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

ID: ALA4095440

PubChem CID: 132022591

Max Phase: Preclinical

Molecular Formula: C19H18N2O4S

Molecular Weight: 370.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1sc2cc(Oc3ccnc(C(=O)NC)c3)ccc2c1C

Standard InChI:  InChI=1S/C19H18N2O4S/c1-4-24-19(23)17-11(2)14-6-5-12(10-16(14)26-17)25-13-7-8-21-15(9-13)18(22)20-3/h5-10H,4H2,1-3H3,(H,20,22)

Standard InChI Key:  XGGWDJFVGDNYFQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.7311  -20.5896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3225  -21.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7311  -22.0160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5524  -22.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9651  -22.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5011  -21.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0169  -20.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2715  -19.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2355  -20.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5264  -20.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8173  -20.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8173  -21.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1041  -22.1241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3909  -21.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3909  -20.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777  -20.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9686  -20.8901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9686  -21.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2554  -22.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5463  -21.7114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5463  -20.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2554  -22.9455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777  -22.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5264  -22.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2355  -21.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0169  -21.9661    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
  4  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
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 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  1  0
 24 25  2  0
  9 25  1  0
 25 26  1  0
  6 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095440

   ---

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: 370.43

Molecular Weight (Monoisotopic): 370.0987

AlogP: 3.93

#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: 3.60

CX LogD: 3.60

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: -1.34

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