N-(2-chlorophenyl)-6-(4-hydroxypiperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

ID: ALA1077740

PubChem CID: 46175114

Max Phase: Preclinical

Molecular Formula: C19H19ClN4O2

Molecular Weight: 370.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccccc1Cl)c1cnc2ccc(C3(O)CCNCC3)cn12

Standard InChI:  InChI=1S/C19H19ClN4O2/c20-14-3-1-2-4-15(14)23-18(25)16-11-22-17-6-5-13(12-24(16)17)19(26)7-9-21-10-8-19/h1-6,11-12,21,26H,7-10H2,(H,23,25)

Standard InChI Key:  NFPDLYRGXRIUTG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   10.7819  -26.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7807  -27.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4956  -27.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4937  -26.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2091  -26.6172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2140  -27.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0015  -27.6944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4834  -27.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9936  -26.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0107  -25.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7325  -25.1348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3038  -25.1088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3188  -24.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0453  -23.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0606  -23.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3555  -22.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6290  -23.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6172  -23.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8966  -24.2659    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.0681  -26.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0698  -25.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3594  -24.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6426  -25.3796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6408  -26.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3558  -26.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4750  -25.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
 12 13  1  0
  3  6  1  0
 13 14  2  0
  1  2  1  0
 14 15  1  0
  5  4  1  0
 15 16  2  0
  6  7  2  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
 18 13  1  0
  8  9  2  0
 18 19  1  0
 20 21  1  0
  9  5  1  0
  4  1  2  0
  9 10  1  0
  5  6  1  0
 10 11  2  0
 20 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  1 20  1  0
 10 12  1  0
 20 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1077740

   N-(2-chlorophenyl)-6-(4-hydroxypiperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

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: 370.84

Molecular Weight (Monoisotopic): 370.1197

AlogP: 2.81

#Rotatable Bonds: 3

Polar Surface Area: 78.66

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.81

CX Basic pKa: 9.37

CX LogP: 1.18

CX LogD: -0.78

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: -1.18

References

1. Qiao L, Choi S, Case A, Gainer TG, Seyb K, Glicksman MA, Lo DC, Stein RL, Cuny GD..  (2009)  Structure-activity relationship study of EphB3 receptor tyrosine kinase inhibitors.,  19  (21): [PMID:19783434] [10.1016/j.bmcl.2009.09.010]

Source

Source(1):

• Scientific Literature