3-(4-Chlorobenzyl)-2-methyl-5-(4-(trifluoromethyl)phenyl)pyrazolo[1,5a]pyrimidin-7(4H)-one

ID: ALA3717637

PubChem CID: 70925394

Max Phase: Preclinical

Molecular Formula: C21H15ClF3N3O

Molecular Weight: 417.82

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H15ClF3N3O/c1-12-17(10-13-2-8-16(22)9-3-13)20-26-18(11-19(29)28(20)27-12)14-4-6-15(7-5-14)21(23,24)25/h2-9,11,26H,10H2,1H3

Standard InChI Key:  BQHRCRKIQNFUHX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -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
   -7.5198   -3.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5233   -4.9368    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5575   -3.1341    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5607   -4.3339    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
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  2  3  2  0
  3  4  1  0
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  5  6  1  0
  6  7  2  0
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  3 11  1  0
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 15 13  2  0
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  8 17  1  0
  7 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
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 26 29  1  0
 16 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3717637

   3-[(4-chlorophenyl)methyl]-2-methyl-5-[4-(trifluoromethyl)phenyl]-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: 417.82

Molecular Weight (Monoisotopic): 417.0856

AlogP: 5.26

#Rotatable Bonds: 3

Polar Surface Area: 50.16

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.31

CX Basic pKa: 0.41

CX LogP: 5.11

CX LogD: 5.11

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -1.33

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