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CHEBI:131914 - violacein

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:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
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.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
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
VIOLACEINMetaCyc
C21136KEGG COMPOUND
Registry NumbersSources
Reaxys:49923Reaxys
CAS:548-54-9ChemIDplus
Citations