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Nonactin

Nonactin structure

CAS No:
6833-84-7
Formula:
C40H64O12
Chemical Name:
Nonactin
Synonyms:
4,13,22,31,37,38,39,40-Octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone,2,5,11,14,20,23,29,32-octamethyl-,(1R,2R,5R,7R,10S,11S,14S,16S,19R,20R,23R,25R,28S,29S,32S,34S)-;Nonactin;4,13,22,31,37,38,39,40-Octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone,2,5,11,14,20,23,29,32-octamethyl-,[1R-(1R*,2R*,5R*,7R*,10S*,11S*,14S*,16S*,19R*,20R*,23R*,25R*,28S*,29S*,32S*,34S*)]-;4,13,22,31,37,38,39,40-Octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane,nonactin deriv.;(1R,2R,5R,7R,10S,11S,14S,16S,19R,20R,23R,25R,28S,29S,32S,34S)-2,5,11,14,20,23,29,32-Octamethyl-4,13,22,31,37,38,39,40-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone;[1R-(1R*,2R*,5R*,7R*,10S*,11S*,14S*,16S*,19R*,20R*,23R*,25R*,28S*,29S*,32S*,34S*)]-2,5,11,14,20,23,29,32-Octamethyl-4,13,22,31,37,38,39,40-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone;Ammonium ionophore I;NSC 52141;NSC 56409;1400-56-2;6945-66-0;26082-94-0
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Nonactin is a naturally occurring macrotetrolide antibiotic from Streptomyces griseus. Nonactin acts as an ionophore for monovalent cations, including K+, and NH4+[1]. Nonactin is able to uncouple the oxidative phosphorylation of mitochondria. Nonactin selectively induces apoptosis in cell lines harboring active mutant β-catenin[2]. Nonactin inhibits the surface expression of endogenous HSP60[3].

Nonactin is a macrotetrolide.

Nonactin Basic Attributes

Molecular Weight：

736.93

Exact Mass：

736.93

EC Number：

229-911-3

UNII：

TTP24WX8P7

NSC Number：

56409|52141

DSSTox ID：

DTXSID10218477

HScode：

29321900

Characteristics

PSA：

142

XLogP3：

6.02200

Appearance：

white to faint yellow

Density：

1.11-1.15 g/cm³

Melting Point：

147.5 °C

Boiling Point：

890.6ºC at 760 mmHg

Flash Point：

352.7ºC

Refractive Index：

1.452

Water Solubility：

chloroform: soluble10mg/mL

Storage Conditions：

2-8°C

Toxicity：

LD50 intravenous in mouse: 246mg/kg

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

safety instructions：

22-24/25

RTECS Number：

RH1685000

Marks：

Drug Information

MeSH Entry Terms：

AKD-1A

Nonactin Use and Manufacturing

Nonactin is the smallest member of the macrotetrolide complex produced by a range of Streptomyces species. Originally the name, nonactin, reflected the lack of biological activity. The literature is confusing in this respect, as virtually all sources of nonactin are contaminated with small amounts of the much more active monactin. The BioAustralis nonactin has been purified to remove traces of other biologically-active macrotetrolides. Like the other macrotetrolides, nonactin is a monovalent cation ionophore with high selectivity for ammonium and potassium.

Computed Properties

Molecular Weight:736.9
XLogP3:6.6
Hydrogen Bond Acceptor Count:12
Exact Mass:736.43977747
Monoisotopic Mass:736.43977747
Topological Polar Surface Area:142
Heavy Atom Count:52
Complexity:1040
Defined Atom Stereocenter Count:16
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes