US9303033, O40, Table 43A, Compound 44

ID: ALA3986917

PubChem CID: 137316455

Max Phase: Preclinical

Molecular Formula: C20H18N8O3

Molecular Weight: 418.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1ccc(Nc2cc(NC3CC3)n3ncc(/C=C4\NC(=O)NC4=O)c3n2)cc1

Standard InChI:  InChI=1S/C20H18N8O3/c21-17(29)10-1-3-12(4-2-10)23-15-8-16(24-13-5-6-13)28-18(26-15)11(9-22-28)7-14-19(30)27-20(31)25-14/h1-4,7-9,13,24H,5-6H2,(H2,21,29)(H,23,26)(H2,25,27,30,31)/b14-7-

Standard InChI Key:  UDERYNHIEXUJKS-AUWJEWJLSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
    3.6126   -8.1102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765   -7.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5343   -8.0997    0.0000 O   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
    3.8864   -5.2585    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
    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 C   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
    1.2935   -3.7495    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  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  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
  7 30  1  0
 30 31  2  0
 31  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986917

   ---

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: 418.42

Molecular Weight (Monoisotopic): 418.1502

AlogP: 1.33

#Rotatable Bonds: 6

Polar Surface Area: 155.54

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.24

CX Basic pKa: 2.64

CX LogP: 0.27

CX LogD: -0.11

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.30

Np Likeness Score: -1.20

References

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

Source

Source(1):

• BindingDB Database