(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编号: 923
• 分子式: C31H36N2O11
• 平均质量: 612.62434
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: 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
• 商标名: Albamix; Cardelmycin; Cathocin; Cathomycin; Inamycin; Novo-R; Robiocina; Sirbiocina; Spheromycin; Stilbiocina; Streptonivicin; Albamycin
• 别名: Novobiocina [INN-Spanish]; Novobiocine [INN-French]; Novobiocinum [INN-Latin]; NOV; Crystallinic Acid; Antibiotic Pa-93; Novobiocin

登记号

• CAS号: 303-81-1
• PubChem SID: 160964386; 46507250
• PubChem CID: 54675769; 9346
• ATC码: QJ01XX95
• CHEMBL: 36506
• Chemspider ID: 10226117
• DrugBank ID: DB01051
• KEGG ID: C05080
• 美国药典/FDA物质标识码: 17EC19951N
• 维基百科标题: Novobiocin

理论计算性质

JChem

• Acid pKa: 6.9646654
• 质子受体: 9
• 质子供体: 5
• LogD (pH = 5.5): 3.249165
• LogD (pH = 7.4): 2.6537719
• Log P: 3.263811
• 摩尔折射率: 158.2442 cm^3
• 极化性: 60.648663 Å^3
• 极化表面积: 196.1 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 3.07
• LOG S: -4.8
• 溶解度: 9.66e-03 g/l

分子性质

理化性质

• 溶解度: Insoluble
• 疏水性(logP): 4.1

药理学性质

• 给药途径: intravenous
• 生物利用度: negligible oral bioavailability
• 排泄: renal
• 半衰期: 6 hours
• 代谢: excreted unchanged

产品相关信息

• 分类: Rare Genuine Natural Compounds

详细说明

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

参考文献

• 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