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N2286

Sigma-Aldrich

Nonactin

from Streptomyces griseus, ≥98.0% (Total homologs, HPLC)

Sinónimos:

Ammonium ionophore I, Ammonium ionophore

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About This Item

Fórmula empírica (notación de Hill):
C40H64O12
Número de CAS:
6833-84-7
Peso molecular:
736.93
Beilstein/REAXYS Number:
76434
EC Number:
229-911-3
UNSPSC Code:
51102829
PubChem Substance ID:
24897566
NACRES:
NA.76

biological source

Streptomyces griseus

Quality Level

300

description

Natural macrotetrolide, may contain homologues (like monactin and dinactin)

assay

≥98.0% (Total homologs, HPLC)

form

powder

solubility

chloroform: soluble 10 mg/mL

antibiotic activity spectrum

Gram-positive bacteria

mode of action

DNA synthesis | interferes
cell membrane | interferes

storage temp.

2-8°C

SMILES string

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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General description

Chemical structure: macrolide

Application

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 an uncoupler of oxidative phosphorylation .

Biochem/physiol Actions

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

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Pei-Ji Zhao et al.
Archives of pharmacal research, 28(11), 1228-1232 (2005-12-15)
Four compounds, including two novel macrolides, were isolated from an endophyte Streptomyces sp. Is9131 of Maytenus hookeri. Spectral data indicated that these compounds were dimeric dinactin (1), dimeric nonactin (2), cyclo-homononactic acid (3), and cyclo-nonactic acid (4). Bioassay results showed
Total synthesis of nonactin.
Ju Y.L.; Byeang H.K.
ChemInform, 52, 571-571 (1996)
Sarah B Luesse et al.
Bioorganic & medicinal chemistry letters, 18(14), 3946-3949 (2008-07-01)
The synthesis of a library of nonactic acid-derived triazoloamide derivatives and their evaluation as antimicrobial agents is described.
Sergey M Korotkov et al.
Journal of biochemical and molecular toxicology, 21(2), 81-91 (2007-04-12)
The effects of Tl(+) ions on isolated rat liver mitochondria were studied in the presence of nonactin, a cyclic ionophore. Nonenergized rat liver mitochondria were increasingly swollen at an elevated concentration of Tl(+) in the 160 mOsm medium containing 0-150
Joshua B Phillips et al.
Bioorganic & medicinal chemistry letters, 20(19), 5936-5938 (2010-08-31)
We have shown that the intentional engineering of a natural product biosynthesis pathway is a useful way to generate stereochemically complex scaffolds for use in the generation of combinatorial libraries that capture the structural features of both natural products and
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