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

ID: ALA3392229

PubChem CID: 44318895

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-c1cccc2ccccc12

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

Standard InChI Key:  PFMILRPAGKLHTO-RUZDIDTESA-N

Molfile:  

     RDKit          2D

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    9.3323    0.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3323   -0.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9034    0.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9034   -0.2160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0468    1.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6178   -0.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7612    0.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7612   -0.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6178    1.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7087   -0.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3323    2.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7612    2.2590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9034    2.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6178   -1.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4757    1.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1902   -0.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0468   -1.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4757    1.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7612   -1.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1902   -1.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9034    3.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9047   -0.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1889    3.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9047   -1.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 24 20  2  0
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  3  7  2  0
 22 25  2  0
 16 26  2  0
 31 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3392229

   ethyl (4S)-5-cyano-2,6-dimethyl-4-(4-naphthalen-1-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: 4.73

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.60

Np Likeness Score: -0.89

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