2-(3,3-difluorocyclopentane-1-carboxamido)-N-(5-(2,3-difluorophenyl)pyridin-3-yl)isonicotinamide

ID: ALA5269369

Max Phase: Preclinical

Molecular Formula: C23H18F4N4O2

Molecular Weight: 458.42

Names and Identifiers

Canonical SMILES:  O=C(Nc1cncc(-c2cccc(F)c2F)c1)c1ccnc(NC(=O)C2CCC(F)(F)C2)c1

Standard InChI:  InChI=1S/C23H18F4N4O2/c24-18-3-1-2-17(20(18)25)15-8-16(12-28-11-15)30-21(32)13-5-7-29-19(9-13)31-22(33)14-4-6-23(26,27)10-14/h1-3,5,7-9,11-12,14H,4,6,10H2,(H,30,32)(H,29,31,33)

Standard InChI Key:  JAZBHABYAFZEPR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -1.7268   -2.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7268   -3.5213    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5514   -2.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1391   -0.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8536   -0.1883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8536    0.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437    1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437    1.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1433    1.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    0.6343    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5698    1.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5698    1.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8597   -0.1862    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    3.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126    3.5213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    3.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292    3.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8554    2.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5698    1.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5698    1.0445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.1883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -1.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
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  9 10  1  0
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 15 16  2  0
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 23 17  2  0
 20 24  1  0
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 25 26  2  0
 26 27  1  0
 27 14  2  0
 12 28  2  0
 11 29  1  0
 29 30  2  0
 30 31  1  0
 31  9  2  0
  7 32  2  0
 33  6  1  0
 33  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5269369

   ---

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: 458.42

Molecular Weight (Monoisotopic): 458.1366

AlogP: 5.05

#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: 3.76

CX LogP: 3.55

CX LogD: 3.55

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.52

Np Likeness Score: -1.42

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