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

ID: ALA4099621

PubChem CID: 137658814

Max Phase: Preclinical

Molecular Formula: C18H17N3O4S

Molecular Weight: 371.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1sc2cc(Oc3ccnc(C(=O)NC)c3)ccc2c1N

Standard InChI:  InChI=1S/C18H17N3O4S/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,3,19H2,1-2H3,(H,20,22)

Standard InChI Key:  UZJQWGMDMLSEQH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    7.9959  -19.7948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7412  -20.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2214  -21.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0427  -21.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4554  -20.5303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2767  -20.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6853  -19.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4554  -21.9526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7412  -21.9068    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.9599  -21.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2508  -22.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5376  -21.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8244  -22.0607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1112  -21.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4021  -22.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6930  -21.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6930  -20.8267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4021  -20.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4021  -19.5968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6930  -19.1840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839  -19.5968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1112  -19.1840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1112  -20.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5376  -20.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2508  -20.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9599  -20.8267    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:

   

   ALA4099621

   ---

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: 371.42

Molecular Weight (Monoisotopic): 371.0940

AlogP: 3.21

#Rotatable Bonds: 5

Polar Surface Area: 103.54

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 14.00

CX Basic pKa: 3.02

CX LogP: 2.91

CX LogD: 2.91

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.67

Np Likeness Score: -1.23

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