4-[2-(Ethylcarbamoyl)-3-methylbenzo[b]thiophen-6-yloxy]-N-methylpicolinamide

ID: ALA4091888

PubChem CID: 137653911

Max Phase: Preclinical

Molecular Formula: C19H19N3O3S

Molecular Weight: 369.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H19N3O3S/c1-4-21-19(24)17-11(2)14-6-5-12(10-16(14)26-17)25-13-7-8-22-15(9-13)18(23)20-3/h5-10H,4H2,1-3H3,(H,20,23)(H,21,24)

Standard InChI Key:  UFZTWLZOSIYMDU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    9.5796   -9.2315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1710   -9.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5796  -10.6497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3968  -10.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8053  -11.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3538   -9.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8736   -9.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1242   -8.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0964   -9.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3873   -9.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6824   -9.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6824  -10.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9733  -10.7578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2642  -10.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2642   -9.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5551   -9.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8501   -9.5320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8501  -10.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1410  -10.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4361  -10.3492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4361   -9.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1410  -11.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5551  -10.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3873  -10.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0964  -10.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8736  -10.5997    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
 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  1  0
 24 25  2  0
  9 25  1  0
 25 26  1  0
  6 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091888

   ---

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: 369.45

Molecular Weight (Monoisotopic): 369.1147

AlogP: 3.51

#Rotatable Bonds: 5

Polar Surface Area: 80.32

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.97

CX Basic pKa: 3.02

CX LogP: 2.67

CX LogD: 2.67

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -1.45

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