Dimethyl 4-[3-(2-methoxy-2-oxoethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-di-carboxylate

ID: ALA2237186

PubChem CID: 76333489

Max Phase: Preclinical

Molecular Formula: C20H23NO7

Molecular Weight: 389.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)COc1cccc(C2C(C(=O)OC)=C(C)NC(C)=C2C(=O)OC)c1

Standard InChI:  InChI=1S/C20H23NO7/c1-11-16(19(23)26-4)18(17(12(2)21-11)20(24)27-5)13-7-6-8-14(9-13)28-10-15(22)25-3/h6-9,18,21H,10H2,1-5H3

Standard InChI Key:  LGENXUGEIZHYQB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    3.8957   -7.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9090   -7.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -6.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3359   -7.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3225   -7.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6024   -8.3427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2023   -6.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2157   -5.8447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4780   -7.0705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0602   -6.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0735   -5.8910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7668   -7.1400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0334   -8.3659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1756   -8.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6425   -5.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9358   -5.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9492   -4.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6693   -4.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3759   -4.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3626   -5.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7710   -6.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4882   -6.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0972   -4.2413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8049   -4.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5261   -4.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2338   -4.6892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5397   -3.4398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9551   -4.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  1  0
  7  8  2  0
  7  9  1  0
  2  7  1  0
 10 11  2  0
 10 12  1  0
  4 10  1  0
  5 13  1  0
  1 14  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
  3 15  1  0
  9 21  1  0
 12 22  1  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2237186

   Dimethyl 4-[3-(2-methoxy-2-oxoethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

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: 389.40

Molecular Weight (Monoisotopic): 389.1475

AlogP: 1.82

#Rotatable Bonds: 6

Polar Surface Area: 100.16

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.34

CX LogD: 1.34

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -0.64

References

1. Bansal R, Jain P, Calle C, Carron R, Pemberton K, Harvey AL.  (2012)  Synthesis of a New Series of 4-Aryl-1,4-Dihydropyridines with Calcium Channel Blocking and Vasodilatory Activity,  21  (6): [10.1007/s00044-011-9600-x]

Source

Source(1):

• Scientific Literature