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

ID: ALA4100479

PubChem CID: 137660969

Max Phase: Preclinical

Molecular Formula: C20H20N2O4S

Molecular Weight: 384.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1ccc(Oc2ccc3c(C)c(C(=O)OC(C)C)sc3c2)cn1

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

Standard InChI Key:  XLZNHZBIZBJAJV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.7311   -3.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1397   -4.5946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9610   -4.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3737   -5.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3737   -3.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9097   -3.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4255   -3.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6801   -2.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6441   -3.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9350   -3.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2259   -3.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2259   -4.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5127   -4.7027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7995   -4.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7995   -3.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0863   -3.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772   -3.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6640   -3.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9549   -3.4728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9549   -4.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6640   -2.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772   -4.2941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0863   -4.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9350   -4.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6441   -4.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4255   -4.5488    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  3  4  1  0
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  7 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100479

   ---

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: 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: ┄

CX Basic pKa: 1.43

CX LogP: 4.01

CX LogD: 4.01

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: -1.41

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