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

ID: ALA5286581

Max Phase: Preclinical

Molecular Formula: C23H22N4O2

Molecular Weight: 386.46

Names and Identifiers

Canonical SMILES:  O=C(Nc1cncc(-c2ccccc2)c1)c1ccnc(NC(=O)C2CCCC2)c1

Standard InChI:  InChI=1S/C23H22N4O2/c28-22(17-8-4-5-9-17)27-21-13-18(10-11-25-21)23(29)26-20-12-19(14-24-15-20)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:  UFOSROJETSAJRO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    0.7141    1.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    1.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    2.6858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095    3.0947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226    2.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340    1.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340    0.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8474    0.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5544    0.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5544    1.4562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8456    1.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7117    1.4537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230    1.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230    2.6858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1344    1.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8431    1.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5544    1.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5544    0.6285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8413    0.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1344    0.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8413   -0.5990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1299   -1.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1299   -1.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7941   -2.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5404   -3.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7194   -3.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4657   -2.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185   -0.5990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  1  6  2  0
  7  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  7  2  0
 13  2  1  0
 14 13  1  0
 14 15  2  0
 16 14  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 16  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 25 24  1  0
 26 25  1  0
 27 26  1  0
 28 27  1  0
 28 24  1  0
 23 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286581

   ---

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: 3.97

CX LogP: 3.78

CX LogD: 3.78

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: -1.63

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