(S)-3-(7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-N-(2-hydroxy-1-phenylethyl)propanamide

ID: ALA3092556

PubChem CID: 136245294

Max Phase: Preclinical

Molecular Formula: C19H18ClN3O3

Molecular Weight: 371.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCc1nc2cc(Cl)ccc2c(=O)[nH]1)N[C@H](CO)c1ccccc1

Standard InChI:  InChI=1S/C19H18ClN3O3/c20-13-6-7-14-15(10-13)21-17(23-19(14)26)8-9-18(25)22-16(11-24)12-4-2-1-3-5-12/h1-7,10,16,24H,8-9,11H2,(H,22,25)(H,21,23,26)/t16-/m1/s1

Standard InChI Key:  BGUNDSQBAHKEDB-MRXNPFEDSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   12.7930  -10.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7918  -11.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4999  -11.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4981  -10.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2067  -10.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2101  -11.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9225  -11.7988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6360  -11.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6327  -10.5603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9157  -10.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9112   -9.3312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3449  -11.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0515  -11.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7603  -11.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4669  -11.3778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7625  -12.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1757  -11.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8823  -11.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5870  -11.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2931  -11.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2913  -10.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5775  -10.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8743  -10.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1779  -12.6017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8867  -13.0084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0838  -11.7974    0.0000 Cl  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
 17 24  1  1
 24 25  1  0
  2 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3092556

   ---

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: 371.82

Molecular Weight (Monoisotopic): 371.1037

AlogP: 2.36

#Rotatable Bonds: 6

Polar Surface Area: 95.08

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.91

CX Basic pKa: 4.52

CX LogP: 1.71

CX LogD: 1.71

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.62

Np Likeness Score: -1.25

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