US8969335, A42

ID: ALA3687183

PubChem CID: 71509430

Max Phase: Preclinical

Molecular Formula: C25H21N5O4

Molecular Weight: 455.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cc(-c2ccnc(Nc3ccc4oc(C(N)=O)cc4c3)n2)ccc1OC1CCOCC1

Standard InChI:  InChI=1S/C25H21N5O4/c26-14-17-11-15(1-3-22(17)33-19-6-9-32-10-7-19)20-5-8-28-25(30-20)29-18-2-4-21-16(12-18)13-23(34-21)24(27)31/h1-5,8,11-13,19H,6-7,9-10H2,(H2,27,31)(H,28,29,30)

Standard InChI Key:  FONLVAFSTIESFR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    3.7497   -4.4245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497   -4.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9482   -5.4607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 O   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
   -2.6003    1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2007    1.4909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4972    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4920   -0.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1903   -1.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8939   -0.7546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4804   -3.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4728   -5.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1700   -6.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1655   -7.5107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4625   -8.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4602   -9.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7581  -10.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0583   -9.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0607   -8.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7629   -7.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8748   -5.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823   -3.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5712   -5.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5290   -6.5919    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
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
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 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 22  1  0
 20 28  1  0
 28 29  2  0
 29 17  1  0
 28 30  1  0
 30 31  3  0
  9 32  1  0
 32 33  2  0
 33  6  1  0
 33 34  1  0
 34  4  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3687183

   5-[[4-[3-Cyano-4-(oxan-4-yloxy)phenyl]pyrimidin-2-yl]amino]-1-benzofuran-2-carboxamide

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: 455.47

Molecular Weight (Monoisotopic): 455.1594

AlogP: 4.16

#Rotatable Bonds: 6

Polar Surface Area: 136.29

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.90

CX Basic pKa: 2.01

CX LogP: 2.79

CX LogD: 2.79

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.44

Np Likeness Score: -1.01

References

1.  (2015)  Benzonitrile derivatives as kinase inhibitors, 

Source

Source(1):

• BindingDB Database