4-(3-(4-Chlorobenzyl)-2-methyl-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidin-5yl)benzamide

ID: ALA3718878

PubChem CID: 70925371

Max Phase: Preclinical

Molecular Formula: C21H17ClN4O2

Molecular Weight: 392.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nn2c(=O)cc(-c3ccc(C(N)=O)cc3)[nH]c2c1Cc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C21H17ClN4O2/c1-12-17(10-13-2-8-16(22)9-3-13)21-24-18(11-19(27)26(21)25-12)14-4-6-15(7-5-14)20(23)28/h2-9,11,24H,10H2,1H3,(H2,23,28)

Standard InChI Key:  OHNSQRVMAFFGPN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  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
    7.7700   -3.7717    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.5214   -3.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5584   -3.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5262   -4.9341    0.0000 N   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
 22 25  1  0
 16 26  1  0
 26 27  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3718878

   4-[3-[(4-chlorophenyl)methyl]-2-methyl-7-oxo-1H-pyrazolo[1,5-a]pyrimidin-5-yl]benzamide

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: 392.85

Molecular Weight (Monoisotopic): 392.1040

AlogP: 3.34

#Rotatable Bonds: 4

Polar Surface Area: 93.25

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.28

CX Basic pKa: 0.18

CX LogP: 3.08

CX LogD: 3.08

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: -1.25

References

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

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

Source

Source(1):

• Patent Bioactivity Data