CHEBI:144088 - bromotopsentin

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ChEBI Name bromotopsentin
ChEBI ID CHEBI:144088
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Keeva Cochrane
Supplier Information
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Formula C20H13BrN4O2
Net Charge 0
Average Mass 421.254
Monoisotopic Mass 420.02219
InChI InChI=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)
InChIKey YHGQVXFIJGWOFP-UHFFFAOYSA-N
SMILES C=1(NC(=NC1)C(=O)C=2C=3C=CC(=CC3NC2)O)C=4C=5C=CC(=CC5NC4)Br
Metabolite of Species Details
Halichondriidae (NCBI:txid6060) See: J. Org. Chem.1988, v53(23), 5446-5453
Topsentia genitrix (WORMS:157419) See: Can. J. Chem, 1987, V68, 2118
Roles Classification
Biological Role(s): 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.
(via alkaloid )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 2 ChemIDplus
Manual Xrefs Databases
183528 Pubchem accession
C00026969 KNApSAcK
View more database links
Registry Number Type Source
112515-44-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16236327 PubMed citation Europe PMC
22030393 PubMed citation Europe PMC
25490431 PubMed citation Europe PMC
27933985 PubMed citation Europe PMC
Last Modified
17 July 2019