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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 of NONACTIN

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

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

Sources: DOI: 10.1002/hlca.1955038061

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Ammonium secretion by Malpighian tubules of Drosophila melanogaster: application of a novel ammonium-selective microelectrode.
2013 Oct 15
Mitochondrial uncoupler exerts a synthetic lethal effect against β-catenin mutant tumor cells.
2017 Apr
Patents

Sample Use Guides

Mice: 100 mg/kg
Route of Administration: Intraperitoneal
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 GMT 2023
Edited
by admin
on Sat Dec 16 08:24:56 GMT 2023
Record UNII
TTP24WX8P7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NONACTIN
MI  
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
Created by admin on Sat Dec 16 08:24:56 GMT 2023 , Edited by admin on Sat Dec 16 08:24:56 GMT 2023
PRIMARY
WIKIPEDIA
Nonactin
Created by admin on Sat Dec 16 08:24:56 GMT 2023 , Edited by admin on Sat Dec 16 08:24:56 GMT 2023
PRIMARY
ECHA (EC/EINECS)
229-911-3
Created by admin on Sat Dec 16 08:24:56 GMT 2023 , Edited by admin on Sat Dec 16 08:24:56 GMT 2023
PRIMARY
NSC
56409
Created by admin on Sat Dec 16 08:24:56 GMT 2023 , Edited by admin on Sat Dec 16 08:24:56 GMT 2023
PRIMARY
CAS
6833-84-7
Created by admin on Sat Dec 16 08:24:56 GMT 2023 , Edited by admin on Sat Dec 16 08:24:56 GMT 2023
PRIMARY
PUBCHEM
72519
Created by admin on Sat Dec 16 08:24:56 GMT 2023 , Edited by admin on Sat Dec 16 08:24:56 GMT 2023
PRIMARY
MERCK INDEX
m8032
Created by admin on Sat Dec 16 08:24:56 GMT 2023 , Edited by admin on Sat Dec 16 08:24:56 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID10218477
Created by admin on Sat Dec 16 08:24:56 GMT 2023 , Edited by admin on Sat Dec 16 08:24:56 GMT 2023
PRIMARY
NSC
52141
Created by admin on Sat Dec 16 08:24:56 GMT 2023 , Edited by admin on Sat Dec 16 08:24:56 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE