holomycin (CHEBI:156451)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	holomycin

ChEBI ID	CHEBI:156451

Definition	A 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antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 5 and 6 have been replaced by oxo and acetamido groups, respectively.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.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Martin Larralde

Supplier Information

Download	Molfile XML SDF

Formula

C7H6N2O2S2

Net Charge

Average Mass

214.260

Monoisotopic Mass

213.98707

InChI

InChI=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)

InChIKey

HBUNPJGMNVQSBX-UHFFFAOYSA-N

SMILES

CC(=O)NC1=C2SSC=C2NC1=O

Metabolite of Species	Details
Saccharothrix algeriensis (NCBI:txid173560)	of strain NRRL B-24137 See: PubMed
Streptomyces clavuligerus (NCBI:txid1901)	See: PubMed
Streptomyces clavuligerus (NCBI:txid1901)	See: PubMed
Streptomyces sp. (NCBI:txid1931)	of strain DT-A37 See: PubMed
Photobacterium halotolerans (NCBI:txid265726)	of strain S2753 See: PubMed
Yersinia ruckeri ATCC 29473 (NCBI:txid527005)	See: PubMed
Streptomyces flavogriseus (NCBI:txid67299)	of strain NJ-4 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):	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 ) 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 ) 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 ) antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. (via antibiotic antifungal agent )

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	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	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	Sources
6-(acetylamino)-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one	ChEBI
6-acetamido-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one	ChemIDplus
N-(4,5-dihydro-5-oxo-1,2-dithiolo-[4,3-b]pyrrol-6-yl)acetamide	ChemIDplus
N-(5-oxo-4H-dithiolo[4,3-b]pyrrol-6-yl)acetamide	ChEBI
N-demethylthiolutin	ChemIDplus
N-{5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}acetamide	IUPAC

Last Modified

16 September 2020