5-((1-benzoyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione

ID: ALA466450

PubChem CID: 44574090

Max Phase: Preclinical

Molecular Formula: C20H13N3O4

Molecular Weight: 359.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)C(=Cc2cn(C(=O)c3ccccc3)c3ccccc23)C(=O)N1

Standard InChI:  InChI=1S/C20H13N3O4/c24-17-15(18(25)22-20(27)21-17)10-13-11-23(16-9-5-4-8-14(13)16)19(26)12-6-2-1-3-7-12/h1-11H,(H2,21,22,24,25,27)

Standard InChI Key:  OZFWSCCMUQLBRR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    9.2794   -7.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2781   -7.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9911   -8.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9891   -6.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7072   -7.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7078   -7.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4989   -8.1192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9872   -7.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4980   -6.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7524   -5.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5592   -5.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1158   -6.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9194   -6.2629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1781   -5.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6264   -4.8643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8163   -5.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8611   -7.2169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9855   -5.3101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2663   -4.4185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7543   -8.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2026   -9.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3975   -9.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8460   -9.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1012  -10.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9130  -10.9098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4609  -10.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5613   -9.0747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  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
  7 20  1  0
  4  1  1  0
 20 21  1  0
  9 10  1  0
 21 22  2  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
 26 21  1  0
  2  3  1  0
 20 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA466450

   5-[(1-Benzoylindol-3-yl)methylidene]-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: 359.34

Molecular Weight (Monoisotopic): 359.0906

AlogP: 2.08

#Rotatable Bonds: 2

Polar Surface Area: 97.27

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.83

CX Basic pKa: ┄

CX LogP: 2.06

CX LogD: 1.40

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.54

Np Likeness Score: -0.88

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