S-(Pyrimidin-2-yl)-5-phenylfuran-2-carbothioate

ID: ALA5177782

PubChem CID: 168275028

Max Phase: Preclinical

Molecular Formula: C15H10N2O2S

Molecular Weight: 282.32

Names and Identifiers

Canonical SMILES:  O=C(Sc1ncccn1)c1ccc(-c2ccccc2)o1

Standard InChI:  InChI=1S/C15H10N2O2S/c18-14(20-15-16-9-4-10-17-15)13-8-7-12(19-13)11-5-2-1-3-6-11/h1-10H

Standard InChI Key:  YBLPIBQVEVGXEC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    2.5350    0.0229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190   -0.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815   -1.3346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8662   -1.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823   -1.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135   -0.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406   -0.2657    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9766    0.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5894    1.0843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1982    0.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686    0.3193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1311    0.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8685    1.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0465    1.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9143    0.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0916   -0.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8747   -0.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4823    0.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3050    0.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5201    1.1245    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  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
M  END

Alternative Forms

1. Parent:

   

   ALA5177782

   ---

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: 282.32

Molecular Weight (Monoisotopic): 282.0463

AlogP: 3.67

#Rotatable Bonds: 3

Polar Surface Area: 55.99

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.20

CX LogP: 3.49

CX LogD: 3.49

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.54

Np Likeness Score: -1.10

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