Ethyl 3-Chloro-6-{[2-(methylcarbamoyl)pyridin-4-yl]oxy}benzo-[b]thiophene-2-carboxylate

ID: ALA4073774

PubChem CID: 132022587

Max Phase: Preclinical

Molecular Formula: C18H15ClN2O4S

Molecular Weight: 390.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1sc2cc(Oc3ccnc(C(=O)NC)c3)ccc2c1Cl

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

Standard InChI Key:  NRRZTDPBZBYSQB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   18.7556   -9.1011    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.5009   -9.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9811  -10.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8024  -10.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2151   -9.8367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0364   -9.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4450   -9.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2151  -11.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5009  -11.2132    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.7196  -10.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0105  -11.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2973  -10.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5841  -11.3671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8708  -10.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1617  -11.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4527  -10.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4527  -10.1330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1617   -9.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1617   -8.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4527   -8.4904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7436   -8.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8708   -8.4904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8708  -10.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2973  -10.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0105   -9.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7196  -10.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  2  0
  3  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 18 23  2  0
 14 23  1  0
 12 24  2  0
 24 25  1  0
 25 26  2  0
 10 26  1  0
  2 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4073774

   ---

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: 14.00

CX Basic pKa: 3.02

CX LogP: 3.69

CX LogD: 3.69

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: -1.45

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