Methyl (4S)-(2-Chloro-4-fluorophenyl)-2-(chloromethyl)-5-cyano-6-methyl-1,4-dihydropyridine-3-carboxylate

ID: ALA1094801

Max Phase: Preclinical

Molecular Formula: C16H13Cl2FN2O2

Molecular Weight: 355.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(CCl)NC(C)=C(C#N)[C@@H]1c1ccc(F)cc1Cl

Standard InChI:  InChI=1S/C16H13Cl2FN2O2/c1-8-11(7-20)14(10-4-3-9(19)5-12(10)18)15(16(22)23-2)13(6-17)21-8/h3-5,14,21H,6H2,1-2H3/t14-/m0/s1

Standard InChI Key:  HXMHWKPUYLJIJN-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   11.7152  -23.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7141  -23.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4289  -24.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1453  -23.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1425  -23.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4271  -22.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4292  -25.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7129  -25.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7107  -26.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4232  -26.8509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1396  -26.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1435  -25.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9946  -26.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8526  -26.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8585  -25.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9995  -25.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0017  -24.3736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2839  -25.6092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5705  -25.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4246  -21.9039    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.5708  -24.7833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8605  -24.3799    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.2817  -26.4286    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  2  0
  7  3  1  1
  6  1  1  0
  9 13  1  0
  7  8  1  0
 11 14  1  0
  1  2  2  0
 12 15  1  0
  3  4  2  0
  8 16  1  0
 16 17  2  0
  4  5  1  0
 16 18  1  0
  2  3  1  0
 18 19  1  0
  5  6  2  0
  6 20  1  0
  7 12  1  0
 15 21  3  0
  8  9  2  0
  4 22  1  0
  9 10  1  0
 13 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094801

   ---

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: 355.20

Molecular Weight (Monoisotopic): 354.0338

AlogP: 3.63

#Rotatable Bonds: 3

Polar Surface Area: 62.12

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.78

CX LogD: 2.78

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.66

Np Likeness Score: -1.47

References

1. Arhancet GB, Woodard SS, Dietz JD, Garland DJ, Wagner GM, Iyanar K, Collins JT, Blinn JR, Numann RE, Hu X, Huang HC..  (2010)  Stereochemical requirements for the mineralocorticoid receptor antagonist activity of dihydropyridines.,  53  (10): [PMID:20408553] [10.1021/jm1002827]

Source

Source(1):

• Scientific Literature