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violacein

Go to external page http://purl.obolibrary.org/obo/CHEBI_131914

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.

Term info

Label

violacein

Synonyms
  • (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
  • violacein
database cross reference
Subsets

3_STAR

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 [ IUPAC ]

charge

0

formula

C20H13N3O3

has obo namespace

chebi_ontology

id

CHEBI:131914

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

mass

343.336

monoisotopicmass

343.09569

smiles

O=C/1NC=2C(\C1=C/3\C=C(NC3=O)C=4C=5C(NC4)=CC=C(O)C5)=CC=CC2