US8796295, Table 2: Compound: 14

ID: ALA3694792

PubChem CID: 69937130

Max Phase: Preclinical

Molecular Formula: C16H12FN5O2

Molecular Weight: 325.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccnc(NC(=O)c2cc(F)cc(Oc3cncnc3)c2)n1

Standard InChI:  InChI=1S/C16H12FN5O2/c1-10-2-3-20-16(21-10)22-15(23)11-4-12(17)6-13(5-11)24-14-7-18-9-19-8-14/h2-9H,1H3,(H,20,21,22,23)

Standard InChI Key:  GCQMRMPNHPBXIY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    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 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
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 N   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
   -1.5548   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934   -5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1924   -6.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1923   -7.2071    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4914   -5.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4915   -3.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7897   -3.0041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7876   -1.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0841   -0.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0789    0.7513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7773    1.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4808    0.7424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4860   -0.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925   -3.0071    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  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 15 23  2  0
 23 10  1  0
  6 24  2  0
 24  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3694792

   3-fluoro-N-(4-methylpyrimidin-2-yl)-5-pyrimidin-5-yloxybenzamide

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: 325.30

Molecular Weight (Monoisotopic): 325.0975

AlogP: 2.76

#Rotatable Bonds: 4

Polar Surface Area: 89.89

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.05

CX Basic pKa: 1.27

CX LogP: 1.67

CX LogD: 1.67

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: -1.84

References

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

Source

Source(1):

• BindingDB Database