6-[(2-hydroxyanilino)methyl]-1-phenyl-5H-pyrazolo[3,4-d]pyrimidin-4-one

ID: ALA4785159

PubChem CID: 162666278

Max Phase: Preclinical

Molecular Formula: C18H15N5O2

Molecular Weight: 333.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(CNc2ccccc2O)nc2c1cnn2-c1ccccc1

Standard InChI:  InChI=1S/C18H15N5O2/c24-15-9-5-4-8-14(15)19-11-16-21-17-13(18(25)22-16)10-20-23(17)12-6-2-1-3-7-12/h1-10,19,24H,11H2,(H,21,22,25)

Standard InChI Key:  BAELQTMCMHUMBQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    5.3856  -14.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6773  -14.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6773  -15.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3882  -16.1281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0942  -15.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0942  -14.8986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8106  -16.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5228  -15.7190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2349  -16.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9515  -15.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6642  -16.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6642  -16.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9540  -17.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2349  -16.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9515  -14.8945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8934  -15.9775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4062  -15.3116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8935  -14.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6789  -16.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8811  -16.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6691  -17.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2532  -18.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0465  -18.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2611  -17.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3856  -13.6645    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
  3 16  1  0
 16 17  1  0
 17 18  2  0
  2 18  1  0
 19 16  1  0
 19 20  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 24 23  1  0
 24 19  2  0
  1 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4785159

   ---

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: 333.35

Molecular Weight (Monoisotopic): 333.1226

AlogP: 2.43

#Rotatable Bonds: 4

Polar Surface Area: 95.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.93

CX Basic pKa: 3.72

CX LogP: 1.79

CX LogD: 1.78

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.50

Np Likeness Score: -1.78

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