US9303033, V30, Table 37A, Compound 281

ID: ALA3985559

PubChem CID: 136483991

Max Phase: Preclinical

Molecular Formula: C20H19ClN8O3

Molecular Weight: 454.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)/C(=C/c2cnn3c(NC4CC4)nc(NCCOc4cccc(Cl)c4)nc23)N1

Standard InChI:  InChI=1S/C20H19ClN8O3/c21-12-2-1-3-14(9-12)32-7-6-22-18-26-16-11(8-15-17(30)27-20(31)25-15)10-23-29(16)19(28-18)24-13-4-5-13/h1-3,8-10,13H,4-7H2,(H2,22,24,26,28)(H2,25,27,30,31)/b15-8-

Standard InChI Key:  BQCBGRPRQUYQMC-NVNXTCNLSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    8.8268   -5.4110    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.7876   -6.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7875   -7.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4885   -8.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1895   -7.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 O   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
    6.4885   -5.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 15  1  0
 13 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 23  1  0
 28 29  2  0
 21 30  2  0
 30 18  1  0
 30 31  1  0
 31 11  2  0
  6 32  2  0
 32  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3985559

   ---

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: 454.88

Molecular Weight (Monoisotopic): 454.1269

AlogP: 2.02

#Rotatable Bonds: 8

Polar Surface Area: 134.57

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: 2.34

CX LogP: 1.69

CX LogD: 1.31

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.23

Np Likeness Score: -1.45

References

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

Source

Source(1):

• BindingDB Database