5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-5-hydroxy-1,3-thiazolidine-2,4-dione

• ChemBase ID: 171135
• Molecular Formular: C19H20N2O4S
• Molecular Mass: 372.4381
• Monoisotopic Mass: 372.11437813
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC1(C(=O)NC(=O)S1)O)CC
• Canonical SMILES: CCc1ccc(nc1)CCOc1ccc(cc1)CC1(O)SC(=O)NC1=O
• InChI: InChI=1S/C19H20N2O4S/c1-2-13-3-6-15(20-12-13)9-10-25-16-7-4-14(5-8-16)11-19(24)17(22)21-18(23)26-19/h3-8,12,24H,2,9-11H2,1H3,(H,21,22,23)
• InChIKey: HDKWBDGQTUQSTO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-5-hydroxy-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: 5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-5-hydroxy-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-5-hydroxy-2,4-thiazolidinedione; 5-Hydroxy PioglitazoneDiscontinued

Database IDs

• CAS Number: 625853-74-9
• PubChem SID: 164227045
• PubChem CID: 46781869

CALCULATED PROPERTIES

• Acid pKa: 6.321241
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.8747604
• LogD (pH = 7.4): 2.1602306
• Log P: 2.9533536
• Molar Refractivity: 99.0436 cm^3
• Polarizability: 38.585155 Å^3
• Polar Surface Area: 88.52 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H952085

A novel metabolite of Pioglitazone (P471000).

REFERENCES

• Krieter, P., et al.: Drug Metab. Dispos., 22, 625 (1994)
• Tanis, S., et al.: J. Med. Chem., 39, 5053 (1994)
• Chilcott, J., et al.: Clin. Ther., 23, 1792 (1994)