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

ID: ALA390507

PubChem CID: 44424115

Max Phase: Preclinical

Molecular Formula: C21H19NO4

Molecular Weight: 349.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1C1C=CN(C(=O)Oc2ccccc2)C=C1C(C)=O

Standard InChI:  InChI=1S/C21H19NO4/c1-15(23)19-14-22(21(24)26-16-8-4-3-5-9-16)13-12-17(19)18-10-6-7-11-20(18)25-2/h3-14,17H,1-2H3

Standard InChI Key:  NIAJTOOWNXPLHI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    5.3694    2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3682    1.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0831    1.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7995    1.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7966    2.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0813    2.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0829    0.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3653   -0.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3632   -0.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0757   -1.3530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7921   -0.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7959   -0.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0724   -2.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3562   -2.5876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7852   -2.5933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6434   -2.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6513   -1.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9394   -0.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2222   -1.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2216   -2.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9341   -2.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5113    0.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2249   -0.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5132    1.1216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6534    1.1232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9393    1.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
 10 13  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA390507

   phenyl 3-acetyl-4-(2-methoxyphenyl)-4H-pyridine-1-carboxylate

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: 349.39

Molecular Weight (Monoisotopic): 349.1314

AlogP: 4.28

#Rotatable Bonds: 4

Polar Surface Area: 55.84

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.60

CX LogD: 3.60

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.83

Np Likeness Score: 0.05

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