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

ID: ALA229413

PubChem CID: 44424114

Max Phase: Preclinical

Molecular Formula: C21H19NO3

Molecular Weight: 333.39

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H19NO3/c1-15-8-10-17(11-9-15)19-12-13-22(14-20(19)16(2)23)21(24)25-18-6-4-3-5-7-18/h3-14,19H,1-2H3

Standard InChI Key:  LBGLHYRKPNFBJA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -1.8723    1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734    0.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4422    0.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4450    1.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1604    2.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1588   -0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8763   -0.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8785   -1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1660   -2.0113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4496   -1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4457   -0.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1693   -2.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854   -3.2459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4565   -3.2517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -2.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5903   -2.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3023   -1.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0194   -2.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201   -2.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3075   -3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2697   -0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9832   -0.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2715    0.4633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1629    2.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  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
  6 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA229413

   phenyl 3-acetyl-4-(4-methylphenyl)-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: 333.39

Molecular Weight (Monoisotopic): 333.1365

AlogP: 4.58

#Rotatable Bonds: 3

Polar Surface Area: 46.61

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.27

CX LogD: 4.27

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -0.02

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