rac-3-(1-(3-methoxyphenyl)-3-(methylamino)propyl)-6-(1H-pyrazol-4-yl)quinazolin-4(3H)-one

ID: ALA4753687

PubChem CID: 155594124

Max Phase: Preclinical

Molecular Formula: C22H23N5O2

Molecular Weight: 389.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNCCC(c1cccc(OC)c1)n1cnc2ccc(-c3cn[nH]c3)cc2c1=O

Standard InChI:  InChI=1S/C22H23N5O2/c1-23-9-8-21(16-4-3-5-18(10-16)29-2)27-14-24-20-7-6-15(11-19(20)22(27)28)17-12-25-26-13-17/h3-7,10-14,21,23H,8-9H2,1-2H3,(H,25,26)

Standard InChI Key:  GGOKZYYLQABONW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   23.8797  -14.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8835  -15.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6006  -16.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5891  -14.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3069  -14.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3107  -15.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0299  -16.1673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7502  -15.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7464  -14.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0225  -14.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0177  -13.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4595  -14.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1753  -14.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1728  -15.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8879  -16.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6018  -15.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5963  -14.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8807  -14.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1649  -14.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0749  -13.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2677  -13.5275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8556  -14.2425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4082  -14.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4566  -13.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3066  -14.4844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3008  -13.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1697  -13.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1668  -12.4369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8799  -12.0220    0.0000 C   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
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  1 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 19  1  0
 12 24  1  0
 25 26  1  0
 17 25  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4753687

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 389.46

Molecular Weight (Monoisotopic): 389.1852

AlogP: 2.99

#Rotatable Bonds: 7

Polar Surface Area: 84.83

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.95

CX LogP: 2.22

CX LogD: -0.25

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: -1.00

References

1. Xu G,Gaul MD,Liu Z,DesJarlais RL,Qi J,Wang W,Krosky D,Petrounia I,Milligan CM,Hermans A,Lu HR,Huang DZ,Xu JZ,Spurlino JC.  (2020)  Hit-to-lead optimization and discovery of a potent, and orally bioavailable G protein coupled receptor kinase 2 (GRK2) inhibitor.,  30  (23): [PMID:33038544] [10.1016/j.bmcl.2020.127602]

Source

Source(1):

• Scientific Literature