TILOMISOLE

ID: ALA2104737

Cas Number: 58433-11-7

PubChem CID: 42747

Max Phase: Phase

Molecular Formula: C17H11ClN2O2S

Molecular Weight: 342.81

Molecule Type: Small molecule

Names and Identifiers

Synonyms: WY-18,251 | WY-18251 | TILOMISOLE|58433-11-7|Wy-18251|2-[1-(4-chlorophenyl)-[1,3]thiazolo[3,2-a]benzimidazol-2-yl]acetic acid|WY-18,251|Wy 18251|Tilomisol|3-(p-Chlorophenyl)thiazolo(3,2-a)benzimidazole-2-acetic acid|651G60U372|Tilomisolum|Thiazolo(3,2-a)benzimidazole-2-acetic acid, 3-(4-chlorophenyl)|Tilomisol [Spanish]|Tilomisolum [Latin]|Tilomisole [USAN:INN]|UNII-651G60U372|TILOMISOLE [INN]|Tilomisole (USAN/INN)|TILOMISOLE [USAN]|2-[1-(4-chlorophenyl)-[1,3]thiazolo[3,2-a]benzo[d]imidazol-2-ylShow More⌵

Canonical SMILES:  O=C(O)Cc1sc2nc3ccccc3n2c1-c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C17H11ClN2O2S/c18-11-7-5-10(6-8-11)16-14(9-15(21)22)23-17-19-12-3-1-2-4-13(12)20(16)17/h1-8H,9H2,(H,21,22)

Standard InChI Key:  PUYFLGQZLHVTHX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -1.2875    2.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875    1.0833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667    2.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    2.3583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4167    1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2875    3.1083    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9833    1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292    2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292    0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000    2.5708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000    0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792    0.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -2.9792    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0875   -0.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2083    0.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2750   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458   -0.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  1  2  0
  5  2  1  0
  6  1  1  0
  7  2  1  0
  8  4  1  0
  9  3  1  0
 10  9  1  0
 11  5  1  0
 12 10  2  0
 13 11  2  0
 14 11  1  0
 15 17  1  0
 16 10  1  0
 17 14  2  0
 18 13  1  0
 19 15  1  0
 20  7  1  0
 21  8  1  0
 22 20  2  0
 23 21  2  0
  7  8  2  0
  5  3  2  0
 22 23  1  0
 18 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2104737

   TILOMISOLE

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 342.81

Molecular Weight (Monoisotopic): 342.0230

AlogP: 4.50

#Rotatable Bonds: 3

Polar Surface Area: 54.60

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.81

CX Basic pKa: 3.86

CX LogP: 3.74

CX LogD: 1.48

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.60

Np Likeness Score: -1.34

References

1. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

2. Bell SC, Wei PH..  (1976)  Syntheses of heterocylic fused thiazole acetic acids. 2.,  19  (4): [PMID:1263204] [10.1021/jm00226a016]

3. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(3):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names
• IMI-CARE SARS-CoV-2 Data