5-((1-(4-chlorobenzoyl)-1H-indol-3-yl)methylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione

ID: ALA511397

PubChem CID: 44574116

Max Phase: Preclinical

Molecular Formula: C22H16ClN3O4

Molecular Weight: 421.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)C(=Cc2cn(C(=O)c3ccc(Cl)cc3)c3ccccc23)C(=O)N(C)C1=O

Standard InChI:  InChI=1S/C22H16ClN3O4/c1-24-20(28)17(21(29)25(2)22(24)30)11-14-12-26(18-6-4-3-5-16(14)18)19(27)13-7-9-15(23)10-8-13/h3-12H,1-2H3

Standard InChI Key:  SYQNVQVOMHJJBW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    1.9827  -15.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9815  -16.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6943  -16.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6924  -15.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4105  -15.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4110  -16.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2020  -16.6608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6904  -15.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2012  -15.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4554  -14.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623  -14.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8187  -14.9739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6224  -14.8045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8810  -14.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3294  -13.4062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5194  -13.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5641  -15.7586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6884  -13.8518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9694  -12.9604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1725  -15.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5864  -12.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4573  -17.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9057  -18.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006  -17.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5494  -18.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8045  -19.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6163  -19.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1641  -18.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2644  -17.6161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2537  -19.8959    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  6  7  1  0
 12 17  2  0
  7  8  1  0
 14 18  2  0
  8  9  2  0
 16 19  2  0
  9  5  1  0
 13 20  1  0
  4  1  1  0
 15 21  1  0
  9 10  1  0
  7 22  1  0
  5  6  1  0
 22 23  1  0
 10 11  2  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
 25 26  2  0
  2  3  1  0
 26 27  1  0
  3  6  2  0
 27 28  2  0
 28 23  1  0
  1  2  2  0
 22 29  2  0
  5  4  2  0
 26 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA511397

   5-[[1-(4-Chlorobenzoyl)indol-3-yl]methylidene]-1,3-dimethyl-1,3-diazinane-2,4,6-trione

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 421.84

Molecular Weight (Monoisotopic): 421.0829

AlogP: 3.42

#Rotatable Bonds: 2

Polar Surface Area: 79.69

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.11

CX LogD: 3.11

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.47

Np Likeness Score: -1.23

References

1. Singh P, Kaur M, Verma P..  (2009)  Design, synthesis and anticancer activities of hybrids of indole and barbituric acids--identification of highly promising leads.,  19  (11): [PMID:19398334] [10.1016/j.bmcl.2009.04.014]

Source

Source(1):

• Scientific Literature