aureothricin (CHEBI:156452)

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ChEBI Name	aureothricin

ChEBI ID	CHEBI:156452

Definition	A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and propanoylamino groups, respectively. It is a moderate antimicrobial by-product of the thiolutin fermentation in various Streptomyces species.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Martin Larralde

Supplier Information

Download	Molfile XML SDF

Formula

C9H10N2O2S2

Net Charge

Average Mass

242.310

Monoisotopic Mass

242.01837

InChI

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)

InChIKey

UGZYFXMSMFMTSM-UHFFFAOYSA-N

SMILES

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

Metabolite of Species	Details
Saccharothrix algeriensis (NCBI:txid173560)	of strain NRRL B-24137 See: PubMed
Streptomyces sp. (NCBI:txid1931)	The species in which the compound was identified in is related to Nocardia farcinica. of strain 26A See: DOI
Streptomyces kasugaensis (NCBI:txid1946)	See: PubMed
Streptomyces thioluteus (NCBI:txid66431)	See: PubMed
Streptomyces thioluteus (NCBI:txid66431)	of strain DSM 40027 See: PubMed
Streptomyces thioluteus (NCBI:txid66431)	of strain G15 See: Hu, J, Lou, Z, Yu, Q, et al. (1995) Taxonomy of the strain G15 producing new isochromanequinone antibiotics. Zhongguo Kang Sheng su za zhi = Chinese Journal of Antibiotics, 20(4), 249-253.

Roles Classification
Biological Role(s):	bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. (via dithiolopyrrolone antibiotic ) antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria. (via dithiolopyrrolone antibiotic ) EC 2.7.7.6 (RNA polymerase) inhibitor An EC 2.7.7.* (nucleotidyltransferase) inhibitor that interferes with the action of RNA polymerase (EC 2.7.7.6). antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. (via alkaloid antibiotic ) metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid ) antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. (via antibiotic antifungal agent )

Application(s):	angiogenesis inhibitor An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.

ChEBI Ontology
Outgoing	aureothricin (CHEBI:156452) has role angiogenesis inhibitor (CHEBI:48422) aureothricin (CHEBI:156452) has role antibacterial agent (CHEBI:33282) aureothricin (CHEBI:156452) has role bacterial metabolite (CHEBI:76969) aureothricin (CHEBI:156452) has role EC 2.7.7.6 (RNA polymerase) inhibitor (CHEBI:37416) aureothricin (CHEBI:156452) is a dithiolopyrrolone antibiotic (CHEBI:156449) aureothricin (CHEBI:156452) is a secondary carboxamide (CHEBI:140325)

IUPAC Name

N-(4-methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)propanamide

Synonyms	Sources
4-methyl-6-propionamido-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one	ChEBI
N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)propionamide	ChEBI
N-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6- yl}propanamide	IUPAC
propanoyl-pyrrothine	MetaCyc
propionopyrrothine	MetaCyc

Registry Number	Type	Source
574-95-8	CAS Registry Number	ChemIDplus

Last Modified

16 September 2020