US8969335, A27

ID: ALA3687169

PubChem CID: 71295166

Max Phase: Preclinical

Molecular Formula: C25H27N5O3

Molecular Weight: 445.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cc(-c2ccnc(Nc3cnn(CC4CCOC4)c3)c2)ccc1OC1CCOCC1

Standard InChI:  InChI=1S/C25H27N5O3/c26-13-21-11-19(1-2-24(21)33-23-5-9-31-10-6-23)20-3-7-27-25(12-20)29-22-14-28-30(16-22)15-18-4-8-32-17-18/h1-3,7,11-12,14,16,18,23H,4-6,8-10,15,17H2,(H,27,29)

Standard InChI Key:  XXSJUYSLBGBRGF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    3.6380   -2.1004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -1.5004    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 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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -3.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092   -5.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108   -5.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9072   -5.2404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9020   -3.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004   -2.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978    3.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2954    5.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0048    6.0009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3026    5.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051    5.9945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9026    5.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2571    5.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2552    4.7345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4986    3.4393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0982    2.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2081    0.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6724   -0.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4514   -1.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2454   -0.5343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212    0.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0330    3.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3002    3.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 10  1  0
  5 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 27  1  0
 25 32  1  0
 32 22  2  0
 20 33  2  0
 33 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3687169

   2-(Oxan-4-yloxy)-5-[2-[[1-(oxolan-3-ylmethyl)pyrazol-4-yl]amino]pyridin-4-yl]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: 445.52

Molecular Weight (Monoisotopic): 445.2114

AlogP: 4.15

#Rotatable Bonds: 7

Polar Surface Area: 94.22

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.04

CX LogP: 2.54

CX LogD: 2.54

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.58

Np Likeness Score: -0.99

References

1.  (2015)  Benzonitrile derivatives as kinase inhibitors, 

Source

Source(1):

• BindingDB Database