AUREOTHRICIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H10N2O2S2
Molecular Weight	242.318
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(=O)NC1=C2SSC=C2N(C)C1=O

InChI

InChIKey=UGZYFXMSMFMTSM-UHFFFAOYSA-N

InChI=1S/C9H10N2O2S2/c1-3-6(12)10-7-8-5(4-14-15-8)11(2)9(7)13/h4H,3H2,1-2H3,(H,10,12)

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24835149

Aureothricin is the earliest reported Dithiolopyrrolone (DTP). It was first isolated in 1948 by Umezawa and co-workers as a yellow crystalline solid from Streptomyces strain no. 26A related to Nocardia farcinica (referred to as A. farcinicus in the original manuscript). Notably, the compound was characterized by potent antibiotic activity against E. coli and a strong UV absorption maximum at 388 nm, distinctive of the pyrrothine core. Aureothricin is a known inhibitor of RNA Polymerase.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA-directed RNA polymerase 11 Target ID: CHEMBL2364672 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4597739	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
[On a yellow crystalline antibiotic, identical with aureothricin isolated from a new species of streptomyces, 39a, and its taxonomic study].	1953 Apr	13084502
Chemical studies on antibiotic substances. IV. A crystalline toxic substance of Streptomyces thioluteus producing aureothricin.	1953 Jul	13096448
IDENTIFICATION BY X-RAY POWDER DIFFRACTION OF THIOLUTIN AND AUREOTHRICIN ISOLATED BY PAPER CHROMATOGRAPHY.	1963	14275485
Dithiolopyrrolones: biosynthesis, synthesis, and activity of a unique class of disulfide-containing antibiotics.	2014 Jul	24835149

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

AUREOTHRICIN

Common Name

English

5-METHYL-3-PROPIONAMIDOPYRROLIN-4-ONE(4,3-D)-1,2-DITHIOLE

Common Name

English

N-(4,5-DIHYDRO-4-METHYL-5-OXO-1,2-DITHIOLO(4,3-B)PYRROL-6-YL)PROPANAMIDE

Systematic Name

English

PROPIONOPYRROTHINE

Common Name

English

AUREOTHRICIN [MI]

Common Name

English

4-METHYL-6-PROPIONAMIDO-1,2-DITHIOLO(4,3-B)PYRROL-5(4H)-ONE

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID60205993