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CHEBI:144087 - bromodeoxytopsentin

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).
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
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