3-Methyl-6-{[2-(methylcarbamoyl)pyridin-4-yl]oxy}benzo[b]-thiophene-2-carboxylic acid

ID: ALA4102246

PubChem CID: 137661966

Max Phase: Preclinical

Molecular Formula: C17H14N2O4S

Molecular Weight: 342.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cc(Oc2ccc3c(C)c(C(=O)O)sc3c2)ccn1

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

Standard InChI Key:  XCSKTXCDBUWOSU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    7.1816   -2.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9311   -3.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4112   -4.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2284   -4.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6370   -4.9237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6370   -3.5096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9311   -4.8779    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.1538   -4.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447   -5.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7398   -4.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0307   -5.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216   -4.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6166   -5.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9075   -4.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9075   -3.8060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6166   -3.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6166   -2.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9075   -2.1716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1985   -2.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216   -2.1716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216   -3.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7398   -3.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447   -3.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1538   -3.8060    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
  4  6  2  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  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  2  0
 22 23  1  0
 23 24  2  0
  8 24  1  0
  2 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4102246

   ---

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: 3.45

#Rotatable Bonds: 4

Polar Surface Area: 88.52

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.40

CX Basic pKa: 2.78

CX LogP: 2.37

CX LogD: -0.56

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.76

Np Likeness Score: -1.16

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