2-Imidazol-1-ylmethyl-6-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-ethyl ester 3-methyl ester: hydrochloride

ID: ALA1203626

Max Phase: Preclinical

Molecular Formula: C21H23ClN4O6

Molecular Weight: 426.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCO/C(O)=C1\C(C)=NC(Cn2ccnc2)=C(C(=O)OC)C1c1cccc([N+](=O)[O-])c1.Cl

Standard InChI:  InChI=1S/C21H22N4O6.ClH/c1-4-31-21(27)17-13(2)23-16(11-24-9-8-22-12-24)19(20(26)30-3)18(17)14-6-5-7-15(10-14)25(28)29;/h5-10,12,18,27H,4,11H2,1-3H3;1H/b21-17+;

Standard InChI Key:  HJRUVIXVMHLWIA-DIRYEVLESA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
    7.6969    0.3751    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8916   -4.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2526    1.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2524    0.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4979   -1.0529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0317   -0.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0351    3.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3064    4.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991    0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969    1.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945    3.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943    3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5964    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8888    5.2533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8478    5.8502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9260    5.8568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
  9 16  1  0
 16 17  2  0
 17  6  1  0
 17 18  1  0
  8 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
  7 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 27 29  1  0
 29 30  2  0
 29 31  1  0
  5 32  1  0
M  CHG  2  29   1  31  -1
M  END

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: 426.43

Molecular Weight (Monoisotopic): 426.1539

AlogP: 3.28

#Rotatable Bonds: 7

Polar Surface Area: 129.08

Molecular Species: ACID

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.30

CX Basic pKa: 6.76

CX LogP: 1.66

CX LogD: 0.97

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: -1.18

References

1. Archibald JL, Bradley G, Opalko A, Ward TJ, White JC, Ennis C, Shepperson NB..  (1990)  Design of an antithrombotic-antihypertensive agent (Wy 27569). Synthesis and evaluation of a series of 2-heteroaryl-substituted dihydropyridines.,  33  (2): [PMID:2299629] [10.1021/jm00164a028]

Source

Source(1):

• Scientific Literature