US8969335, A37

ID: ALA3687178

PubChem CID: 71295151

Max Phase: Preclinical

Molecular Formula: C23H21N5O3

Molecular Weight: 415.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cc(-c2ccnc(Nc3ccc(C(N)=O)cn3)c2)ccc1OC1CCOCC1

Standard InChI:  InChI=1S/C23H21N5O3/c24-13-18-11-15(1-3-20(18)31-19-6-9-30-10-7-19)16-5-8-26-22(12-16)28-21-4-2-17(14-27-21)23(25)29/h1-5,8,11-12,14,19H,6-7,9-10H2,(H2,25,29)(H,26,27,28)

Standard InChI Key:  QCTBKGPTHUVEKR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    3.6375   -0.9049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -2.7031    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
    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
   -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
   -5.2007    1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4972    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4920   -0.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1903   -1.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8939   -0.7546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7994    1.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8071    2.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1099    3.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4052    2.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7072    3.7157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7126    5.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0128    5.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0152    7.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7174    8.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4171    7.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4147    5.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3976    1.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0948    0.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6935    0.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7297    0.1070    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
  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  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  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 20  1  0
 18 26  1  0
 26 27  2  0
 27 15  1  0
 26 28  1  0
 28 29  3  0
  7 30  1  0
 30 31  2  0
 31  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3687178

   6-[[4-[3-Cyano-4-(oxan-4-yloxy)phenyl]pyridin-2-yl]amino]pyridine-3-carboxamide

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: 415.45

Molecular Weight (Monoisotopic): 415.1644

AlogP: 3.42

#Rotatable Bonds: 6

Polar Surface Area: 123.15

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.75

CX Basic pKa: 4.36

CX LogP: 2.32

CX LogD: 2.32

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.63

Np Likeness Score: -0.86

References

1.  (2015)  Benzonitrile derivatives as kinase inhibitors, 

Source

Source(1):

• BindingDB Database