CHEBI:156450 - thiolutin

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ChEBI Name thiolutin
ChEBI ID CHEBI:156450
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antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively.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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Martin Larralde
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Formula C8H8N2O2S2
Net Charge 0
Average Mass 228.280
Monoisotopic Mass 228.00272
InChI InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)
InChIKey MHMRAFONCSQAIA-UHFFFAOYSA-N
SMILES CN1C(=O)C(NC(C)=O)=C2SSC=C12
Metabolite of Species Details
Saccharothrix algeriensis (NCBI:txid173560) of strain NRRL B-24137 See: PubMed
Streptomyces kasugaensis (NCBI:txid1946) of strain IFO 13851 See: PubMed
Roles Classification
Chemical Role(s): chelator
A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.
Biological Role(s): protein synthesis inhibitor
A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
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.
(via dithiolopyrrolone antibiotic )
toxin
Poisonous substance produced by a biological organism such as a microbe, animal or plant.
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.
(via dithiolopyrrolone antibiotic )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via antibiotic antifungal agent )
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 )
Application(s): 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.
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ChEBI Ontology
Outgoing 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 Sources
6-acetamido-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one ChemIDplus
acetopyrrothin ChemIDplus
acetopyrrothine ChemIDplus
N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)acetamide ChemIDplus
N-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)acetamide ChEBI
Manual Xrefs Databases
CPD-17934 MetaCyc
FDB012539 FooDB
HMDB0034228 HMDB
Thiolutin Wikipedia
View more database links
Registry Numbers Types Sources
209485 Reaxys Registry Number Reaxys
87-11-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
16 September 2020