US8796295, Table 2: Compound: 11

ID: ALA3694791

PubChem CID: 86766750

Max Phase: Preclinical

Molecular Formula: C17H13ClFN5O

Molecular Weight: 357.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(c1cncnc1)c1cc(C(=O)Nc2cccc(Cl)n2)ccc1F

Standard InChI:  InChI=1S/C17H13ClFN5O/c1-24(12-8-20-10-21-9-12)14-7-11(5-6-13(14)19)17(25)23-16-4-2-3-15(18)22-16/h2-10H,1H3,(H,22,23,25)

Standard InChI Key:  REEDXIZQVOCVDO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    3.6375   -0.9049    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 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
    2.5951   -3.0039    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
    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
    4.9329   -3.1621    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125   -5.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0507   -5.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0156   -7.4989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163   -8.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3216   -9.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6232  -10.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9196   -9.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9145   -8.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9517   -7.6351    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6129   -7.4931    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  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  2  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
 14 15  1  0
 11 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3694791

   N-(6-chloropyridin-2-yl)-4-fluoro-3-[methyl(pyrimidin-5-yl)amino]benzamide

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: 357.78

Molecular Weight (Monoisotopic): 357.0793

AlogP: 3.68

#Rotatable Bonds: 4

Polar Surface Area: 71.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.81

CX LogP: 3.15

CX LogD: 3.15

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.72

Np Likeness Score: -1.93

References

1.  (2014)  Substituted benzamide analogs as mGluR5 negative allosteric modulators and methods of making and using the same, 

Source

Source(1):

• BindingDB Database