5-(3-Ethylbenzo[d]isoxazol-6-yl)-3-(oxazol-2-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one

ID: ALA3715861

PubChem CID: 90109370

Max Phase: Preclinical

Molecular Formula: C18H13N5O3

Molecular Weight: 347.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1noc2cc(-c3cc(=O)n4ncc(-c5ncco5)c4[nH]3)ccc12

Standard InChI:  InChI=1S/C18H13N5O3/c1-2-13-11-4-3-10(7-15(11)26-22-13)14-8-16(24)23-17(21-14)12(9-20-23)18-19-5-6-25-18/h3-9,21H,2H2,1H3

Standard InChI Key:  XPLGHUMUWMJNMF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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
    1.3751    3.8801    0.0000 O   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
    3.6243    2.9682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7308    4.4644    0.0000 C   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
   -7.6468    1.0526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5184    2.2403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6395    3.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2188    2.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2234    1.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9312    0.7344    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
   -3.6117    2.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9221    3.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1069    4.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2813    5.1293    0.0000 C   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
  9 12  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 16 20  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 20 21  2  0
 25 26  1  0
 18 25  1  0
  3 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3715861

   5-(3-ethylbenzo[d]isoxazol-6-yl)-3-(oxazol-2-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-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: 347.33

Molecular Weight (Monoisotopic): 347.1018

AlogP: 3.05

#Rotatable Bonds: 3

Polar Surface Area: 102.22

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.64

CX Basic pKa: 0.33

CX LogP: 1.59

CX LogD: 1.59

Aromatic Rings: 5

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: -1.28

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