2,6-Bis-(2-imidazol-1-yl-ethyl)-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester: hydrochloride

ID: ALA1203662

Max Phase: Preclinical

Molecular Formula: C27H31ClN6O6

Molecular Weight: 534.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(CCn2ccnc2)N=C(CCn2ccnc2)/C(=C(/O)OCC)C1c1cccc([N+](=O)[O-])c1.Cl

Standard InChI:  InChI=1S/C27H30N6O6.ClH/c1-3-38-26(34)24-21(8-12-31-14-10-28-17-31)30-22(9-13-32-15-11-29-18-32)25(27(35)39-4-2)23(24)19-6-5-7-20(16-19)33(36)37;/h5-7,10-11,14-18,23,34H,3-4,8-9,12-13H2,1-2H3;1H/b26-24+;

Standard InChI Key:  SAUQRSISCISCEE-DVNIKIMTSA-N

Molfile:  

     RDKit          2D

 40 42  0  0  0  0  0  0  0  0999 V2000
    7.6969   -0.7643    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5517    0.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5554    1.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8054    3.2859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3382    2.9741    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
   -0.0031   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -5.2502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5205   -6.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570   -7.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5570   -7.5366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934   -6.1100    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
   -1.3070    5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471    5.8487    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  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 12  1  0
  9 17  1  0
 17 18  2  0
 18  6  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 21  1  0
  8 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
  7 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 31  1  0
 35 37  1  0
 37 38  2  0
 37 39  1  0
  5 40  1  0
M  CHG  2  37   1  39  -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: 534.57

Molecular Weight (Monoisotopic): 534.2227

AlogP: 4.33

#Rotatable Bonds: 12

Polar Surface Area: 146.90

Molecular Species: ACID

HBA: 11

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 5.27

CX Basic pKa: 6.85

CX LogP: 1.73

CX LogD: 1.46

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.16

Np Likeness Score: -0.90

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