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

ID: ALA3392230

PubChem CID: 44318909

Max Phase: Preclinical

Molecular Formula: C26H23N3O2

Molecular Weight: 409.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(C)=C(C#N)[C@@H]1c1cnccc1-c1ccc2ccccc2c1

Standard InChI:  InChI=1S/C26H23N3O2/c1-4-31-26(30)24-17(3)29-16(2)22(14-27)25(24)23-15-28-12-11-21(23)20-10-9-18-7-5-6-8-19(18)13-20/h5-13,15,25,29H,4H2,1-3H3/t25-/m1/s1

Standard InChI Key:  DRAFQLUUZHHPFJ-RUZDIDTESA-N

Molfile:  

     RDKit          2D

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    4.2599   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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
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    2.1165   -1.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    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
    7.8323   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5468   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5468    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8323    0.5583    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
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  2  7  1  1
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  9  7  2  0
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 24 23  1  0
 25 22  2  0
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  6  3  2  0
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 27 28  1  0
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 25 31  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3392230

   ethyl (4S)-5-cyano-2,6-dimethyl-4-(4-naphthalen-2-ylpyridin-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: 409.49

Molecular Weight (Monoisotopic): 409.1790

AlogP: 5.22

#Rotatable Bonds: 4

Polar Surface Area: 75.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.86

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.60

Np Likeness Score: -0.78

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