Ketcher 06011615182D 1   1.00000     0.00000     0

 25 29  0     0  0            999 V2000
    5.4916    4.1859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9997    0.5893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6860   -3.5956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2981    1.3583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9969   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9518    0.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6860   -1.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7633    0.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9501   -0.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4098   -0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7381   -2.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7641    1.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7381   -3.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7178    2.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2704   -2.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7094    0.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8707   -1.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0221    2.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8707   -3.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9294    3.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4081   -0.2183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032   -2.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2337    3.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1873    3.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032   -3.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0     0  0
  2  6  2  0     0  0
  2 10  1  0     0  0
  3 13  1  0     0  0
  3 15  1  0     0  0
  4 14  1  0     0  0
  4 16  1  0     0  0
  5  7  1  0     0  0
  5  9  2  0     0  0
  5 10  1  0     0  0
  6  8  1  0     0  0
  6  9  1  0     0  0
  7 11  1  0     0  0
  7 15  2  0     0  0
  8 12  1  0     0  0
  8 16  2  0     0  0
 10 21  2  0     0  0
 11 13  1  0     0  0
 11 17  2  0     0  0
 12 14  1  0     0  0
 12 18  2  0     0  0
 13 19  2  0     0  0
 14 20  2  0     0  0
 17 22  1  0     0  0
 18 23  1  0     0  0
 19 25  1  0     0  0
 20 24  1  0     0  0
 22 25  2  0     0  0
 23 24  2  0     0  0
M  END
> <ID>
CHEBI:131916

> <NAME>
proviolacein

> <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.

> <STAR>
3

> <SYNONYM>
proviolacein

> <IUPAC_NAME>
5-(5-hydroxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-2H-pyrrol-2-one

> <FORMULA>
C20H13N3O2

> <MASS>
327.337

> <MONOISOTOPIC_MASS>
327.10078

> <CHARGE>
0

> <SMILES>
OC=1C=C2C(C3=NC(C(C=4C=5C(NC4)=CC=CC5)=C3)=O)=CNC2=CC1

> <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

> <REAXYS_REGISTRY_NUMBER>
7340743

> <METACYC_ACCESSION>
CPD-14321

> <PUBMED_CITATION>
17176066; 21779844; 25664787

$$$$