CHEBI:156451 - holomycin

ChEBI IDCHEBI:156451
ChEBI Nameholomycin
Stars
DefinitionA dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 5 and 6 have been replaced by oxo and acetamido groups, respectively. It is an inhibitor of DNA-dependent RNA polymerase, and exhibits antibacterial and antitumour properties.
Last Modified16 September 2020
SubmitterMartin Larralde
DownloadsMolfile
FormulaC7H6N2O2S2
Net Charge0
Average Mass214.271
Monoisotopic Mass213.98707
SMILESCC(=O)Nc1c2sscc-2nc1=O
InChIInChI=1S/C7H6N2O2S2/c1-3(10)8-5-6-4(2-12-13-6)9-7(5)11/h2H,1H3,(H,8,10)(H,9,11)
InChIKeyHBUNPJGMNVQSBX-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Streptomyces clavuligerus (ncbitaxon:1901)
- PubMed (468729)
- PubMed (21041678)
Yersinia ruckeri ATCC 29473 (ncbitaxon:527005) - PubMed (23572522)
Streptomyces flavogriseus (ncbitaxon:67299) - PubMed (28740758) Strain: NJ-4
Photobacterium halotolerans (ncbitaxon:265726) - PubMed (21339958) Strain: S2753
Saccharothrix algeriensis (ncbitaxon:173560) - PubMed (32642829) Strain: NRRL B-24137
Streptomyces sp. (ncbitaxon:1931) - PubMed (28627048) Strain: DT-A37
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).
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.
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:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
holomycin (CHEBI:156451) has role antibacterial agent (CHEBI:33282)
holomycin (CHEBI:156451) has role antineoplastic agent (CHEBI:35610)
holomycin (CHEBI:156451) has role bacterial metabolite (CHEBI:76969)
holomycin (CHEBI:156451) has role chelator (CHEBI:38161)
holomycin (CHEBI:156451) has role EC 2.7.7.6 (RNA polymerase) inhibitor (CHEBI:37416)
holomycin (CHEBI:156451) has role marine metabolite (CHEBI:76507)
holomycin (CHEBI:156451) is a acetamides (CHEBI:22160)
holomycin (CHEBI:156451) is a dithiolopyrrolone antibiotic (CHEBI:156449)
Incoming Relation(s)
thiolutin (CHEBI:156450) has functional parent holomycin (CHEBI:156451)
IUPAC Name 
N-(5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide
Synonyms  Source
N-demethylthiolutinChemIDplus
N-(5-oxo-4H-dithiolo[4,3-b]pyrrol-6-yl)acetamideChEBI
N-{5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}acetamideIUPAC
N-(4,5-dihydro-5-oxo-1,2-dithiolo-[4,3-b]pyrrol-6-yl)acetamideChemIDplus
6-acetamido-1,2-dithiolo[4,3-b]pyrrol-5(4H)-oneChemIDplus
6-(acetylamino)-1,2-dithiolo[4,3-b]pyrrol-5(4H)-oneChEBI
Manual XrefsDatabases
CPD-17940MetaCyc
Registry NumbersSources
Reaxys:188430Reaxys
CAS:488-04-0ChemIDplus
Citations