-6-deoxy-5-C-methyl-4-O-methyl-α-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl]-4-hydroxy-3-(3-methyl-2-butenyl)benzamide monosodium salt; Albamycin Sodium; Cathomycin Sodium; Cathomycin Sodium Lyovac; NSC 2382; Vulcamycin; Novobiocin Sodium Salt; NOVOBIOCIN, SODIUM SALT, U.S.P.; Novobiocin sodium; 新生霉素 钠盐; 新生霉素 钠

Database IDs

• CAS Number: 1476-53-5
• EC Number: 216-023-6
• Beilstein Number: 3892910
• PubChem SID: 24897774; 162092977
• PubChem CID: 23663939

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: 60.37575 Å^3
• Polar Surface Area: 198.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: RD5425000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36-43
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H319
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Grade: USP
• Salt Data: Na+
• Suitability: meets USP testing specifications
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - N6160

Application
For the production of positively supercoiled plasmid DNA.1 Inhibitor of bacterial DNA gyrase and eukaryotic DNA topoisomerase.2 Inhibitor of retrovirus RNA-dependent DNA-polymerase.3
Biochem/physiol Actions
Mode of Action: Inhibits DNA synthesis by inhibiting the enzyme Topoisomerase II.Antimicrobial spectrum: Gram-positive bacterial.

Toronto Research Chemicals - N888500

Novobiocin is an antibiotic that acts as an inhibitor of bacterial DNA gyrase and eukaryotic DNA topoisomerase. Studies show that Novobiocin is also an inhibitor of retrovirus RNA-dependent DNA-polymerase. Novobiocin is used in the production of positivel

REFERENCES

• Cozarelli, N.R.: Science, 207, 953 (1980)
• Sumiyoshi, Y. et al.: J. Gen. Virol., 64, 2329 (1980)
• Lockshon, G. et al.: Nucleic Acids Res., 11, 2999 (1980)