US8796295, Table 2: Compound: 9

ID: ALA3694789

PubChem CID: 86654696

Max Phase: Preclinical

Molecular Formula: C16H14FN5OS

Molecular Weight: 343.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1csc(NC(=O)c2cc(F)cc(N(C)c3cncnc3)c2)n1

Standard InChI:  InChI=1S/C16H14FN5OS/c1-10-8-24-16(20-10)21-15(23)11-3-12(17)5-13(4-11)22(2)14-6-18-9-19-7-14/h3-9H,1-2H3,(H,20,21,23)

Standard InChI Key:  JHFMVNJTXHIDIX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  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
    3.8915   -3.7585    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
    4.9235   -5.8621    0.0000 F   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
    1.2883   -5.2495    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
   -0.0156   -5.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0218   -7.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3117   -5.2360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6155   -5.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9648   -5.3535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9723   -6.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1653   -6.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2268   -7.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7585   -7.4596    0.0000 S   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  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15  9  1  0
 14 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  1  0
 21 23  2  0
 23 24  1  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3694789

   3-fluoro-5-(methyl(pyrimidin-5-yl)amino)-N-(4-methylthiazol-2-yl)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: 343.39

Molecular Weight (Monoisotopic): 343.0903

AlogP: 3.40

#Rotatable Bonds: 4

Polar Surface Area: 71.01

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.87

CX Basic pKa: 1.83

CX LogP: 2.42

CX LogD: 2.42

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: -2.45

References

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

Source

Source(1):

• BindingDB Database