S-(Pyrimidin-2-yl)quinoline-2-carbothioate

ID: ALA5184362

PubChem CID: 168282541

Max Phase: Preclinical

Molecular Formula: C14H9N3OS

Molecular Weight: 267.31

Names and Identifiers

Canonical SMILES:  O=C(Sc1ncccn1)c1ccc2ccccc2n1

Standard InChI:  InChI=1S/C14H9N3OS/c18-13(19-14-15-8-3-9-16-14)12-7-6-10-4-1-2-5-11(10)17-12/h1-9H

Standard InChI Key:  PEKXORRZBWQMCT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    1.7853    1.0270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    0.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4964   -0.2163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2093    0.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2093    1.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003    1.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0723   -0.2045    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3637    0.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3637    1.0303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491   -0.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651    0.2225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7836   -0.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7836   -1.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491   -1.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947   -1.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2093   -1.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2093   -0.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947    0.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  1  6  1  0
  2  7  1  0
  8  7  1  0
  8  9  2  0
 10  8  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
 13 14  1  0
 10 15  1  0
 15 14  2  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5184362

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 267.31

Molecular Weight (Monoisotopic): 267.0466

AlogP: 2.96

#Rotatable Bonds: 2

Polar Surface Area: 55.74

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.57

CX LogP: 3.21

CX LogD: 3.21

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.53

Np Likeness Score: -1.18

References

1. Pillaiyar T, Flury P, Krüger N, Su H, Schäkel L, Barbosa Da Silva E, Eppler O, Kronenberger T, Nie T, Luedtke S, Rocha C, Sylvester K, Petry MRI, McKerrow JH, Poso A, Pöhlmann S, Gütschow M, O'Donoghue AJ, Xu Y, Müller CE, Laufer SA..  (2022)  Small-Molecule Thioesters as SARS-CoV-2 Main Protease Inhibitors: Enzyme Inhibition, Structure-Activity Relationships, Antiviral Activity, and X-ray Structure Determination.,  65  (13.0): [PMID:35709506] [10.1021/acs.jmedchem.2c00636]

Source

Source(1):

• Scientific Literature