N-(4-(4-chlorophenyl)pyridin-3-yl)-2-(3,3-difluorocyclopentane-1-carboxamido)isonicotinamide

ID: ALA5286043

Max Phase: Preclinical

Molecular Formula: C23H19ClF2N4O2

Molecular Weight: 456.88

Names and Identifiers

Canonical SMILES:  O=C(Nc1cnccc1-c1ccc(Cl)cc1)c1ccnc(NC(=O)C2CCC(F)(F)C2)c1

Standard InChI:  InChI=1S/C23H19ClF2N4O2/c24-17-3-1-14(2-4-17)18-7-9-27-13-19(18)29-21(31)15-6-10-28-20(11-15)30-22(32)16-5-8-23(25,26)12-16/h1-4,6-7,9-11,13,16H,5,8,12H2,(H,29,31)(H,28,30,32)

Standard InChI Key:  HNRLJYOIIWONBJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.0646    0.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7791    1.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896    0.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896   -0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7780   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0646   -0.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7780   -1.4343    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7791    1.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0646    2.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0646    3.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7745    3.4923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4877    3.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4877    2.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3531    1.8512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581    2.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581    3.0834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0696    1.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7782    2.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4896    1.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4896    1.0260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7765    0.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0696    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7765   -0.2016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651   -0.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651   -1.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293   -1.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756   -2.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6545   -2.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4008   -1.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4415   -3.4923    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.1389   -2.9099    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3536   -0.2016    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
  5  7  1  0
  2  8  1  0
  9  8  1  0
 10  9  2  0
 11 10  1  0
 12 11  2  0
 13 12  1  0
  8 13  2  0
 14  9  1  0
 15 14  1  0
 15 16  2  0
 17 15  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 17  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 26 25  1  0
 27 26  1  0
 28 27  1  0
 29 28  1  0
 29 25  1  0
 28 30  1  0
 28 31  1  0
 24 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286043

   ---

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: 456.88

Molecular Weight (Monoisotopic): 456.1165

AlogP: 5.42

#Rotatable Bonds: 5

Polar Surface Area: 83.98

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.94

CX Basic pKa: 4.62

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: -1.12

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