5-(4-chloro-3-methoxyphenyl)-2-ethyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-4H,7H-pyrazolo[1,5-a]pyrimidin-7-one

ID: ALA3718189

PubChem CID: 136509759

Max Phase: Preclinical

Molecular Formula: C18H16ClN5O3

Molecular Weight: 385.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1nn2c(=O)cc(-c3ccc(Cl)c(OC)c3)[nH]c2c1-c1nc(C)no1

Standard InChI:  InChI=1S/C18H16ClN5O3/c1-4-12-16(18-20-9(2)23-27-18)17-21-13(8-15(25)24(17)22-12)10-5-6-11(19)14(7-10)26-3/h5-8,21H,4H2,1-3H3

Standard InChI Key:  JDGOTTWGDXSELY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    0.2917    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
   -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 C   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
    1.7138   -1.2033    0.0000 N   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 C   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
    3.6243    2.9682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7308    4.4645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406    5.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3751    3.8801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    2.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0517    6.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6976   -1.0012    0.0000 C   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
   -4.9144    0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2151    1.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2185    2.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9211    3.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6204    2.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5116    0.7332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5072   -0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2590    3.5868    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  7  8  2  0
  8  9  1  0
  6  7  1  0
  1  9  2  0
  5 10  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 11 15  1  0
 13 16  1  0
  9 15  1  0
 17 18  1  0
  8 17  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 25 26  1  0
 21 25  1  0
 22 27  1  0
  3 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3718189

   ---

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: 385.81

Molecular Weight (Monoisotopic): 385.0942

AlogP: 3.27

#Rotatable Bonds: 4

Polar Surface Area: 98.31

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.59

CX Basic pKa: ┄

CX LogP: 2.98

CX LogD: 2.98

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: -1.67

References

1.  (2014)  Heterocyclic compounds for the inhibition of pask, 

2.  (2015)  Heterocyclic compounds for the inhibition of pask, 

Source

Source(1):

• Patent Bioactivity Data