CHEBI:131914 - violacein

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ChEBI Name violacein
ChEBI ID CHEBI:131914
Definition A member of the class of hydroxyindoles resulting from the formal oxidative coupling between the 3-position of 1,3-dihydro-2H-indol-2-one and the 3-position of 1,3-dihydro-2H-pyrrol-2-one, which is substituted at the 5 position by a 5-hydroxy-1H-indol-3-yl group, where the newly-formed double bond has E configuration. It is a purple chromobacterial pigment that has antibacterial, antifungal, antiprotozoan, and anticancer properties.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
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Formula C20H13N3O3
Net Charge 0
Average Mass 343.336
Monoisotopic Mass 343.09569
InChI InChI=1S/C20H13N3O3/c24-10-5-6-15-12(7-10)14(9-21-15)17-8-13(19(25)23-17)18-11-3-1-2-4-16(11)22-20(18)26/h1-9,21,24H,(H,22,26)(H,23,25)/b18-13+
InChIKey XAPNKXIRQFHCHN-QGOAFFKASA-N
SMILES O=C/1NC=2C(\C1=C/3\C=C(NC3=O)C=4C=5C(NC4)=CC=C(O)C5)=CC=CC2
Metabolite of Species Details
Chromobacterium violaceum (NCBI:txid536) See: PubMed
Roles Classification
Biological Role(s): apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing violacein (CHEBI:131914) has functional parent proviolacein (CHEBI:131916)
violacein (CHEBI:131914) has role antibacterial agent (CHEBI:33282)
violacein (CHEBI:131914) has role antifungal agent (CHEBI:35718)
violacein (CHEBI:131914) has role antineoplastic agent (CHEBI:35610)
violacein (CHEBI:131914) has role apoptosis inducer (CHEBI:68495)
violacein (CHEBI:131914) has role bacterial metabolite (CHEBI:76969)
violacein (CHEBI:131914) is a hydroxyindoles (CHEBI:84729)
violacein (CHEBI:131914) is a olefinic compound (CHEBI:78840)
violacein (CHEBI:131914) is a oxindoles (CHEBI:38459)
violacein (CHEBI:131914) is a pyrroles (CHEBI:26455)
IUPAC Name
(3E)-3-[5-(5-hydroxy-1H-indol-3-yl)-2-oxo-1,2-dihydro-3H-pyrrol-3-ylidene]-1,3-dihydro-2H-indol-2-one
Synonym Source
violacein UniProt
Manual Xrefs Databases
C21136 KEGG COMPOUND
VIOLACEIN MetaCyc
View more database links
Registry Numbers Types Sources
49923 Reaxys Registry Number Reaxys
548-54-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
21779844 PubMed citation SUBMITTER
25592762 PubMed citation Europe PMC
25652759 PubMed citation Europe PMC
26339614 PubMed citation Europe PMC
26428920 PubMed citation Europe PMC
26521020 PubMed citation Europe PMC
26916415 PubMed citation Europe PMC
Last Modified
12 July 2016