4-[(3-chloro-4-methoxy-phenyl)methylamino]-2-[(3R)-3-(hydroxymethyl)-3,4-dihydro-1H-isoquinolin-2-yl]-N-(2-pyridylmethyl)pyrimidine-5-carboxamide

ID: ALA4741817

PubChem CID: 162645480

Max Phase: Preclinical

Molecular Formula: C29H29ClN6O3

Molecular Weight: 545.04

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(CNc2nc(N3Cc4ccccc4C[C@@H]3CO)ncc2C(=O)NCc2ccccn2)cc1Cl

Standard InChI:  InChI=1S/C29H29ClN6O3/c1-39-26-10-9-19(12-25(26)30)14-32-27-24(28(38)33-15-22-8-4-5-11-31-22)16-34-29(35-27)36-17-21-7-3-2-6-20(21)13-23(36)18-37/h2-12,16,23,37H,13-15,17-18H2,1H3,(H,33,38)(H,32,34,35)/t23-/m1/s1

Standard InChI Key:  WDBFSZFOLCDJAC-HSZRJFAPSA-N

Molfile:  

 
     RDKit          2D

 39 43  0  0  0  0  0  0  0  0999 V2000
   30.7836  -15.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7824  -16.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4946  -16.9821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.2084  -16.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2056  -15.7459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4928  -15.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9209  -16.9801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0703  -16.9812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0696  -17.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3575  -18.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6477  -17.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9360  -18.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9349  -19.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6514  -19.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3602  -19.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2288  -17.7965    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.2274  -19.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5154  -19.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0716  -15.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0715  -14.5156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3599  -15.7498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3595  -14.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6478  -14.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9370  -14.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2299  -14.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2297  -15.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9425  -15.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6508  -15.3323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9179  -17.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6222  -18.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6235  -16.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3365  -16.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3319  -17.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0378  -18.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7488  -17.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7494  -16.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0429  -16.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2051  -18.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2033  -19.0341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 12 16  1  0
 13 17  1  0
 17 18  1  0
  1 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
  7 29  1  0
  7 31  1  0
 29 30  1  0
 30 33  1  0
 32 31  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 32  1  0
 29 38  1  6
 38 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4741817

   ---

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: 545.04

Molecular Weight (Monoisotopic): 544.1990

AlogP: 4.00

#Rotatable Bonds: 9

Polar Surface Area: 112.50

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.83

CX Basic pKa: 5.52

CX LogP: 4.52

CX LogD: 4.52

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.29

Np Likeness Score: -1.29

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