US9303033, U36, Table 41A, Compound 7

ID: ALA3987091

PubChem CID: 137316448

Max Phase: Preclinical

Molecular Formula: C21H27N9O3

Molecular Weight: 453.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)N[C@H]1CC[C@H](Nc2nc(NC3CC3)n3ncc(/C=C4\NC(=O)NC4=O)c3n2)CC1

Standard InChI:  InChI=1S/C21H27N9O3/c1-2-16(31)23-12-3-5-13(6-4-12)24-19-27-17-11(9-15-18(32)28-21(33)26-15)10-22-30(17)20(29-19)25-14-7-8-14/h9-10,12-14H,2-8H2,1H3,(H,23,31)(H2,24,25,27,29)(H2,26,28,32,33)/b15-9-/t12-,13-

Standard InChI Key:  IDQPGNAUNOEMOA-JNZTXQQWSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  1  0  0  0  0  0999 V2000
    4.9168  -10.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8788   -9.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8809   -8.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9211   -7.6596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5826   -7.5048    0.0000 N   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
    1.2935   -3.7495    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
    3.8915   -3.7585    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
    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
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  6  5  1  6
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  6  1  0
  9 12  1  1
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 17  1  0
 15 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 25  1  0
 30 31  2  0
 23 32  2  0
 32 20  1  0
 32 33  1  0
 33 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3987091

   ---

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: 453.51

Molecular Weight (Monoisotopic): 453.2237

AlogP: 1.13

#Rotatable Bonds: 7

Polar Surface Area: 154.44

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.24

CX Basic pKa: 2.27

CX LogP: 0.27

CX LogD: -0.11

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.31

Np Likeness Score: -1.04

References

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

Source

Source(1):

• BindingDB Database