N-(4-nitrobenzyl)-3-(4-oxo-3,4-dihydroquinazolin-2-yl)propanamide

ID: ALA3092550

PubChem CID: 136264439

Max Phase: Preclinical

Molecular Formula: C18H16N4O4

Molecular Weight: 352.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCc1nc2ccccc2c(=O)[nH]1)NCc1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C18H16N4O4/c23-17(19-11-12-5-7-13(8-6-12)22(25)26)10-9-16-20-15-4-2-1-3-14(15)18(24)21-16/h1-8H,9-11H2,(H,19,23)(H,20,21,24)

Standard InChI Key:  DWDKPWGFDIMBAY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   11.7818   -1.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7807   -2.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4887   -3.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4869   -1.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1956   -1.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1989   -2.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9113   -3.0656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6249   -2.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6215   -1.8271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9045   -1.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9000   -0.5980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3337   -3.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0403   -2.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7491   -3.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4557   -2.6446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7513   -3.8723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1645   -3.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8711   -2.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5758   -3.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2819   -2.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2801   -1.8220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5663   -1.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8631   -1.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9850   -1.4069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9817   -0.5897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6944   -1.8126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 24 25  2  0
 24 26  1  0
 21 24  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3092550

   ---

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: 352.35

Molecular Weight (Monoisotopic): 352.1172

AlogP: 2.08

#Rotatable Bonds: 6

Polar Surface Area: 117.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.92

CX Basic pKa: 5.40

CX LogP: 1.68

CX LogD: 1.69

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.52

Np Likeness Score: -1.66

References

1. Lindgren AE, Karlberg T, Ekblad T, Spjut S, Thorsell AG, Andersson CD, Nhan TT, Hellsten V, Weigelt J, Linusson A, Schüler H, Elofsson M..  (2013)  Chemical probes to study ADP-ribosylation: synthesis and biochemical evaluation of inhibitors of the human ADP-ribosyltransferase ARTD3/PARP3.,  56  (23): [PMID:24188023] [10.1021/jm401394u]

Source

Source(1):

• Scientific Literature