US9303033, E26, Table 37A, Compound 160

ID: ALA3985801

PubChem CID: 136128086

Max Phase: Preclinical

Molecular Formula: C19H20N8O3

Molecular Weight: 408.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(CNc2nc(NC3CC3)n3ncc(/C=C4\NC(=O)NC4=O)c3n2)c(C)o1

Standard InChI:  InChI=1S/C19H20N8O3/c1-9-5-11(10(2)30-9)7-20-17-24-15-12(6-14-16(28)25-19(29)23-14)8-21-27(15)18(26-17)22-13-3-4-13/h5-6,8,13H,3-4,7H2,1-2H3,(H2,20,22,24,26)(H2,23,25,28,29)/b14-6-

Standard InChI Key:  PKSISZCZHWUASX-NSIKDUERSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    7.4419   -4.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2484   -4.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4984   -5.5497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312   -5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1347   -6.0355    0.0000 C   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
    2.5951   -3.0039    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
    5.2447   -3.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 13  1  0
 11 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 21  1  0
 26 27  2  0
 19 28  2  0
 28 16  1  0
 28 29  1  0
 29  9  2  0
  6 30  1  0
 30  2  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3985801

   ---

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: 408.42

Molecular Weight (Monoisotopic): 408.1658

AlogP: 1.70

#Rotatable Bonds: 6

Polar Surface Area: 138.48

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.24

CX Basic pKa: 2.31

CX LogP: 0.71

CX LogD: 0.33

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: -1.13

References

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

Source

Source(1):

• BindingDB Database