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CHEBI:131914 - violacein

Default Structure
ChEBI IDCHEBI:131914
ChEBI Nameviolacein
Stars
DefinitionA 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.
Last Modified3 August 2020
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC20H13N3O3
Net Charge0
Average Mass343.342
Monoisotopic Mass343.09569
SMILESO=C1NC(c2cnc3ccc(O)cc23)=C/C1=C1\C(=O)Nc2ccccc21
InChIInChI=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+
InChIKeyXAPNKXIRQFHCHN-QGOAFFKASA-N
Species of MetaboliteComponentSourceComments
Chromobacterium violaceum (ncbitaxon:536) - PubMed (17176066)
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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
UniProt Name  Source
violaceinUniProt
Manual XrefsDatabases
C21136KEGG COMPOUND
VIOLACEINMetaCyc
Registry NumbersSources
Reaxys:49923Reaxys
CAS:548-54-9ChemIDplus
Citations