CHEBI:156450 - thiolutin

ChEBI IDCHEBI:156450
ChEBI Namethiolutin
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antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively. It is a potent inhibitor of RNA polymerases, inhibits the angiogenesis of human umbilical vein endothelial cells, and also inhibits JAMM metalloproteases.
Last Modified16 September 2020
SubmitterMartin Larralde
DownloadsMolfile
FormulaC8H8N2O2S2
Net Charge0
Average Mass228.298
Monoisotopic Mass228.00272
SMILESCC(=O)Nc1c2sscc-2n(C)c1=O
InChIInChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)
InChIKeyMHMRAFONCSQAIA-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Saccharothrix algeriensis (ncbitaxon:173560) - PubMed (24723205) Strain: NRRL B-24137
Streptomyces kasugaensis (ncbitaxon:1946) - PubMed (2262169) Strain: IFO 13851
Roles Classification
Chemical Role:
chelator  A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.
Biological Roles:
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).
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
toxin  Poisonous substance produced by a biological organism such as a microbe, animal or plant.
protein synthesis inhibitor  A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
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.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
ChEBI Ontology
Outgoing Relation(s)
thiolutin (CHEBI:156450) has functional parent holomycin (CHEBI:156451)
thiolutin (CHEBI:156450) has role angiogenesis inhibitor (CHEBI:48422)
thiolutin (CHEBI:156450) has role antibacterial agent (CHEBI:33282)
thiolutin (CHEBI:156450) has role antifungal agent (CHEBI:35718)
thiolutin (CHEBI:156450) has role antineoplastic agent (CHEBI:35610)
thiolutin (CHEBI:156450) has role bacterial metabolite (CHEBI:76969)
thiolutin (CHEBI:156450) has role chelator (CHEBI:38161)
thiolutin (CHEBI:156450) has role EC 2.7.7.6 (RNA polymerase) inhibitor (CHEBI:37416)
thiolutin (CHEBI:156450) has role marine metabolite (CHEBI:76507)
thiolutin (CHEBI:156450) has role protein synthesis inhibitor (CHEBI:48001)
thiolutin (CHEBI:156450) has role toxin (CHEBI:27026)
thiolutin (CHEBI:156450) is a acetamides (CHEBI:22160)
thiolutin (CHEBI:156450) is a dithiolopyrrolone antibiotic (CHEBI:156449)
IUPAC Name 
N-(4-methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide
Synonyms  Source
6-acetamido-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-oneChemIDplus
acetopyrrothinChemIDplus
acetopyrrothineChemIDplus
N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)acetamideChemIDplus
N-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)acetamideChEBI
Manual XrefsDatabases
CPD-17934MetaCyc
FDB012539FooDB
HMDB0034228HMDB
ThiolutinWikipedia
Registry NumbersSources
Reaxys:209485Reaxys
CAS:87-11-6ChemIDplus
Citations