2-(cyclopentanecarboxamido)-N-(4-phenylpyridin-3-yl)isonicotinamide

ID: ALA5280118

Max Phase: Preclinical

Molecular Formula: C23H22N4O2

Molecular Weight: 386.46

Names and Identifiers

Canonical SMILES:  O=C(Nc1cnccc1-c1ccccc1)c1ccnc(NC(=O)C2CCCC2)c1

Standard InChI:  InChI=1S/C23H22N4O2/c28-22(17-8-4-5-9-17)27-21-14-18(10-13-25-21)23(29)26-20-15-24-12-11-19(20)16-6-2-1-3-7-16/h1-3,6-7,10-15,17H,4-5,8-9H2,(H,26,29)(H,25,27,28)

Standard InChI Key:  XYTBUOHYMLZOLR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -1.7377   -2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0702   -1.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4027   -2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6577   -3.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4827   -3.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0702   -1.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850   -0.6019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850    0.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5016    0.6316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5016    1.4603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7868    1.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748    1.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599    1.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3549    1.4607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0697    1.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7876    1.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7876    0.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5016    0.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5016   -0.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7866   -1.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0697   -0.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0697    0.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4996    1.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4996    2.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830    3.1097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0697    2.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599    2.6988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748    0.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3554   -0.6019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  2  1  0
  7  6  1  0
  8  7  1  0
  9  8  2  0
 10  9  1  0
 11 10  2  0
 12 11  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 17 16  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
 16 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 15  2  0
 13 27  2  0
 28 12  2  0
  8 28  1  0
  6 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5280118

   ---

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: 386.46

Molecular Weight (Monoisotopic): 386.1743

AlogP: 4.52

#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: 4.63

CX LogP: 3.78

CX LogD: 3.78

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: -1.34

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