3-ethoxycarbonyl-4-(4-methoxyphenyl)-4H-pyridine-1-carboxylic acid phenyl ester

ID: ALA229130

PubChem CID: 23661654

Max Phase: Preclinical

Molecular Formula: C22H21NO5

Molecular Weight: 379.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=CN(C(=O)Oc2ccccc2)C=CC1c1ccc(OC)cc1

Standard InChI:  InChI=1S/C22H21NO5/c1-3-27-21(24)20-15-23(22(25)28-18-7-5-4-6-8-18)14-13-19(20)16-9-11-17(26-2)12-10-16/h4-15,19H,3H2,1-2H3

Standard InChI Key:  VGWUGLWTKLFQCP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.7724   -6.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4872   -7.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2037   -6.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2008   -6.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4854   -5.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4870   -8.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7695   -8.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7673   -9.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4799   -9.8113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1963   -9.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2001   -8.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4765  -10.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7604  -11.0459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1893  -11.0517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0476  -10.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0555   -9.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3435   -9.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6264   -9.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6257  -10.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3383  -11.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9155   -8.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6291   -8.5758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9174   -7.3367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4830   -4.8580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7673   -4.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3444   -8.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0580   -8.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 13 14  1  0
  7  3  1  0
 13 15  2  0
  7  8  1  0
 14 16  1  0
  3  4  2  0
 16 17  2  0
 17 18  1  0
  4  5  1  0
 18 19  2  0
  2  3  1  0
 19 20  1  0
  5  6  2  0
 20 21  2  0
 21 16  1  0
  7 12  1  0
 12 22  1  0
  8  9  2  0
 22 23  1  0
  9 10  1  0
 22 24  2  0
 10 11  1  0
  6 25  1  0
 11 12  2  0
 25 26  1  0
  6  1  1  0
 23 27  1  0
 10 13  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA229130

   3-O-ethyl 1-O-phenyl 4-(4-methoxyphenyl)-4H-pyridine-1,3-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: 379.41

Molecular Weight (Monoisotopic): 379.1420

AlogP: 4.25

#Rotatable Bonds: 5

Polar Surface Area: 65.07

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.00

CX LogD: 4.00

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.73

Np Likeness Score: -0.09

References

1. Voigt B, Coburger C, Monár J, Hilgeroth A..  (2007)  Structure-activity relationships of novel N-acyloxy-1,4-dihydropyridines as P-glycoprotein inhibitors.,  15  (15): [PMID:17533131] [10.1016/j.bmc.2007.05.036]

Source

Source(1):

• Scientific Literature