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

ID: ALA4087372

PubChem CID: 132022549

Max Phase: Preclinical

Molecular Formula: C18H16N2O4S

Molecular Weight: 356.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2ccc(Oc3ccnc(C(=O)NC)c3)cc2s1

Standard InChI:  InChI=1S/C18H16N2O4S/c1-3-23-18(22)16-8-11-4-5-12(10-15(11)25-16)24-13-6-7-20-14(9-13)17(21)19-2/h4-10H,3H2,1-2H3,(H,19,21)

Standard InChI Key:  OAYUWIIWAAZTII-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   11.1548  -14.4168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7490  -15.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1686  -15.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9857  -15.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4054  -16.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9319  -15.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4415  -14.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6641  -14.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9487  -14.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2460  -14.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2547  -15.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5479  -15.9942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8325  -15.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8238  -14.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1084  -14.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4058  -14.7852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4144  -15.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076  -16.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922  -15.6203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9836  -14.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7163  -16.8432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1257  -16.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9660  -15.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6727  -15.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4538  -15.8074    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
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 17 22  2  0
 13 22  1  0
 11 23  1  0
 23 24  2  0
  8 24  1  0
 24 25  1  0
  6 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087372

   ---

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: 356.40

Molecular Weight (Monoisotopic): 356.0831

AlogP: 3.62

#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: 3.08

CX LogD: 3.08

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: -1.27

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