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

ID: ALA4071055

PubChem CID: 137639520

Max Phase: Preclinical

Molecular Formula: C19H19N3O3S

Molecular Weight: 369.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cc(Oc2ccc3c(C)c(C(=O)N(C)C)sc3c2)ccn1

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

Standard InChI Key:  QNUYGPGVKXCNRI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    9.6628  -14.5391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2501  -15.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6628  -15.9655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2501  -16.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4841  -15.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4287  -15.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9486  -14.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2033  -13.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1672  -14.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4582  -14.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7449  -14.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7449  -15.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0317  -16.0736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3185  -15.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3185  -14.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6094  -14.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8962  -14.8396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8962  -15.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912  -16.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4780  -15.6609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4780  -14.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912  -16.8949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6094  -16.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4582  -16.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1672  -15.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9486  -15.9156    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
  3  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:

   

   ALA4071055

   ---

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: 3.46

#Rotatable Bonds: 4

Polar Surface Area: 71.53

Molecular Species: NEUTRAL

HBA: 5

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: 2.54

CX LogD: 2.54

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.76

Np Likeness Score: -1.50

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