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CHEBI:144087 - bromodeoxytopsentin

Default Structure
ChEBI IDCHEBI:144087
ChEBI Namebromodeoxytopsentin
Stars
DefinitionAn aromatic ketone that is imidazole which is substituted by a 1H-indole-3-carbonyl group and a 6-bromo-1H-indol-3-yl group at positions 2 and 4, respectively. Isolated from the Mediterranean shallow-water sponge, Topsentia genetrix. It is a potent inhibitor of MRSA pyruvate kinase and exhibits antibacterial properties.
Last Modified20 August 2019
SubmitterKeeva
DownloadsMolfile
FormulaC20H13BrN4O
Net Charge0
Average Mass405.255
Monoisotopic Mass404.02727
SMILESO=C(c1ncc(-c2cnc3cc(Br)ccc23)n1)c1cnc2ccccc12
InChIInChI=1S/C20H13BrN4O/c21-11-5-6-13-14(8-23-17(13)7-11)18-10-24-20(25-18)19(26)15-9-22-16-4-2-1-3-12(15)16/h1-10,22-23H,(H,24,25)
InChIKeyRMAWSNVDVKZXDX-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Spongosorites genitrix (ncbitaxon:6071) - PubMed (10217734)
Topsentia pachastrelloides (ncbitaxon:279594) - PubMed (22030393)
Roles Classification
Biological Roles:
EC 2.7.1.40 (pyruvate kinase) inhibitor  An EC 2.7.1.* (phosphotransferases with an alcohol group as acceptor) inhibitor that interferes with the action of pyruvate kinase (EC 2.7.1.40).
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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
bromodeoxytopsentin (CHEBI:144087) has role antibacterial agent (CHEBI:33282)
bromodeoxytopsentin (CHEBI:144087) has role EC 2.7.1.40 (pyruvate kinase) inhibitor (CHEBI:143909)
bromodeoxytopsentin (CHEBI:144087) has role marine metabolite (CHEBI:76507)
bromodeoxytopsentin (CHEBI:144087) is a aromatic ketone (CHEBI:76224)
bromodeoxytopsentin (CHEBI:144087) is a bromoindole (CHEBI:52514)
bromodeoxytopsentin (CHEBI:144087) is a imidazoles (CHEBI:24780)
bromodeoxytopsentin (CHEBI:144087) is a indole alkaloid (CHEBI:38958)
IUPAC Names 
[4-(6-bromo-1H-indol-3-yl)-1H-imidazol-2-yl](1H-indol-3-yl)methanone
[5-(6-bromo-1H-indol-3-yl)-1H-imidazol-2-yl](1H-indol-3-yl)methanone
Manual XrefsDatabases
C00026966KNApSAcK
Registry NumbersSources
CAS:180633-55-0KNApSAcK
Citations