US8969335, A35

ID: ALA3687176

PubChem CID: 71295246

Max Phase: Preclinical

Molecular Formula: C22H24N6O3

Molecular Weight: 420.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCn1cc(Nc2nccc(-c3ccc(OC4CCOCC4)c(C#N)c3)n2)cn1

Standard InChI:  InChI=1S/C22H24N6O3/c1-29-11-8-28-15-18(14-25-28)26-22-24-7-4-20(27-22)16-2-3-21(17(12-16)13-23)31-19-5-9-30-10-6-19/h2-4,7,12,14-15,19H,5-6,8-11H2,1H3,(H,24,26,27)

Standard InChI Key:  TUHJNJJPZVPTPS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.9758  -10.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4693   -9.0970    0.0000 O   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
    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
  3  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:

   

   ALA3687176

   5-{2-[1-(2-Methoxyethyl)-1H-pyrazol-4-ylamino]pyrimidin-4-yl}-2-(tetrahydropyran-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: 420.47

Molecular Weight (Monoisotopic): 420.1910

AlogP: 3.16

#Rotatable Bonds: 8

Polar Surface Area: 107.11

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.67

CX Basic pKa: 1.93

CX LogP: 2.24

CX LogD: 2.24

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.59

Np Likeness Score: -1.63

References

1.  (2015)  Benzonitrile derivatives as kinase inhibitors, 

Source

Source(1):

• BindingDB Database