(1'S,4'S)-5'-Cyano-2',6'-dimethyl-4-phenyl-1',4'-dihydro-[3,4']bipyridinyl-3'-carboxylic acid ethyl ester

ID: ALA3392227

PubChem CID: 44318678

Max Phase: Preclinical

Molecular Formula: C22H21N3O2

Molecular Weight: 359.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(C)=C(C#N)[C@@H]1c1cnccc1-c1ccccc1

Standard InChI:  InChI=1S/C22H21N3O2/c1-4-27-22(26)20-15(3)25-14(2)18(12-23)21(20)19-13-24-11-10-17(19)16-8-6-5-7-9-16/h5-11,13,21,25H,4H2,1-3H3/t21-/m1/s1

Standard InChI Key:  KPTVIFYXSIIULZ-OAQYLSRUSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  1  0  0  0  0  0999 V2000
    3.5455   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2599   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9744   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2599   -2.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9744   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2599    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9744    0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5983   -1.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6913   -0.8870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310    0.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    1.3833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6889    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1165   -1.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6889   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9744    1.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2599    1.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6889   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4034    0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6876   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1178    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4034   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1178   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  2  0
  5  4  1  0
  6  5  1  0
  2  7  1  1
  8  1  1  0
  9  7  1  0
 10  3  1  0
 11 10  3  0
 12  8  2  0
 13 15  1  0
 14  9  1  0
 15  7  2  0
 16  8  1  0
 17  4  1  0
 18  6  1  0
 19  9  2  0
 20 13  2  0
 21 14  2  0
 22 14  1  0
 23 16  1  0
 24 23  1  0
 25 22  2  0
 26 21  1  0
 27 25  1  0
  6  3  2  0
 19 20  1  0
 27 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3392227

   ethyl (4S)-5-cyano-2,6-dimethyl-4-(4-phenylpyridin-3-yl)-1,4-dihydropyridine-3-carboxylate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 359.43

Molecular Weight (Monoisotopic): 359.1634

AlogP: 4.07

#Rotatable Bonds: 4

Polar Surface Area: 75.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.89

CX LogP: 2.51

CX LogD: 2.51

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.83

Np Likeness Score: -0.91

References

1. Straub A, Goehrt A, Born L.  (1997)  4-Biaryl-substituted dihydropyridines with an unusual antiperiplanar conformation,  7  (19): [10.1016/S0960-894X(97)10006-3]

Source

Source(1):

• Scientific Literature