methyl 2-[(4-oxo-1-phenyl-5H-pyrazolo[3,4-d]pyrimidin-6-yl)methoxy]benzoate

ID: ALA4790850

PubChem CID: 162671385

Max Phase: Preclinical

Molecular Formula: C20H16N4O4

Molecular Weight: 376.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccccc1OCc1nc2c(cnn2-c2ccccc2)c(=O)[nH]1

Standard InChI:  InChI=1S/C20H16N4O4/c1-27-20(26)14-9-5-6-10-16(14)28-12-17-22-18-15(19(25)23-17)11-21-24(18)13-7-3-2-4-8-13/h2-11H,12H2,1H3,(H,22,23,25)

Standard InChI Key:  OFDUSMVPGGANBN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   11.7899   -6.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0780   -6.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0780   -7.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7935   -8.1181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4980   -7.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4980   -6.8866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2171   -8.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9303   -7.7086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6476   -8.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3629   -7.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0769   -8.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0769   -8.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3666   -9.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6477   -8.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3629   -6.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6463   -6.4705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0796   -6.4705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0796   -5.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2958   -7.9695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8099   -7.3016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2959   -6.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0768   -8.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2788   -8.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0677   -9.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6521  -10.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4537  -10.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6628   -9.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7899   -5.6487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  1  6  1  0
  7  5  1  0
  7  8  1  0
  8  9  1  0
 10  9  2  0
 11 10  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
  9 14  1  0
 10 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
  3 19  1  0
 19 20  1  0
 20 21  2  0
  2 21  1  0
 22 19  1  0
 22 23  1  0
 24 23  2  0
 25 24  1  0
 26 25  2  0
 27 26  1  0
 27 22  2  0
  1 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4790850

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 376.37

Molecular Weight (Monoisotopic): 376.1172

AlogP: 2.47

#Rotatable Bonds: 5

Polar Surface Area: 99.10

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.73

CX Basic pKa: ┄

CX LogP: 2.47

CX LogD: 2.45

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -1.67

References

1. Shaaban MA,Elshaier YAMM,Hammad AH,Farag NA,Hassan Haredy H,AbdEl-Ghany AA,Mohamed KO.  (2020)  Design and synthesis of pyrazolo[3,4-d]pyrimidinone derivatives: Discovery of selective phosphodiesterase-5 inhibitors.,  30  (16): [PMID:32631538] [10.1016/j.bmcl.2020.127337]

Source

Source(1):

• Scientific Literature