US9303033, R23, Table 37A, Compound 95

ID: ALA3987142

PubChem CID: 136506964

Max Phase: Preclinical

Molecular Formula: C21H22N8O2

Molecular Weight: 418.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(Nc1nc(NC2CC2)n2ncc(/C=C3\NC(=O)NC3=O)c2n1)c1ccccc1

Standard InChI:  InChI=1S/C21H22N8O2/c1-21(2,13-6-4-3-5-7-13)28-18-25-16-12(10-15-17(30)26-20(31)24-15)11-22-29(16)19(27-18)23-14-8-9-14/h3-7,10-11,14H,8-9H2,1-2H3,(H2,23,25,27,28)(H2,24,26,30,31)/b15-10-

Standard InChI Key:  QQKVOBGEFLRZRS-GDNBJRDFSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
    1.5548   -3.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5568   -2.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792    5.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7246    3.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248    1.2135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6065    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248   -1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904   -2.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6588   -2.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7489   -1.9360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0504   -2.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1450   -2.1900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7433   -4.1499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2521   -4.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6493   -5.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8902   -5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1877   -6.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4883   -5.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4914   -3.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1939   -3.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  9  1  0
  7 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 17  1  0
 22 23  2  0
 15 24  2  0
 24 12  1  0
 24 25  1  0
 25  5  2  0
  2 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3987142

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 418.46

Molecular Weight (Monoisotopic): 418.1866

AlogP: 2.23

#Rotatable Bonds: 6

Polar Surface Area: 125.34

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.24

CX Basic pKa: 2.25

CX LogP: 1.87

CX LogD: 1.49

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.36

Np Likeness Score: -1.04

References

1.  (2016)  Pyrazolopyrimidines and related heterocycles as CK2 inhibitors, 

Source

Source(1):

• BindingDB Database