2-(cyclobutanecarboxamido)-N-(5-phenylpyridin-3-yl)isonicotinamide

ID: ALA5287294

Max Phase: Preclinical

Molecular Formula: C22H20N4O2

Molecular Weight: 372.43

Names and Identifiers

Canonical SMILES:  O=C(Nc1cncc(-c2ccccc2)c1)c1ccnc(NC(=O)C2CCC2)c1

Standard InChI:  InChI=1S/C22H20N4O2/c27-21(16-7-4-8-16)26-20-12-17(9-10-24-20)22(28)25-19-11-18(13-23-14-19)15-5-2-1-3-6-15/h1-3,5-6,9-14,16H,4,7-8H2,(H,25,28)(H,24,26,27)

Standard InChI Key:  DZDZSVFHIFHEGW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -1.4292    2.0629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148    0.8254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    2.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125    2.4736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287    2.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287    1.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171    0.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432    0.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596   -0.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697    0.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    1.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436    0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535   -0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697   -0.0031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8553    1.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535   -1.2361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1391   -1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -1.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075   -0.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4105   -0.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6276   -1.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1391   -2.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  5  4  2  0
  6  5  1  0
  7  6  2  0
  8  7  1  0
  9  8  2  0
  4  9  1  0
 10  8  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 10  2  0
 16  2  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
 16 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 25 24  1  0
 26 25  1  0
 26 27  1  0
 27 24  1  0
 23 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287294

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 372.43

Molecular Weight (Monoisotopic): 372.1586

AlogP: 4.13

#Rotatable Bonds: 5

Polar Surface Area: 83.98

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.95

CX Basic pKa: 3.97

CX LogP: 3.33

CX LogD: 3.33

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.71

Np Likeness Score: -1.67

References

1. Luo G, Chen L, Jacutin-Porte S, Han Y, Burton CR, Xiao H, Krause CM, Cao Y, Liu N, Kish K, Lewis HA, Macor JE, Dubowchik GM..  (2023)  Structure-activity relationship (SAR) studies on substituted N-(pyridin-3-yl)-2-amino-isonicotinamides as highly potent and selective glycogen synthase kinase-3 (GSK-3) inhibitors.,  81  [PMID:36669575] [10.1016/j.bmcl.2023.129143]

Source

Source(1):

• Scientific Literature