6-(3-cyano-4-isopentyloxyphenyl)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one

ID: ALA5202331

PubChem CID: 156705026

Max Phase: Preclinical

Molecular Formula: C17H17N5O2

Molecular Weight: 323.36

Names and Identifiers

Canonical SMILES:  CC(C)CCOc1ccc(-c2ncc3c(=O)[nH][nH]c3n2)cc1C#N

Standard InChI:  InChI=1S/C17H17N5O2/c1-10(2)5-6-24-14-4-3-11(7-12(14)8-18)15-19-9-13-16(20-15)21-22-17(13)23/h3-4,7,9-10H,5-6H2,1-2H3,(H2,19,20,21,22,23)

Standard InChI Key:  QULVRWGNRWFLOG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -1.3446    0.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301    1.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0817    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0817   -0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6282   -0.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446   -0.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0593   -0.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0593   -1.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7739   -1.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7739   -2.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4886   -3.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0593   -3.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6282   -1.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6282   -2.1728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7964    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7966    1.9523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5095    2.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2244    1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2259    1.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5141    0.7127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0072    0.8769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0047    2.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4886    1.5421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2183    3.0025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  5 13  1  0
 13 14  3  0
 15  3  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 15 20  1  0
 19 21  1  0
 18 22  1  0
 22 23  1  0
 23 21  1  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5202331

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 323.36

Molecular Weight (Monoisotopic): 323.1382

AlogP: 2.61

#Rotatable Bonds: 5

Polar Surface Area: 107.45

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.51

CX Basic pKa: 3.71

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.75

Np Likeness Score: -1.12

References

1. Zhao J, Mao Q, Lin F, Zhang B, Sun M, Zhang T, Wang S..  (2022)  Intramolecular hydrogen bond interruption and scaffold hopping of TMC-5 led to 2-(4-alkoxy-3-cyanophenyl)pyrimidine-4/5-carboxylic acids and 6-(4-alkoxy-3-cyanophenyl)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-ones as potent pyrimidine-based xanthine oxidase inhibitors.,  229  [PMID:34992040] [10.1016/j.ejmech.2021.114086]

Source

Source(1):

• Scientific Literature