N-(4-phenylpyridin-3-yl)-2-(tetrahydro-2H-pyran-4-carboxamido)isonicotinamide

ID: ALA5283804

Max Phase: Preclinical

Molecular Formula: C23H22N4O3

Molecular Weight: 402.45

Names and Identifiers

Canonical SMILES:  O=C(Nc1cnccc1-c1ccccc1)c1ccnc(NC(=O)C2CCOCC2)c1

Standard InChI:  InChI=1S/C23H22N4O3/c28-22(17-8-12-30-13-9-17)27-21-14-18(6-11-25-21)23(29)26-20-15-24-10-7-19(20)16-4-2-1-3-5-16/h1-7,10-11,14-15,17H,8-9,12-13H2,(H,26,29)(H,25,27,28)

Standard InChI Key:  IGJFKRWDBQKNRJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.0645    2.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0645    2.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7744    3.2845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876    2.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876    2.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3532    1.6434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3582    2.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3582    2.8756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0696    1.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4896    0.8183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4896    1.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7783    2.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7765   -0.4094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651   -0.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3537   -0.4094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3537   -2.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0651   -3.2845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7765   -2.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7765   -2.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7790    0.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0645    0.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0645   -0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7780   -0.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896   -0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896    0.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
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  6  5  1  0
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  8  9  2  0
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 11 10  2  0
 12 11  1  0
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 14 13  1  0
 15 14  2  0
 10 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 20 19  1  0
 21 20  1  0
 22 21  1  0
 23 22  1  0
 24 23  1  0
 19 24  1  0
 25  1  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283804

   ---

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: 402.45

Molecular Weight (Monoisotopic): 402.1692

AlogP: 3.76

#Rotatable Bonds: 5

Polar Surface Area: 93.21

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.94

CX Basic pKa: 4.63

CX LogP: 2.53

CX LogD: 2.53

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.68

Np Likeness Score: -1.27

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