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

ID: ALA4103195

PubChem CID: 132022547

Max Phase: Preclinical

Molecular Formula: C20H20N2O4S

Molecular Weight: 384.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H20N2O4S/c1-4-9-25-20(24)18-12(2)15-6-5-13(11-17(15)27-18)26-14-7-8-22-16(10-14)19(23)21-3/h5-8,10-11H,4,9H2,1-3H3,(H,21,23)

Standard InChI Key:  RSVLYWZYWVWMMB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   30.3579   -6.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1033   -7.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5834   -8.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4047   -8.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8133   -7.5419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6346   -7.5419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0474   -6.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8687   -6.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8133   -8.9642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1033   -8.9184    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.3178   -8.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6087   -9.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8996   -8.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1864   -9.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4773   -8.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7641   -9.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0550   -8.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0550   -7.8383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7641   -7.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7641   -6.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0550   -6.1957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3418   -6.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4773   -6.1957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4773   -7.8383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8996   -7.8383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6087   -7.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3178   -7.8383    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
  7  8  1  0
  4  9  2  0
  3 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 19 24  2  0
 15 24  1  0
 13 25  2  0
 25 26  1  0
 26 27  2  0
 11 27  1  0
  2 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103195

   ---

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: 384.46

Molecular Weight (Monoisotopic): 384.1144

AlogP: 4.32

#Rotatable Bonds: 6

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: 4.12

CX LogD: 4.12

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: -1.29

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