2-(4-(4-fluorobenzyloxy)-3-methoxyphenyl)quinazolin-4(3H)-one

ID: ALA4103323

PubChem CID: 137657597

Max Phase: Preclinical

Molecular Formula: C22H17FN2O3

Molecular Weight: 376.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(-c2nc3ccccc3c(=O)[nH]2)ccc1OCc1ccc(F)cc1

Standard InChI:  InChI=1S/C22H17FN2O3/c1-27-20-12-15(21-24-18-5-3-2-4-17(18)22(26)25-21)8-11-19(20)28-13-14-6-9-16(23)10-7-14/h2-12H,13H2,1H3,(H,24,25,26)

Standard InChI Key:  HAFYFUAFMJQXCJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   22.3407  -20.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8627  -18.6493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5823  -18.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6058  -17.4414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9062  -17.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1867  -17.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4906  -16.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7711  -17.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7476  -18.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4436  -18.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1632  -18.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9276  -16.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9979  -18.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2783  -18.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2548  -19.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9509  -19.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6704  -19.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6939  -18.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3664  -19.9721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0397  -21.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0127  -22.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7079  -22.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4277  -22.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4480  -21.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7521  -20.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4129  -18.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4360  -17.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1243  -22.4984    0.0000 F   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
M  END

Alternative Forms

1. Parent:

   

   ALA4103323

   ---

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: 376.39

Molecular Weight (Monoisotopic): 376.1223

AlogP: 4.32

#Rotatable Bonds: 5

Polar Surface Area: 64.21

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.96

CX Basic pKa: 4.07

CX LogP: 4.18

CX LogD: 4.09

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: -0.96

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