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CHEBI:144088 - bromotopsentin

ChEBI IDCHEBI:144088
ChEBI Namebromotopsentin
Stars
DefinitionAn aromatic ketone that is imidazole that is substituted at positions 2 and 5 by (6-hydroxy-1H-indol-3-yl)carbonyl and 6-bromo-1H-indol-3-yl groups respectively. Isolated from Mediterranean shallow-water sponges Topsentia genetrix, and from Caribbean deep-sea sponges of the Halichondriidae family, it has antitumour and antiviral properties. Toxic to fish.
Last Modified17 July 2019
SubmitterKeeva
DownloadsMolfile
FormulaC20H13BrN4O2
Net Charge0
Average Mass421.254
Monoisotopic Mass420.02219
SMILESO=C(c1ncc(-c2cnc3cc(Br)ccc23)n1)c1cnc2cc(O)ccc12
InChIInChI=1S/C20H13BrN4O2/c21-10-1-3-12-14(7-22-16(12)5-10)18-9-24-20(25-18)19(27)15-8-23-17-6-11(26)2-4-13(15)17/h1-9,22-23,26H,(H,24,25)
InChIKeyYHGQVXFIJGWOFP-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Topsentia genitrix (WORMS:157419) - Article (Can. J. Chem, 1987, V68, 2118)
Halichondriidae (ncbitaxon:6060) - Article (J. Org. Chem.1988, v53(23), 5446-5453)
Roles Classification
Biological Roles:
antiviral agent  A substance that destroys or inhibits replication of viruses.
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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
bromotopsentin (CHEBI:144088) has role antineoplastic agent (CHEBI:35610)
bromotopsentin (CHEBI:144088) has role antiviral agent (CHEBI:22587)
bromotopsentin (CHEBI:144088) has role marine metabolite (CHEBI:76507)
bromotopsentin (CHEBI:144088) is a aromatic ketone (CHEBI:76224)
bromotopsentin (CHEBI:144088) is a bromoindole (CHEBI:52514)
bromotopsentin (CHEBI:144088) is a hydroxyindoles (CHEBI:84729)
bromotopsentin (CHEBI:144088) is a imidazoles (CHEBI:24780)
bromotopsentin (CHEBI:144088) is a indole alkaloid (CHEBI:38958)
IUPAC Name 
[4-(6-bromo-1H-indol-3-yl)-1H-imidazol-2-yl](6-hydroxy-1H-indol-3-yl)methanone
Synonym  Source
Topsentin B 2ChemIDplus
Manual XrefsDatabases
183528PubChem Compound
C00026969KNApSAcK
Registry NumbersSources
CAS:112515-44-3ChemIDplus
Citations