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

• ChemBase ID: 923
• Molecular Formular: C31H36N2O11
• Molecular Mass: 612.62434
• Monoisotopic Mass: 612.23190998
• SMILES: c12c(c(c(c(=O)o2)NC(=O)c2cc(c(cc2)O)CC=C(C)C)O)ccc(c1C)O[C@H]1[C@@H]([C@@H]([C@H](C(O1)(C)C)OC)OC(=O)N)O
• 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
• InChI: InChI=1S/C31H36N2O11/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)/t23-,25+,26-,29-/m1/s1
• InChIKey: YJQPYGGHQPGBLI-KGSXXDOSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5R,6R)-5-hydroxy-6-({4-hydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamido]-8-methyl-2-oxo-2H-chromen-7-yl}oxy)-3-methoxy-2,2-dimethyloxan-4-yl carbamate
• IUPAC Traditional name: novobiocin; (3R,4S,5R,6R)-5-hydroxy-6-({4-hydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamido]-8-methyl-2-oxochromen-7-yl}oxy)-3-methoxy-2,2-dimethyloxan-4-yl carbamate
• Brand Name: Albamix; Cardelmycin; Cathocin; Cathomycin; Inamycin; Novo-R; Robiocina; Sirbiocina; Spheromycin; Stilbiocina; Streptonivicin; Albamycin
• Synonyms: Novobiocina [INN-Spanish]; Novobiocine [INN-French]; Novobiocinum [INN-Latin]; NOV; Crystallinic Acid; Antibiotic Pa-93; Novobiocin

Database IDs

• CAS Number: 303-81-1
• PubChem SID: 160964386; 46507250
• PubChem CID: 9346; 54675769
• ATC CODE: QJ01XX95
• CHEMBL: 36506
• Chemspider ID: 10226117
• DrugBank ID: DB01051
• KEGG ID: C05080
• Unique Ingredient Identifier: 17EC19951N
• Wikipedia Title: Novobiocin

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.9646654
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 3.249165
• LogD (pH = 7.4): 2.6537719
• Log P: 3.263811
• Molar Refractivity: 158.2442 cm^3
• Polarizability: 60.648663 Å^3
• Polar Surface Area: 196.1 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.07
• LOG S: -4.8
• Solubility (Water): 9.66e-03 g/l

PROPERTIES

Physical Property

• Solubility: Insoluble
• Hydrophobicity(logP): 4.1

Pharmacology Properties

• Admin Routes: intravenous
• Bioavailability: negligible oral bioavailability
• Excretion: renal
• Half Life: 6 hours
• Metabolism: excreted unchanged

Product Information

• Classification: Rare Genuine Natural Compounds

DETAILS

DrugBank - DB01051

• Drug Groups: approved
• Description: 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) [PubChem]
• Indication: For the treatment of infections due to staphylococci and other susceptible organisms
• Pharmacology: Novobiocin is an aminocoumarin antibiotic that was produced by the actinomycete Streptomyces niveus. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. Other antibiotics in the aminocoumarin class include coumermycin A1 and clorobiocin.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Oral bioavailability is negligible.
• Half Life: 6 hours
• Protein Binding: 95%
• References: Vickers AA, Chopra I, O'neill AJ: Intrinsic novobiocin resistance in Staphylococcus saprophyticus. Antimicrob Agents Chemother. 2007 Sep 17;. [Pubmed] ; Burlison JA, Neckers L, Smith AB, Maxwell A, Blagg BS: Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90. J Am Chem Soc. 2006 Dec 6;128(48):15529-36. [Pubmed] ; Singh G, Jayanarayan KG, Dey CS: Novobiocin induces apoptosis-like cell death in topoisomerase II over-expressing arsenite resistant Leishmania donovani. Mol Biochem Parasitol. 2005 May;141(1):57-69. [Pubmed] ; CORBIN EE, PRIGOT A: Novobiocin; absorption, diffusion, and excretion studies. Antibiot Annu. 1956-1957;:392-5. [Pubmed] ; DAVID NA, BURGNER PR: Clinical effectiveness and safety of novobiocin. Antibiotic Med Clin Ther. 1956 Apr;2(4):219-29. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Vickers AA, Chopra I, O'neill AJ: Intrinsic novobiocin resistance in Staphylococcus saprophyticus. Antimicrob Agents Chemother. 2007 Sep 17;. Pubmed
• Burlison JA, Neckers L, Smith AB, Maxwell A, Blagg BS: Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90. J Am Chem Soc. 2006 Dec 6;128(48):15529-36. Pubmed
• Singh G, Jayanarayan KG, Dey CS: Novobiocin induces apoptosis-like cell death in topoisomerase II over-expressing arsenite resistant Leishmania donovani. Mol Biochem Parasitol. 2005 May;141(1):57-69. Pubmed
• CORBIN EE, PRIGOT A: Novobiocin; absorption, diffusion, and excretion studies. Antibiot Annu. 1956-1957;:392-5. Pubmed
• DAVID NA, BURGNER PR: Clinical effectiveness and safety of novobiocin. Antibiotic Med Clin Ther. 1956 Apr;2(4):219-29. Pubmed