Ketcher 08032011512D 1   1.00000     0.00000     0

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M  END
> <ID>
CHEBI:131914

> <NAME>
violacein

> <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.

> <STAR>
3

> <SYNONYM>
violacein

> <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

> <FORMULA>
C20H13N3O3

> <MASS>
343.342

> <MONOISOTOPIC_MASS>
343.09569

> <CHARGE>
0

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

> <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

> <CAS_REGISTRY_NUMBER>
548-54-9

> <REAXYS_REGISTRY_NUMBER>
49923

> <CHEMIDPLUS>
548-54-9

> <KEGG_COMPOUND_ACCESSION>
C21136

> <METACYC_ACCESSION>
VIOLACEIN

> <PUBMED_CITATION>
21779844; 25592762; 25652759; 26339614; 26428920; 26521020; 26916415

$$$$