Ethyl 7-{[2-(Methylcarbamoyl)pyridin-4-yl]oxy}-2-naphthoate

ID: ALA4073941

PubChem CID: 132022595

Max Phase: Preclinical

Molecular Formula: C20H18N2O4

Molecular Weight: 350.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc2ccc(Oc3ccnc(C(=O)NC)c3)cc2c1

Standard InChI:  InChI=1S/C20H18N2O4/c1-3-25-20(24)14-5-4-13-6-7-16(11-15(13)10-14)26-17-8-9-22-18(12-17)19(23)21-2/h4-12H,3H2,1-2H3,(H,21,23)

Standard InChI Key:  LUQVJGPRKZKUFB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   16.7665  -12.1100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0575  -12.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3484  -12.1100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6393  -12.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0575  -13.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7665  -13.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7665  -14.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4798  -14.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1889  -14.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1889  -13.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8979  -13.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6070  -13.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6070  -14.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3203  -14.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0293  -14.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7384  -14.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4475  -14.5698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1607  -14.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8698  -14.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7384  -15.7997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0293  -13.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3203  -13.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8979  -14.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0575  -14.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3484  -14.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3484  -13.7485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 16 20  2  0
 15 21  1  0
 21 22  2  0
 12 22  1  0
 13 23  2  0
  9 23  1  0
  7 24  2  0
 24 25  1  0
 25 26  2  0
  5 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4073941

   ---

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: 350.37

Molecular Weight (Monoisotopic): 350.1267

AlogP: 3.56

#Rotatable Bonds: 5

Polar Surface Area: 77.52

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 14.00

CX Basic pKa: 3.03

CX LogP: 3.07

CX LogD: 3.07

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: -0.64

References

1. Kim J, Jung YK, Kim C, Shin JS, Scheers E, Lee JY, Han SB, Lee CK, Neyts J, Ha JD, Jung YS..  (2017)  A Novel Series of Highly Potent Small Molecule Inhibitors of Rhinovirus Replication.,  60  (13): [PMID:28581749] [10.1021/acs.jmedchem.7b00175]

Source

Source(1):

• Scientific Literature