2-(4-(2,4-dichlorobenzyloxy)-3-methoxyphenyl)quinazolin-4(3H)-one

ID: ALA4085392

PubChem CID: 137048155

Max Phase: Preclinical

Molecular Formula: C22H16Cl2N2O3

Molecular Weight: 427.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(-c2nc3ccccc3c(=O)[nH]2)ccc1OCc1ccc(Cl)cc1Cl

Standard InChI:  InChI=1S/C22H16Cl2N2O3/c1-28-20-10-13(21-25-18-5-3-2-4-16(18)22(27)26-21)7-9-19(20)29-12-14-6-8-15(23)11-17(14)24/h2-11H,12H2,1H3,(H,25,26,27)

Standard InChI Key:  KALYAVAMJXDJRM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   18.2960  -20.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8180  -18.3357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5376  -17.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5611  -17.1277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8615  -16.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1420  -17.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4459  -16.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7264  -17.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7029  -17.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3989  -18.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1185  -17.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8829  -15.8829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9532  -17.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2336  -18.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2101  -19.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9062  -19.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6257  -19.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6492  -18.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3218  -19.6585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9950  -20.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9680  -21.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6632  -22.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3831  -21.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4033  -20.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7074  -20.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3682  -18.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3913  -17.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0797  -22.1847    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.2481  -22.1048    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  2 11  1  0
  6 11  2  0
  5 12  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
  3 14  1  0
 17 19  1  0
 19  1  1  0
  1 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 18 26  1  0
 26 27  1  0
 23 28  1  0
 21 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4085392

   ---

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: 427.29

Molecular Weight (Monoisotopic): 426.0538

AlogP: 5.48

#Rotatable Bonds: 5

Polar Surface Area: 64.21

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.11

CX Basic pKa: 4.07

CX LogP: 5.24

CX LogD: 5.18

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: -1.07

References

1. Mohd Siddique MU, McCann GJ, Sonawane VR, Horley N, Gatchie L, Joshi P, Bharate SB, Jayaprakash V, Sinha BN, Chaudhuri B..  (2017)  Quinazoline derivatives as selective CYP1B1 inhibitors.,  130  [PMID:28259840] [10.1016/j.ejmech.2017.02.032]

Source

Source(1):

• Scientific Literature