CAS 303-81-1|Sirbiocina|Novobiocinum [INN-Latin]|Cathocin|NOV|Spheromycin|Inamycin|Novo-R|Cathomycin|Novobiocina [INN-Spanish]|Cardelmycin|Stilbiocina|Antibiotic Pa-93|(3R,4S,5R,6R)-5-hydroxy-6-({4-...

基本信息

化学结构

分子式

C₃₁H₃₆N₂O₁₁

分子量

612.62434

精确质量

612.23190998

电荷

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

Canonic 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

Isomeric 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

计算属性

JChem

Acid pKa

6.9646654

质子受体

质子供体

LogD (pH = 5.5)

3.249165

LogD (pH = 7.4)

2.6537719

Log P

3.263811

摩尔折射率

158.2442

极化性

60.648663

极化表面积

196.1

可自由旋转的化学键

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

数据来源

学术数据

产品目录

数据来源

名称和标识

商标名

SirbiocinaCathocinSpheromycinInamycinNovo-RCathomycinCardelmycinStilbiocinaRobiocinaAlbamixAlbamycinStreptonivicin

别名

Novobiocinum [INN-Latin]NOVNovobiocina [INN-Spanish]Antibiotic Pa-93Novobiocine [INN-French]Crystallinic AcidNovobiocin

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

(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 novobiocin

名称和标识

数据登录号

PubChem CID

PubChem SID

CAS号

Chemspider ID

DrugBank ID

CHEMBL

ATC码

美国药典/FDA物质标识码

KEGG ID

维基百科标题

数据登录号

化合物性质

理化性质

溶解度

Insoluble

疏水性(logP)

4.1

药理学性质

半衰期

6 hours

生物利用度

negligible oral bioavailability

给药途径

intravenous

排泄

renal

代谢

excreted unchanged

产品相关信息

分类

Rare Genuine Natural Compounds

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

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]

Wikipedia

Novobiocin

描述信息

参考文献

PubChem文献

数据源提供

• 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

• Vickers AA, Chopra I, O'neill AJ: Intrinsic novobiocin resistance in Staphylococcus saprophyticus. Antimicrob Agents Chemother. 2007 Sep 17;. Pubmed

• DAVID NA, BURGNER PR: Clinical effectiveness and safety of novobiocin. Antibiotic Med Clin Ther. 1956 Apr;2(4):219-29. Pubmed

• CORBIN EE, PRIGOT A: Novobiocin; absorption, diffusion, and excretion studies. Antibiot Annu. 1956-1957;:392-5. Pubmed

参考文献

生物活性

PubChem BioAssay

生物活性

导航

基本信息

计算属性

• RDKit

• JChem

• ALOGPS 2.1