violacein (CHEBI:131914)

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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

Download	Molfile XML SDF

Formula

C20H13N3O3

Net Charge

Average Mass

343.342

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

OC1=CC=C2NC=C(C3=C\C(C(=O)N3)=C3/C(=O)NC4=CC=CC=C34)C2=C1

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.

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

Last Modified

03 August 2020