Ethyl 6-{[2-(Methylcarbamoyl)pyridin-4-yl]oxy}benzofuran-2-carboxylate

ID: ALA4090314

PubChem CID: 137643761

Max Phase: Preclinical

Molecular Formula: C18H16N2O5

Molecular Weight: 340.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2ccc(Oc3ccnc(C(=O)NC)c3)cc2o1

Standard InChI:  InChI=1S/C18H16N2O5/c1-3-23-18(22)16-8-11-4-5-12(10-15(11)25-16)24-13-6-7-20-14(9-13)17(21)19-2/h4-10H,3H2,1-2H3,(H,19,21)

Standard InChI Key:  FTCLUCPSNXWYDP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    4.3252  -10.7754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3252   -9.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6161   -9.5496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6161   -8.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0343   -9.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0343   -8.7324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7393   -8.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4484   -8.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4484   -9.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1575   -9.9582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8624   -9.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8624   -8.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5715   -8.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2806   -8.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2806   -9.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0578   -9.8043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5380   -9.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3552   -9.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7638   -8.4361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5810   -8.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9896   -7.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7638   -9.8501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0578   -8.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5715   -9.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7393   -9.9582    0.0000 C   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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  2  0
 17 23  2  0
 14 23  1  0
 15 24  2  0
 11 24  1  0
  9 25  2  0
  5 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090314

   ---

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: 340.34

Molecular Weight (Monoisotopic): 340.1059

AlogP: 3.16

#Rotatable Bonds: 5

Polar Surface Area: 90.66

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 14.00

CX Basic pKa: 3.02

CX LogP: 2.16

CX LogD: 2.16

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.72

Np Likeness Score: -0.70

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