Ethyl 7-Chloro-6-{[2-(methylcarbamoyl)pyridin-4-yl]oxy}benzo-[b]thiophene-2-carboxylate

ID: ALA4100582

PubChem CID: 132022551

Max Phase: Preclinical

Molecular Formula: C18H15ClN2O4S

Molecular Weight: 390.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2ccc(Oc3ccnc(C(=O)NC)c3)c(Cl)c2s1

Standard InChI:  InChI=1S/C18H15ClN2O4S/c1-3-24-18(23)14-8-10-4-5-13(15(19)16(10)26-14)25-11-6-7-21-12(9-11)17(22)20-2/h4-9H,3H2,1-2H3,(H,20,22)

Standard InChI Key:  ZQTXOVPILJZEBZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   13.1575  -16.9745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1575  -16.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4484  -15.7487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4484  -14.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8666  -15.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8666  -14.9315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5716  -14.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2806  -14.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2806  -15.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9897  -16.1573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6947  -15.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6947  -14.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4038  -14.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1129  -14.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1129  -15.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8901  -16.0034    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.3702  -15.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1874  -15.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5960  -14.6352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4132  -14.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8218  -13.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5960  -16.0492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8901  -14.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4038  -16.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4038  -16.9745    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.5716  -16.1573    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
 24 25  1  0
  9 26  2  0
  5 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100582

   ---

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: 390.85

Molecular Weight (Monoisotopic): 390.0441

AlogP: 4.28

#Rotatable Bonds: 5

Polar Surface Area: 77.52

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.99

CX Basic pKa: 2.99

CX LogP: 3.69

CX LogD: 3.69

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: -1.09

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