US9296747, Example 16

ID: ALA3981517

PubChem CID: 118970911

Max Phase: Preclinical

Molecular Formula: C21H21N5O3

Molecular Weight: 391.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Nc2ncc3c(n2)CCN(C(=O)c2cccnc2)C3)cc1OC

Standard InChI:  InChI=1S/C21H21N5O3/c1-28-18-6-5-16(10-19(18)29-2)24-21-23-12-15-13-26(9-7-17(15)25-21)20(27)14-4-3-8-22-11-14/h3-6,8,10-12H,7,9,13H2,1-2H3,(H,23,24,25)

Standard InChI Key:  DMGSMYLIZXPVTK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    3.6206   -8.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5826   -7.5048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847   -6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864   -5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8915   -3.7585    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
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -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
    0.0000   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1984    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2005    2.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4971    0.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7988    1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0952    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0900   -0.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7884   -1.5091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4920   -0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2883   -5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0156   -5.9927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0519   -5.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 11  1  0
 16 17  2  0
 17  8  1  0
 13 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
  6 26  1  0
 26 27  2  0
 27  3  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3981517

   ---

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: 391.43

Molecular Weight (Monoisotopic): 391.1644

AlogP: 2.83

#Rotatable Bonds: 5

Polar Surface Area: 89.47

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.81

CX Basic pKa: 3.61

CX LogP: 1.73

CX LogD: 1.73

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.72

Np Likeness Score: -1.62

References

1.  (2016)  Piperidylpyrimidine derivatives as modulators of protein kinase inhibitors and of vascular endothelial growth factor receptor 2, 

Source

Source(1):

• BindingDB Database