3-(4-Chlorobenzyl)-5-(3,4-dimethoxyphenyl)-2-methylpyrazolo[1,5a]pyrimidin-7(4H)-one

ID: ALA3718262

PubChem CID: 70925532

Max Phase: Preclinical

Molecular Formula: C22H20ClN3O3

Molecular Weight: 409.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cc(=O)n3nc(C)c(Cc4ccc(Cl)cc4)c3[nH]2)cc1OC

Standard InChI:  InChI=1S/C22H20ClN3O3/c1-13-17(10-14-4-7-16(23)8-5-14)22-24-18(12-21(27)26(22)25-13)15-6-9-19(28-2)20(11-15)29-3/h4-9,11-12,24H,10H2,1-3H3

Standard InChI Key:  NSEBYRNEYMXQMS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991    2.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6168   -1.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6203   -2.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9143   -0.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9210   -3.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2150   -1.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2184   -2.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -2.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1295   -4.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5991   -4.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5944   -3.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1201   -2.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6506   -1.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5115   -0.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5071    0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5183   -3.7395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5193   -4.9395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7700   -3.7717    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  6  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  1 10  2  0
  3 11  1  0
 11 12  2  0
 12 14  1  0
 15 13  2  0
 13 11  1  0
 16 14  2  0
 15 16  1  0
  8 17  1  0
  7 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 15 25  1  0
 25 26  1  0
 16 27  1  0
 27 28  1  0
 22 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3718262

   3-[(4-chlorophenyl)methyl]-5-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrazolo[1,5-a]pyrimidin-7-one

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: 409.87

Molecular Weight (Monoisotopic): 409.1193

AlogP: 4.26

#Rotatable Bonds: 5

Polar Surface Area: 68.62

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.32

CX Basic pKa: 0.31

CX LogP: 3.92

CX LogD: 3.92

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -0.93

References

1.  (2012)  Heterocyclic compounds for the inhibition of pask, 

2.  (2012)  Heterocyclic compounds for the inhibition of pask, 

3. Klaeger, Susan S and 47 more authors.  2017-12-01  The target landscape of clinical kinase drugs.  [PMID:29191878]

Source

Source(1):

• Patent Bioactivity Data