Methyl4-(3-(4-chlorobenzyl)-2-methyl-7-oxo-4,7-dihydropyrazolo[1,5a]pyrimidin-5-yl)benzoate

ID: ALA3718477

PubChem CID: 70925367

Max Phase: Preclinical

Molecular Formula: C22H18ClN3O3

Molecular Weight: 407.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(-c2cc(=O)n3nc(C)c(Cc4ccc(Cl)cc4)c3[nH]2)cc1

Standard InChI:  InChI=1S/C22H18ClN3O3/c1-13-18(11-14-3-9-17(23)10-4-14)21-24-19(12-20(27)26(21)25-13)15-5-7-16(8-6-15)22(28)29-2/h3-10,12,24H,11H2,1-2H3

Standard InChI Key:  LUAGMQSANAOCGC-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
   -7.5214   -3.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5262   -4.9341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8184   -2.9789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8602   -3.5744    0.0000 C   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
  4  6  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
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  1 10  2  0
  3 11  1  0
 11 12  2  0
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 15 13  2  0
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 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
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3718477

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

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: 407.86

Molecular Weight (Monoisotopic): 407.1037

AlogP: 4.03

#Rotatable Bonds: 4

Polar Surface Area: 76.46

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.27

CX Basic pKa: 0.03

CX LogP: 4.23

CX LogD: 4.23

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.52

Np Likeness Score: -1.05

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