Ketcher 08032011502D 1   1.00000     0.00000     0

 25 29  0     0  0            999 V2000
    6.2722   -2.7895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9998    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
    8.2982    1.3583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9970   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9519    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
    6.7634    0.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9502   -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   -2.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7642    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
    7.7179    2.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2705   -2.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7095    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
    6.0222    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
    7.9295    3.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4082   -0.2183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032   -2.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2338    3.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1874    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 15  2  0     0  0
  2  6  1  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  2  0     0  0
  5  9  1  0     0  0
  5 10  1  0     0  0
  6  8  1  0     0  0
  6  9  2  0     0  0
  7 11  1  0     0  0
  7 15  1  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:131915

> <NAME>
deoxyviolacein

> <DEFINITION>
A member of the class of oxindoles resulting from 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 1H-indol-3-yl group, where the newly-formed double bond has E configuration.

> <STAR>
3

> <SYNONYM>
deoxyviolacein

> <IUPAC_NAME>
(3E)-3-[5-(1H-indol-3-yl)-2-oxo-1,2-dihydro-3H-pyrrol-3-ylidene]-1,3-dihydro-2H-indol-2-one

> <FORMULA>
C20H13N3O2

> <MASS>
327.343

> <MONOISOTOPIC_MASS>
327.10078

> <CHARGE>
0

> <SMILES>
O=C1NC(=C\C1=C1/C(=O)NC2=CC=CC=C12)C1=CNC2=CC=CC=C12

> <INCHI>
InChI=1S/C20H13N3O2/c24-19-13(18-12-6-2-4-8-16(12)22-20(18)25)9-17(23-19)14-10-21-15-7-3-1-5-11(14)15/h1-10,21H,(H,22,25)(H,23,24)/b18-13+

> <INCHIKEY>
OJUJNNKCVPCATE-QGOAFFKASA-N

> <REAXYS_REGISTRY_NUMBER>
10779335

> <KEGG_COMPOUND_ACCESSION>
C21133

> <METACYC_ACCESSION>
CPD-14318

> <AGRICOLA_CITATION>
IND44792024

> <PUBMED_CITATION>
21779844; 22187076; 22391969; 23994489; 24889673; 25592762; 26506462

$$$$