Dimethyl 2,6-dimethyl-4-[3-(2-oxo-2-pyrrolidin-1-ylethoxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate

ID: ALA2237188

PubChem CID: 76308156

Max Phase: Preclinical

Molecular Formula: C23H28N2O6

Molecular Weight: 428.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(OCC(=O)N2CCCC2)c1

Standard InChI:  InChI=1S/C23H28N2O6/c1-14-19(22(27)29-3)21(20(15(2)24-14)23(28)30-4)16-8-7-9-17(12-16)31-13-18(26)25-10-5-6-11-25/h7-9,12,21,24H,5-6,10-11,13H2,1-4H3

Standard InChI Key:  UKMGSDPJTKKYJL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    7.2636  -14.3985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3726  -16.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5745  -12.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6489  -16.8964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9564  -15.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1231  -14.4451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2233  -16.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9966  -13.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8539  -13.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0828  -16.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6758  -15.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4264  -13.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7160  -12.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8203  -15.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5364  -15.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2503  -15.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9428  -16.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6892  -14.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1096  -15.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5266  -15.6262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5882  -11.9943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4128  -14.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3860  -15.6727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9831  -13.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8157  -15.6961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1469  -12.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2794  -13.2406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3535  -14.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1540  -14.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5755  -13.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0354  -12.9160    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
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2237188

   CID 76308156

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: 428.49

Molecular Weight (Monoisotopic): 428.1947

AlogP: 2.27

#Rotatable Bonds: 6

Polar Surface Area: 94.17

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: 1.24

CX LogD: 1.24

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.69

Np Likeness Score: -0.91

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