US8969335, A44

ID: ALA3687185

PubChem CID: 71295228

Max Phase: Preclinical

Molecular Formula: C21H20F2N6O2

Molecular Weight: 426.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cc(-c2ccnc(Nc3cnn(CC(F)F)c3)n2)ccc1OC1CCOCC1

Standard InChI:  InChI=1S/C21H20F2N6O2/c22-20(23)13-29-12-16(11-26-29)27-21-25-6-3-18(28-21)14-1-2-19(15(9-14)10-24)31-17-4-7-30-8-5-17/h1-3,6,9,11-12,17,20H,4-5,7-8,13H2,(H,25,27,28)

Standard InChI Key:  XBFXJAXJSWLRPR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.2938   -8.8527    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5939   -7.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3998   -7.9971    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2111   -6.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372   -5.2929    0.0000 N   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
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    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 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
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  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
 13 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  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3687185

   5-[2-[[1-(2,2-Difluoroethyl)pyrazol-4-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: 426.43

Molecular Weight (Monoisotopic): 426.1616

AlogP: 3.78

#Rotatable Bonds: 7

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: 10.66

CX Basic pKa: 1.89

CX LogP: 2.76

CX LogD: 2.76

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.61

Np Likeness Score: -1.63

References

1.  (2015)  Benzonitrile derivatives as kinase inhibitors, 

Source

Source(1):

• BindingDB Database