CHEBI:156452 - aureothricin

ChEBI IDCHEBI:156452
ChEBI Nameaureothricin
Stars
DefinitionA 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antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and propanoylamino groups, respectively.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.
Last Modified16 September 2020
SubmitterMartin Larralde
DownloadsMolfile
FormulaC9H10N2O2S2
Net Charge0
Average Mass242.325
Monoisotopic Mass242.01837
SMILESCCC(=O)Nc1c2sscc-2n(C)c1=O
InChIInChI=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)
InChIKeyUGZYFXMSMFMTSM-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Saccharothrix algeriensis (ncbitaxon:173560) - PubMed (20507156) Strain: NRRL B-24137
Streptomyces kasugaensis (ncbitaxon:1946) - PubMed (2262169)
Streptomyces sp. (ncbitaxon:1931) - DOI (10.7883/yoken1948.1.512) The species in which the compound was identified in is related to Nocardia farcinica. Strain: 26A
Streptomyces thioluteus (ncbitaxon:66431)
- PubMed (13096448)
- PubMed (27018252) Strain: DSM 40027
- Article (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.) Strain: G15
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
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).
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
ChEBI Ontology
Outgoing Relation(s)
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  Source
propionopyrrothineMetaCyc
N-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6- yl}propanamideIUPAC
N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)propionamideChEBI
4-methyl-6-propionamido-1,2-dithiolo[4,3-b]pyrrol-5(4H)-oneChEBI
propanoyl-pyrrothineMetaCyc
Manual XrefsDatabases
CPD-17938MetaCyc
C00018653KNApSAcK
Registry NumbersSources
CAS:574-95-8ChemIDplus
Citations