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

ID: ALA511553

PubChem CID: 3114175

Max Phase: Preclinical

Molecular Formula: C22H19N3O3

Molecular Weight: 373.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)C(=Cc2cn(Cc3ccccc3)c3ccccc23)C(=O)N(C)C1=O

Standard InChI:  InChI=1S/C22H19N3O3/c1-23-20(26)18(21(27)24(2)22(23)28)12-16-14-25(13-15-8-4-3-5-9-15)19-11-7-6-10-17(16)19/h3-12,14H,13H2,1-2H3

Standard InChI Key:  VLNKFANNJDIHFV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   15.4622    0.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4608   -0.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1738   -0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1719    0.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8900    0.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8906   -0.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6816   -0.5982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1700    0.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6807    0.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9351    1.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7419    1.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2985    1.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1023    1.2581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3608    2.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8092    2.6568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9990    2.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0438    0.3041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1682    2.2109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4490    3.1026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6524    0.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0663    3.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9370   -1.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3853   -1.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5802   -1.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0288   -2.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2841   -3.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0958   -3.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6436   -2.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  5  4  2  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
M  END

Alternative Forms

1. Parent:

   

   ALA511553

   5-[(1-benzyl-1H-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: 373.41

Molecular Weight (Monoisotopic): 373.1426

AlogP: 3.12

#Rotatable Bonds: 3

Polar Surface Area: 62.62

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.28

CX LogD: 3.28

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -1.25

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]

2. Singh P, Kaur M, Holzer W..  (2010)  Synthesis and evaluation of indole, pyrazole, chromone and pyrimidine based conjugates for tumor growth inhibitory activities--development of highly efficacious cytotoxic agents.,  45  (11): [PMID:20810192] [10.1016/j.ejmech.2010.08.004]

Source

Source(1):

• Scientific Literature