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

ID: ALA229414

PubChem CID: 44424116

Max Phase: Preclinical

Molecular Formula: C21H19NO4

Molecular Weight: 349.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2C=CN(C(=O)Oc3ccccc3)C=C2C(C)=O)cc1

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

Standard InChI Key:  QBGSYDWINNZPDS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   11.3944    1.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3932    1.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1081    0.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8245    1.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8216    1.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1063    2.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1079   -0.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3903   -0.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3882   -1.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1007   -1.7946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8171   -1.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8209   -0.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0974   -2.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3812   -3.0293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8102   -3.0350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6684   -2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6763   -1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9644   -1.3739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2472   -1.7836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2466   -2.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9591   -3.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5363   -0.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2499   -0.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5382    0.6800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1038    3.1586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3881    3.5690    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
  6 25  1  0
 11 12  2  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA229414

   phenyl 3-acetyl-4-(4-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: 0.10

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