Methyl 6-{[2-(Methylcarbamoyl)pyridin-4-yl]oxy}benzo[b]-thiophene-2-carboxylate

ID: ALA4087741

PubChem CID: 132022586

Max Phase: Preclinical

Molecular Formula: C17H14N2O4S

Molecular Weight: 342.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cc(Oc2ccc3cc(C(=O)OC)sc3c2)ccn1

Standard InChI:  InChI=1S/C17H14N2O4S/c1-18-16(20)13-8-12(5-6-19-13)23-11-4-3-10-7-15(17(21)22-2)24-14(10)9-11/h3-9H,1-2H3,(H,18,20)

Standard InChI Key:  SPSFDCBOADXEPG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   22.3498   -7.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9326   -8.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3325   -8.8637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9153   -9.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1114   -8.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6391   -7.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8532   -7.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1475   -7.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4352   -7.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4246   -8.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7082   -8.9176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0066   -8.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0130   -7.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3073   -7.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5950   -7.6619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5844   -8.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8680   -8.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1664   -8.4659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1770   -7.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8616   -9.7043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2902   -8.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1304   -8.9349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8468   -8.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6235   -8.7953    0.0000 S   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  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  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
 17 20  2  0
 16 21  2  0
 12 21  1  0
 10 22  1  0
 22 23  2  0
  7 23  1  0
 23 24  1  0
  5 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087741

   ---

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: 342.38

Molecular Weight (Monoisotopic): 342.0674

AlogP: 3.23

#Rotatable Bonds: 4

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: 2.73

CX LogD: 2.73

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: -1.20

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