US8969335, A33

ID: ALA3687174

PubChem CID: 71295165

Max Phase: Preclinical

Molecular Formula: C20H20N6O2

Molecular Weight: 376.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1ccc(Nc2nccc(-c3ccc(OC4CCOCC4)c(C#N)c3)n2)n1

Standard InChI:  InChI=1S/C20H20N6O2/c1-26-9-5-19(25-26)24-20-22-8-4-17(23-20)14-2-3-18(15(12-14)13-21)28-16-6-10-27-11-7-16/h2-5,8-9,12,16H,6-7,10-11H2,1H3,(H,22,23,24,25)

Standard InChI Key:  GVEFUAPLXFCYLH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    1.1285   -6.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -5.2877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372   -5.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056   -3.8679    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 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
   -1.2990    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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969   -1.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1945   -3.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4946   -3.7544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7945   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0950   -3.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3926   -2.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3898   -1.4993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0894   -0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7918   -1.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8919   -5.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8900   -6.4533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786   -3.8595    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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  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 18  1  0
 16 24  1  0
 24 25  2  0
 25 13  1  0
 24 26  1  0
 26 27  3  0
  5 28  2  0
 28  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3687174

   5-[2-[(1-Methylpyrazol-3-yl)amino]pyrimidin-4-yl]-2-(oxan-4-yloxy)benzonitrile

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: 376.42

Molecular Weight (Monoisotopic): 376.1648

AlogP: 3.05

#Rotatable Bonds: 5

Polar Surface Area: 97.88

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.02

CX Basic pKa: 1.28

CX LogP: 2.88

CX LogD: 2.87

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.73

Np Likeness Score: -1.40

References

1.  (2015)  Benzonitrile derivatives as kinase inhibitors, 

Source

Source(1):

• BindingDB Database