(-)-(S)-3-tert-butyl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

ID: ALA1094113

Max Phase: Preclinical

Molecular Formula: C20H24N2O6

Molecular Weight: 388.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)C)[C@H]1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C20H24N2O6/c1-11-15(18(23)27-6)17(13-8-7-9-14(10-13)22(25)26)16(12(2)21-11)19(24)28-20(3,4)5/h7-10,17,21H,1-6H3/t17-/m0/s1

Standard InChI Key:  YXPRKGBMFPQBDH-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -1.9181   -4.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9193   -5.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2044   -5.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4880   -5.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4909   -4.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062   -4.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2041   -6.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9205   -7.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9227   -7.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2101   -8.3426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937   -7.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4899   -7.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388   -8.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2192   -8.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2251   -6.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9391   -7.1057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2262   -5.8673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6541   -6.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6339   -6.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -5.8653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3494   -7.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0628   -6.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7784   -7.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0606   -5.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7833   -6.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6311   -4.2252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462   -4.6366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6327   -3.3964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 11 14  1  0
  1  2  2  0
 12 15  1  0
  3  4  2  0
 15 16  1  0
 15 17  2  0
  4  5  1  0
 16 18  1  0
  2  3  1  0
  8 19  1  0
  5  6  2  0
 19 20  2  0
  7 12  1  0
 19 21  1  0
  8  9  2  0
 21 22  1  0
  9 10  1  0
 22 23  1  0
 10 11  1  0
 22 24  1  0
 11 12  2  0
 22 25  1  0
  7  3  1  1
  6  1  1  0
  9 13  1  0
 26 27  2  0
 26 28  1  0
  1 26  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1094113

   ---

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: 388.42

Molecular Weight (Monoisotopic): 388.1634

AlogP: 3.34

#Rotatable Bonds: 4

Polar Surface Area: 107.77

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.87

CX LogD: 2.87

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.48

Np Likeness Score: -0.84

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