N-(2-phenylimidazo[1,2-a]pyridin-3-yl)benzamide

ID: ALA379553

Cas Number: 171628-57-2

PubChem CID: 748028

Max Phase: Preclinical

Molecular Formula: C20H15N3O

Molecular Weight: 313.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1c(-c2ccccc2)nc2ccccn12)c1ccccc1

Standard InChI:  InChI=1S/C20H15N3O/c24-20(16-11-5-2-6-12-16)22-19-18(15-9-3-1-4-10-15)21-17-13-7-8-14-23(17)19/h1-14H,(H,22,24)

Standard InChI Key:  MFEAOWRPVOQOEV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   15.3913  -14.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5631  -15.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3488  -15.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9633  -14.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7869  -13.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0015  -13.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6036  -14.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4309  -13.2182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9908  -14.5785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2054  -14.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8716  -14.3236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5401  -14.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5404  -15.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8242  -16.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8244  -16.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5401  -17.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2570  -16.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2533  -16.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1257  -13.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9500  -13.5379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3601  -12.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9471  -12.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1197  -12.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7132  -12.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 19 11  2  0
 11 12  1  0
 12 10  2  0
  6  1  2  0
  1  2  1  0
 13 14  2  0
  3  4  1  0
 14 15  1  0
 15 16  2  0
  7  8  2  0
 16 17  1  0
  7  9  1  0
 17 18  2  0
 18 13  1  0
 12 13  1  0
  1  7  1  0
  4  5  2  0
 19 20  1  0
  9 10  1  0
 20 21  1  0
 10 20  1  0
 21 22  2  0
  2  3  2  0
 22 23  1  0
  5  6  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA379553

   N-(2-phenylimidazo[1,2-a]pyridin-3-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: 313.36

Molecular Weight (Monoisotopic): 313.1215

AlogP: 4.25

#Rotatable Bonds: 3

Polar Surface Area: 46.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.51

CX LogP: 3.97

CX LogD: 3.97

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -1.82

References

1. de Paulis T, Hemstapat K, Chen Y, Zhang Y, Saleh S, Alagille D, Baldwin RM, Tamagnan GD, Conn PJ..  (2006)  Substituent effects of N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides on positive allosteric modulation of the metabotropic glutamate-5 receptor in rat cortical astrocytes.,  49  (11): [PMID:16722652] [10.1021/jm051252j]

2. PubChem BioAssay data set, 

3. Rostrup F, Falk-Petersen CB, Harpso E K, Buchleithner S, Conforti I, Jung S, Gloriam DE, Schirmeister T, Wellendorph P, Fro Lund B..  (2021)  Structural Determinants for the Mode of Action of Imidazopyridine DS2 at δ-Containing γ-Aminobutyric Acid Type A Receptors.,  64  (8.0): [PMID:33847501] [10.1021/acs.jmedchem.0c02163]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays