US9303033, E46, Table 51A, Compound 4

ID: ALA3986376

PubChem CID: 136483859

Max Phase: Preclinical

Molecular Formula: C23H21N9O2

Molecular Weight: 455.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Nc2ccc(-n3cccn3)cc2)nc2c(/C=C3\NC(=O)NC3=O)cnn2c1NC1CC1

Standard InChI:  InChI=1S/C23H21N9O2/c1-13-19(26-15-5-7-17(8-6-15)31-10-2-9-24-31)29-21-14(11-18-22(33)30-23(34)28-18)12-25-32(21)20(13)27-16-3-4-16/h2,5-12,16,27H,3-4H2,1H3,(H,26,29)(H2,28,30,33,34)/b18-11-

Standard InChI Key:  YCIVLENCEVEADC-WQRHYEAKSA-N

Molfile:  

     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.5031    0.0000 N   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
    3.8915    3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8863    5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847    6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2883    5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2934    3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5795    7.5047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7887    8.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3179    9.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179    9.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616    8.3585    0.0000 N   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
   -1.2990    0.7500    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
   -3.1905    2.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6589    2.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7489    1.9359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0504    2.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1450    2.1899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7434    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
   -4.6494    5.3492    0.0000 O   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 N   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   -3.6986    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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
  3 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 20  1  0
 25 26  2  0
 18 27  1  0
 27 28  2  0
 28 29  1  0
 29 17  1  0
 29 30  1  0
 30  2  2  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986376

   ---

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: 455.48

Molecular Weight (Monoisotopic): 455.1818

AlogP: 2.72

#Rotatable Bonds: 6

Polar Surface Area: 130.27

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: 2.94

CX LogP: 2.02

CX LogD: 1.64

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.26

Np Likeness Score: -1.68

References

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

Source

Source(1):

• BindingDB Database