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

ID: ALA4086772

PubChem CID: 132022550

Max Phase: Preclinical

Molecular Formula: C20H20N2O4S

Molecular Weight: 384.46

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  UOBQRNOVLWTGGC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   33.1171   -2.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7085   -2.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1171   -3.5756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9343   -3.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3429   -4.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3429   -2.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8914   -2.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4112   -2.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6618   -1.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6340   -2.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9249   -2.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2199   -2.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2199   -3.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5108   -3.6837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8018   -3.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8018   -2.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0927   -2.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3877   -2.4579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3877   -3.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6786   -3.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9737   -3.2751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9737   -2.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6786   -4.5009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0927   -3.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9249   -3.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6340   -3.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4112   -3.5256    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
  4  6  1  0
  2  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
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 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  1  0
 25 26  2  0
 10 26  1  0
 26 27  1  0
  7 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4086772

   ---

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: 14.00

CX Basic pKa: 3.02

CX LogP: 4.01

CX LogD: 4.01

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: -1.28

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]

2. Kim J, Shin JS, Ahn S, Han SB, Jung YS..  (2018)  3-Aryl-1,2,4-oxadiazole Derivatives Active Against Human Rhinovirus.,  9  (7): [PMID:30034598] [10.1021/acsmedchemlett.8b00134]

Source

Source(1):

• Scientific Literature