S-(Pyrimidin-2-yl)-5-(4-bromophenyl)thiophene-2-carbothioate

ID: ALA5208709

PubChem CID: 168297735

Max Phase: Preclinical

Molecular Formula: C15H9BrN2OS2

Molecular Weight: 377.29

Names and Identifiers

Canonical SMILES:  O=C(Sc1ncccn1)c1ccc(-c2ccc(Br)cc2)s1

Standard InChI:  InChI=1S/C15H9BrN2OS2/c16-11-4-2-10(3-5-11)12-6-7-13(20-12)14(19)21-15-17-8-1-9-18-15/h1-9H

Standard InChI Key:  CKAROBJLFOHZQI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    2.9349    0.0004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3109   -0.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4615   -1.3502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2425   -1.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664   -1.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7095   -0.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5365   -0.2677    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841    0.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0049    1.0755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6097    0.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0639    0.3406    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7192    0.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4452    1.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3765    1.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5058    0.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949   -0.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4815   -0.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0809    0.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8918    0.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1034    1.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8664   -0.1074    0.0000 Br  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  1  0
 11 12  1  0
 13 12  2  0
 10 14  2  0
 14 13  1  0
 15 12  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 15 20  1  0
 21 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5208709

   ---

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: 377.29

Molecular Weight (Monoisotopic): 375.9340

AlogP: 4.90

#Rotatable Bonds: 3

Polar Surface Area: 42.85

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.25

CX LogP: 5.19

CX LogD: 5.19

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.48

Np Likeness Score: -1.12

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