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antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively.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
Streptomyces kasugaensis (ncbitaxon:1946) - PubMed (2262169) Strain: IFO 13851
Saccharothrix algeriensis (ncbitaxon:173560) - PubMed (24723205) Strain: NRRL B-24137
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:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of 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.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in 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).
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.
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:
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
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
N-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)acetamideChEBI
acetopyrrothineChemIDplus
acetopyrrothinChemIDplus
N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)acetamideChemIDplus
6-acetamido-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-oneChemIDplus
Manual XrefsDatabases
ThiolutinWikipedia
FDB012539FooDB
CPD-17934MetaCyc
HMDB0034228HMDB
Registry NumbersSources
Reaxys:209485Reaxys
CAS:87-11-6ChemIDplus
Citations