NONACTIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C40H64O12
Molecular Weight	736.929
Optical Activity	UNSPECIFIED
Defined Stereocenters	16 / 16
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@@]([H])(O1)[C@@H](C)C(=O)O[C@H](C)C[C@@]3([H])CC[C@]([H])(O3)[C@H](C)C(=O)O[C@@H](C)C[C@]4([H])CC[C@@]([H])(O4)[C@@H](C)C(=O)O[C@H](C)C[C@@]5([H])CC[C@]([H])(O5)[C@H](C)C(=O)O[C@@H](C)C2

InChI

InChIKey=RMIXHJPMNBXMBU-QIIXEHPYSA-N

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-

HIDE SMILES / InChI

Molecular Formula	C40H64O12
Molecular Weight	736.929
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	16 / 16
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19902940 | https://www.ncbi.nlm.nih.gov/pubmed/4225380 | https://www.ncbi.nlm.nih.gov/pubmed/28107588 | https://www.ncbi.nlm.nih.gov/pubmed/7518390

Nonactin is the parent compound of macrotetrolides, a group of ionophore antibiotics produced by Streptomyces griseus. The antibacterial effects of nonactin depend upon its ability to form stable complexes with K+, Na+ or NH4 + ions and for it to support the passive diffusion of these ions across cell membranes. Nonactin has been shown to possess antitumor activity and to be an effective inhibitor of the P170-glycoprotein responsible for drug resistance in multiple drug-resistant cancer cell lines. Mitochondrial uncoupler nonactin induces apoptosis selectively in beta-catenin mutant tumor cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Apoptosis 155 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28107588	Activator 1430
oxidative phosphorylation 5 Target ID: GO:0006119 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4225380	Inhibitor 8297
Potassium ion 1 Target ID: Potassium ion Sources: https://www.ncbi.nlm.nih.gov/pubmed/19902940	Binding Agent 1064
Sodium ion 1 Target ID: Sodium ion Sources: https://www.ncbi.nlm.nih.gov/pubmed/19902940	Binding Agent 1064
Ammonium ion 1 Target ID: Ammonium ion Sources: https://www.ncbi.nlm.nih.gov/pubmed/19902940	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7518390 https://www.ncbi.nlm.nih.gov/pubmed/28107588	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ammonium secretion by Malpighian tubules of Drosophila melanogaster: application of a novel ammonium-selective microelectrode.	2013 Oct 15	23821719
nonG, a constituent of the nonactin biosynthetic gene cluster, regulates nocardamine synthesis in Streptomyces albus J1074.	2017 Aug 26	28634080

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 100 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

The expression levels of cleaved-PARP increased upon treatment with nonactin concentrations above 0.1 uM in four b-catenin mutant tumor cell lines, but nonactin did not induce PARP-cleavage in tumor cells expressing wild type b-catenin (including APC mutant tumor cells) at concentrations of up to 1 uM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:24:56 UTC 2023` Edited by `admin` on `Sat Dec 16 08:24:56 UTC 2023`
Record UNII	TTP24WX8P7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NONACTIN

Common Name

English

NONACTIN [MI]

Common Name

English

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)-

Systematic Name

English

NSC-52141

Code

English

NSC-56409

Code

English

Code System Code Type Description

FDA UNII

TTP24WX8P7