3-[3-(4-chlorophenyl)-1-(5-chlorothiophen-2-yl)-3-hydroxypropyl]-4-hydroxy-2H-chromen-2-one

• ChemBase ID: 178660
• Molecular Formular: C22H16Cl2O4S
• Molecular Mass: 447.33104
• Monoisotopic Mass: 446.01463535
• SMILES: c1ccc2c(c1)c(c(c(=O)o2)C(CC(c1ccc(cc1)Cl)O)c1sc(cc1)Cl)O
• Canonical SMILES: Clc1ccc(cc1)C(CC(c1c(=O)oc2c(c1O)cccc2)c1ccc(s1)Cl)O
• InChI: InChI=1S/C22H16Cl2O4S/c23-13-7-5-12(6-8-13)16(25)11-15(18-9-10-19(24)29-18)20-21(26)14-3-1-2-4-17(14)28-22(20)27/h1-10,15-16,25-26H,11H2
• InChIKey: WRGOVNKNTPWHLZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[3-(4-chlorophenyl)-1-(5-chlorothiophen-2-yl)-3-hydroxypropyl]-4-hydroxy-2H-chromen-2-one
• IUPAC Traditional name: tioclomarol
• Synonyms: 3-[3-(4-Chlorophenyl)-1-(5-chloro-2-thienyl)-3-hydroxypropyl]-4-hydroxy-2H-1-benzopyran-2-one; Apegmone; 3-[5-Chloro-α-(p-chloro-β-hydroxyphenethyl)-2-thenyl]-4-hydroxy-coumarin; Tioclomarol

Database IDs

• CAS Number: 22619-35-8
• PubChem SID: 164234570
• PubChem CID: 54708299

CALCULATED PROPERTIES

• Acid pKa: 5.600212
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.1165543
• LogD (pH = 7.4): 3.602008
• Log P: 5.369852
• Molar Refractivity: 113.5915 cm^3
• Polarizability: 44.129524 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T444650

A coumarin (C755380) derivative classified as an anticoagulant.

REFERENCES

• Neau, J. et al.: Cereb. Dis., 11, 195 (2001)
• Boschetti, E. et al.: Chim. Ther., 7, 20 (2001)