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

ID: ALA5205761

PubChem CID: 156705019

Max Phase: Preclinical

Molecular Formula: C19H19N5O2

Molecular Weight: 349.39

Names and Identifiers

Canonical SMILES:  N#Cc1cc(-c2ncc3c(=O)[nH][nH]c3n2)ccc1OCC1CCCCC1

Standard InChI:  InChI=1S/C19H19N5O2/c20-9-14-8-13(17-21-10-15-18(22-17)23-24-19(15)25)6-7-16(14)26-11-12-4-2-1-3-5-12/h6-8,10,12H,1-5,11H2,(H2,21,22,23,24,25)

Standard InChI Key:  RGDYQVIELSOMJA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -0.2727    1.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4390    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4390   -0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2710   -0.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9873   -0.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7020   -0.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7020   -1.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166   -1.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166   -2.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1312   -3.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8459   -2.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8459   -1.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1312   -1.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2710   -1.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2710   -2.1728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1537    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1539    1.9523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667    2.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5816    1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5832    1.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8714    0.7127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3645    0.8769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3620    2.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8459    1.5421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5756    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
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 11 12  1  0
 13 12  1  0
 14 13  1  0
  9 14  1  0
  5 15  1  0
 15 16  3  0
 17  3  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
 21 23  1  0
 20 24  1  0
 24 25  1  0
 25 23  1  0
 24 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5205761

   ---

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: 349.39

Molecular Weight (Monoisotopic): 349.1539

AlogP: 3.14

#Rotatable Bonds: 4

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: 4.16

CX LogD: 4.16

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.75

Np Likeness Score: -1.15

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