bromodeoxytopsentin (CHEBI:144087)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	bromodeoxytopsentin

ChEBI ID	CHEBI:144087

Definition	An 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.

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

Submitter	Keeva Cochrane

Supplier Information

Download	Molfile XML SDF

more structures >>

Formula

C20H13BrN4O

Net Charge

Average Mass

405.255

Monoisotopic Mass

404.02727

InChI

InChI=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)

InChIKey

RMAWSNVDVKZXDX-UHFFFAOYSA-N

SMILES

O=C(C1=CNC2=C1C=CC=C2)C3=NC(C4=CNC5=CC(Br)=CC=C54)=CN3

Metabolite of Species	Details
Topsentia pachastrelloides (NCBI:txid279594)	See: PubMed
Spongosorites genitrix (NCBI:txid6071)	See: PubMed

Roles Classification
Biological Role(s):	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. 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). metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

ChEBI Ontology
Outgoing	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

Registry Number	Type	Source
180633-55-0	CAS Registry Number	KNApSAcK

Last Modified

20 August 2019