US8969335, A31

ID: ALA3687173

PubChem CID: 71295250

Max Phase: Preclinical

Molecular Formula: C24H26N4O3

Molecular Weight: 418.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(Nc2cc(-c3ccc(OC4CCOCC4)c(C#N)c3)ccn2)on1

Standard InChI:  InChI=1S/C24H26N4O3/c1-24(2,3)21-14-23(31-28-21)27-22-13-17(6-9-26-22)16-4-5-20(18(12-16)15-25)30-19-7-10-29-11-8-19/h4-6,9,12-14,19H,7-8,10-11H2,1-3H3,(H,26,27)

Standard InChI Key:  IVAFRTWUCSWUMI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    5.4075   -6.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2136   -6.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7213   -7.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151   -7.4817    0.0000 C   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 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 N   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0041    7.5017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2955    8.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2984    9.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989   10.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965    9.7475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8937    8.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5933    7.4999    0.0000 C   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
   -1.3002    3.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6036    5.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6438    6.5955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786   -3.8595    0.0000 O   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
  2  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
 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  1  0
 31  5  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3687173

   5-[2-(3-tert-Butylisoxazol-5-ylamino)pyridin-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: 418.50

Molecular Weight (Monoisotopic): 418.2005

AlogP: 5.21

#Rotatable Bonds: 5

Polar Surface Area: 93.20

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.20

CX Basic pKa: 3.15

CX LogP: 4.48

CX LogD: 4.47

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.61

Np Likeness Score: -0.90

References

1.  (2015)  Benzonitrile derivatives as kinase inhibitors, 

Source

Source(1):

• BindingDB Database