US9303033, X20, Table 37A, Compound 24

ID: ALA3985479

PubChem CID: 137316510

Max Phase: Preclinical

Molecular Formula: C21H27N9O3

Molecular Weight: 453.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)/C(=C/c2cnn3c(NC4CC4)nc(NCC4(CN5CCOCC5)CC4)nc23)N1

Standard InChI:  InChI=1S/C21H27N9O3/c31-17-15(25-20(32)27-17)9-13-10-23-30-16(13)26-18(28-19(30)24-14-1-2-14)22-11-21(3-4-21)12-29-5-7-33-8-6-29/h9-10,14H,1-8,11-12H2,(H2,22,24,26,28)(H2,25,27,31,32)/b15-9-

Standard InChI Key:  LDSYBLNRDRBJID-DHDCSXOGSA-N

Molfile:  

     RDKit          2D

 33 38  0  0  0  0  0  0  0  0999 V2000
    2.1760   -8.1488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2028   -7.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222   -7.9149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1079   -6.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3079   -6.7011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2234   -5.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6890   -4.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    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
    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
    3.3408    4.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408    4.2089    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
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4991    0.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8006    1.4876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0995    0.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3988    1.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3993    2.9868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1005    3.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8012    2.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9525    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4525    2.6605    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
    1.1979   -5.9466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 14  1  0
 12 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 23  1  0
 21 29  1  0
 29 30  1  0
 30 21  1  0
 18 31  2  0
 31 32  1  0
 32  8  2  0
 32 11  1  0
  6 33  1  0
 33  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3985479

   ---

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: 0.40

#Rotatable Bonds: 8

Polar Surface Area: 137.81

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.24

CX Basic pKa: 6.72

CX LogP: -0.62

CX LogD: -0.68

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: -1.03

References

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

Source

Source(1):

• BindingDB Database