CHEBI:131916 - proviolacein

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ChEBI Name proviolacein
ChEBI ID CHEBI:131916
Definition A hydroxyindole that is 2H-pyrrol-2-one which is substituted at positions 3 and 5 by 1H-indol-3-yl and 5-hydroxy-1H-indol-3-yl groups, respectively. It is an intermediate in the biosynthesis of the purple chromobacterial pigment violacein from L-tryptophan.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
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Formula C20H13N3O2
Net Charge 0
Average Mass 327.337
Monoisotopic Mass 327.10078
InChI InChI=1S/C20H13N3O2/c24-11-5-6-18-13(7-11)16(10-22-18)19-8-14(20(25)23-19)15-9-21-17-4-2-1-3-12(15)17/h1-10,21-22,24H
InChIKey AEUPUFUMWGIQGG-UHFFFAOYSA-N
SMILES OC=1C=C2C(C3=NC(C(C=4C=5C(NC4)=CC=CC5)=C3)=O)=CNC2=CC1
Metabolite of Species Details
Chromobacterium violaceum (NCBI:txid536) See: PubMed
Roles Classification
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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ChEBI Ontology
Outgoing proviolacein (CHEBI:131916) has functional parent L-tryptophan (CHEBI:16828)
proviolacein (CHEBI:131916) has role bacterial metabolite (CHEBI:76969)
proviolacein (CHEBI:131916) is a hydroxyindoles (CHEBI:84729)
proviolacein (CHEBI:131916) is a pyrroles (CHEBI:26455)
Incoming deoxyviolacein (CHEBI:131915) has functional parent proviolacein (CHEBI:131916)
violacein (CHEBI:131914) has functional parent proviolacein (CHEBI:131916)
IUPAC Name
5-(5-hydroxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-2H-pyrrol-2-one
Synonym Source
proviolacein UniProt
Manual Xref Database
CPD-14321 MetaCyc
View more database links
Registry Number Type Source
7340743 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17176066 PubMed citation Europe PMC
21779844 PubMed citation SUBMITTER
25664787 PubMed citation Europe PMC
Last Modified
12 July 2016