Cis-2-((1s,3s)-3-chlorocyclobutane-1-carboxamido)-N-(4-(4-chlorophenyl)pyridin-3-yl)isonicotinamide

ID: ALA5287592

Max Phase: Preclinical

Molecular Formula: C22H18Cl2N4O2

Molecular Weight: 441.32

Names and Identifiers

Canonical SMILES:  O=C(Nc1cnccc1-c1ccc(Cl)cc1)c1ccnc(NC(=O)[C@H]2C[C@@H](Cl)C2)c1

Standard InChI:  InChI=1S/C22H18Cl2N4O2/c23-16-3-1-13(2-4-16)18-6-7-25-12-19(18)27-21(29)14-5-8-26-20(11-14)28-22(30)15-9-17(24)10-15/h1-8,11-12,15,17H,9-10H2,(H,27,29)(H,26,28,30)/t15-,17+

Standard InChI Key:  FDHSBDWKFQRDCY-WOVMCDHWSA-N

Molfile:  

 
     RDKit          2D

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   -1.0597   -3.4744    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597   -2.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6530   -2.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0696   -1.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0696   -0.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7841   -0.2352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7841    0.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5002    0.9976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5002    1.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7858    2.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0741    1.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3597    2.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3546    1.8263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691    2.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7866    1.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4982    2.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4982    3.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7820    3.4744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691    3.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7866    0.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691    0.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691   -0.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856   -0.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002   -0.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    0.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856   -1.4731    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3597    3.0638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0741    1.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3551   -0.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4763   -2.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  1
  6  5  1  0
  7  6  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
 11 10  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 14  2  0
 20 15  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 20  2  0
 23 26  1  0
 12 27  2  0
 28 11  2  0
  7 28  1  0
  5 29  2  0
 30  4  1  0
  2 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287592

   ---

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: 441.32

Molecular Weight (Monoisotopic): 440.0807

AlogP: 5.01

#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: 3.91

CX LogD: 3.90

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.55

Np Likeness Score: -1.22

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