3-{3,5-dimethyl-4-[3-(3-methyl-1,2-oxazol-5-yl)propoxy]phenyl}-5-(trifluoromethyl)-1,2,4-oxadiazole

• ChemBase ID: 6319
• Molecular Formular: C18H18F3N3O3
• Molecular Mass: 381.3490296
• Monoisotopic Mass: 381.13002611
• SMILES: o1nc(C)cc1CCCOc1c(C)cc(cc1C)c1noc(n1)C(F)(F)F
• Canonical SMILES: Cc1noc(c1)CCCOc1c(C)cc(cc1C)c1noc(n1)C(F)(F)F
• InChI: InChI=1S/C18H18F3N3O3/c1-10-7-13(16-22-17(27-24-16)18(19,20)21)8-11(2)15(10)25-6-4-5-14-9-12(3)23-26-14/h7-9H,4-6H2,1-3H3
• InChIKey: KQOXLKOJHVFTRN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{3,5-dimethyl-4-[3-(3-methyl-1,2-oxazol-5-yl)propoxy]phenyl}-5-(trifluoromethyl)-1,2,4-oxadiazole
• IUPAC Traditional name: pleconaril
• Synonyms: 3-{3,5-DIMETHYL-4-[3-(3-METHYL-ISOXAZOL-5-YL)-PROPOXY]-PHENYL}-5-TRIFLUOROMETHYL-[1,2,4]OXADIAZOLE; 3-[3,5-Dimethyl-4-[3-(3-methyl-5-isoxazolyl)propoxy]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole; Picovir; VP 63843; Win 63843; Pleconaril

Database IDs

• CAS Number: 153168-05-9
• PubChem SID: 162103418
• PubChem CID: 1684

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 5.0391607
• LogD (pH = 7.4): 5.03922
• Log P: 5.0392203
• Molar Refractivity: 104.1153 cm^3
• Polarizability: 33.92289 Å^3
• Polar Surface Area: 74.18 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.7
• LOG S: -4.24
• Solubility (Water): 2.19e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 58-60°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

DrugBank - DB08716

Drug information: experimental

Toronto Research Chemicals - P580350

Picornavirus replication inhibitor. Antiviral.

REFERENCES

• Kearns, G.L., J. Clin. Pharmacol., 39, 613 (1999)
• Schmidtke, M. et al.: Antiviral Res. 81, 56 (2009)