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

ID: ALA2237187

PubChem CID: 60168017

Max Phase: Preclinical

Molecular Formula: C23H28N2O7

Molecular Weight: 444.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(OCC(=O)N2CCOCC2)c1

Standard InChI:  InChI=1S/C23H28N2O7/c1-14-19(22(27)29-3)21(20(15(2)24-14)23(28)30-4)16-6-5-7-17(12-16)32-13-18(26)25-8-10-31-11-9-25/h5-7,12,21,24H,8-11,13H2,1-4H3

Standard InChI Key:  IKPYXJXNSBBTRD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   11.4363  -10.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5452  -13.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7472   -9.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8216  -13.4163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1289  -12.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2957  -10.9650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3960  -13.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1692   -9.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0266   -9.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2555  -13.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8485  -11.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5990   -9.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8887   -9.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9929  -11.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7091  -11.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4229  -11.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1155  -12.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8619  -10.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2823  -11.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6993  -12.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7608   -8.5142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5855  -10.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5586  -12.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1558  -10.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9884  -12.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3196   -9.3154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4521   -9.7606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4354  -10.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1363  -11.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8560  -10.6069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8706   -9.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1653   -9.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 18  1  0
  2  4  1  0
 19 25  1  0
 12 26  1  0
 24  8  2  0
 11 23  1  0
  5 16  1  0
 17  7  1  0
 16 20  1  0
 17  4  1  0
 13 12  2  0
 26  9  1  0
 12 22  1  0
 20 14  1  0
  9  3  1  0
 18 24  1  0
  2 10  1  0
 25 15  1  0
  3 21  2  0
 16  1  2  0
 23  2  2  0
 18 22  2  0
  5 11  1  0
 17  5  2  0
 19  6  2  0
 23 19  1  0
  8 13  1  0
  3 27  1  0
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2237187

   CID 60168017

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: 444.48

Molecular Weight (Monoisotopic): 444.1897

AlogP: 1.50

#Rotatable Bonds: 6

Polar Surface Area: 103.40

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.62

CX LogD: 0.62

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.66

Np Likeness Score: -1.07

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