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Merck
CN

74155

Sigma-Aldrich

无活菌素

from Streptomyces sp., ≥97.0% (TLC)

别名:

铵离子载体

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关于此项目

经验公式（希尔记法）:
C40H64O12
化学文摘社编号:
6833-84-7
分子量:
736.93
Beilstein:
76434
EC 号:
229-911-3
UNSPSC代码:
51102829
PubChem化学物质编号:
24886652
NACRES:
NA.85

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生物来源

Streptomyces sp.

质量水平

200

方案

≥97.0% (TLC)

表单

powder

颜色

white to faint yellow

抗生素抗菌谱

Gram-positive bacteria

作用机制

DNA synthesis | interferes
cell membrane | interferes
enzyme | inhibits

储存温度

2-8°C

SMILES字符串

C[C@H]1C[C@@H]2CC[C@@H](O2)[C@@H](C)C(=O)O[C@H](C)C[C@H]3CC[C@H](O3)[C@H](C)C(=O)O[C@@H](C)C[C@@H]4CC[C@@H](O4)[C@@H](C)C(=O)O[C@H](C)C[C@H]5CC[C@H](O5)[C@H](C)C(=O)O1

InChI

1S/C40H64O12/c1-21-17-29-9-13-34(49-29)26(6)38(42)46-23(3)19-31-11-15-36(51-31)28(8)40(44)48-24(4)20-32-12-16-35(52-32)27(7)39(43)47-22(2)18-30-10-14-33(50-30)25(5)37(41)45-21/h21-36H,9-20H2,1-8H3/t21-,22+,23+,24-,25-,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,36-

InChI key

RMIXHJPMNBXMBU-QIIXEHPYSA-N

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一般描述

Chemical structure: macrolide
May contain the homologues monactin and dinactin

应用

Nonactin is used as a neutral lipid membrane soluble ammonium (and potassium) ionophore, as an uncoupler of oxidative phosphorylation, and to inhibit surface expression of certain heat shock proteins (HSP60) .

生化/生理作用

Nonactin is a macrotetrolide that forms complexes with alkali cations, such as potassium and sodium. Nonactin has been reported to inhibit the processing of cytoplasmic precursor proteins destined for the mitochondria. Nonactin is a uncoupler of oxidative phosphorylation .

包装

5 mg

其他说明

Keep container tightly closed in a dry and well-ventilated place. Store under inert gas.Moisturesensitive. Keep in a dry place.
Natural macrotetrolide

储存分类代码

13 - Non Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

法规信息

涉药品监管产品
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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
BCBR6659V
BCBP9183V
1431469V
1431469

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[Macrotetrolides].
W Keller-Schierlein et al.
Fortschritte der Chemie organischer Naturstoffe = Progress in the chemistry of organic natural products. Progres dans la chimie des substances organiques naturelles, 26, 161-189 (1968-01-01)
Total synthesis of nonactin.
Ju Y.L.; Byeang H.K.
Tetrahedron, 52, 571-571 (1996)
Brian R Kusche et al.
Journal of the American Chemical Society, 131(47), 17155-17165 (2009-11-12)
Nonactin is a polyketide antibiotic produced by Streptomyces griseus ETH A7796 and is an ionophore that is selective for K(+) ions. It is a cyclic tetraester generated from two monomers of (+)-nonactic acid and two of (-)-nonactic acid, arranged (+)-(-)-(+)-(-)
V Gh Shlyonsky et al.
Biochimica et biophysica acta, 1758(11), 1723-1731 (2006-10-31)
We describe the phenomenon of mechanoelectrical transduction in macroscopic lipid bilayer membranes modified by two cation-selective ionophores, valinomycin and nonactin. We found that bulging these membranes, while maintaining the membrane tension constant, produced a marked supralinear increase in specific carrier-mediated
Brian R Kusche et al.
Bioorganic & medicinal chemistry letters, 19(4), 1233-1235 (2009-01-27)
Nonactin, produced by Streptomyces griseus ETH A7796, is a macrotetrolide assembled from nonactic acid. It is an effective inhibitor of drug efflux in multidrug resistant erythroleukemia K562 cells at sub-toxic concentrations and has been shown to possess both antibacterial and
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