3-ethoxycarbonyl-4-(2-methoxyphenyl)-4H-pyridine-1-carboxylic acid phenyl ester

ID: ALA229468

PubChem CID: 44424118

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=CC1c1ccccc1OC

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

Standard InChI Key:  ARVLBNCGYZTGLR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.2432   -6.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9581   -6.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6745   -6.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716   -5.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9563   -5.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9579   -7.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403   -8.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2382   -8.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9507   -9.3488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6671   -8.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6709   -8.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9474  -10.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2312  -10.5834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6602  -10.5892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5184  -10.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5263   -9.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8144   -8.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0972   -9.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0966  -10.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8091  -10.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3863   -7.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0999   -8.1133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3882   -6.8742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5284   -6.8726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8143   -6.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8153   -7.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5288   -8.1165    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
  2 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:

   

   ALA229468

   3-O-ethyl 1-O-phenyl 4-(2-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: -0.13

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