2-(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}(2H4)ethyl)-5-ethylpyridin-1-ium-1-olate

• ChemBase ID: 176744
• Molecular Formular: C19H20N2O4S
• Molecular Mass: 372.4381
• Monoisotopic Mass: 372.11437813
• SMILES: [n+]1(cc(ccc1CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)CC)[O-]
• Canonical SMILES: CCc1ccc([n+](c1)[O-])CCOc1ccc(cc1)CC1SC(=O)NC1=O
• InChI: InChI=1S/C19H20N2O4S/c1-2-13-3-6-15(21(24)12-13)9-10-25-16-7-4-14(5-8-16)11-17-18(22)20-19(23)26-17/h3-8,12,17H,2,9-11H2,1H3,(H,20,22,23)
• InChIKey: YTKQAGFCVMHNHM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}(^2H₄)ethyl)-5-ethylpyridin-1-ium-1-olate
• IUPAC Traditional name: 2-(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}(^2H₄)ethyl)-5-ethylpyridin-1-ium-1-olate
• Synonyms: 5-[[4-[2-(5-Ethyl-2-pyridinyl]ethoxy-d4]phenyl]methyl]-2,4-thiazolidinedione N-Oxide; Pioglitazone-d4 N-Oxide

Database IDs

• PubChem SID: 164232654
• PubChem CID: 71751674

CALCULATED PROPERTIES

• Acid pKa: 6.6135893
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.4599717
• LogD (pH = 7.4): 1.6689241
• Log P: 2.4918368
• Molar Refractivity: 101.6145 cm^3
• Polarizability: 38.499783 Å^3
• Polar Surface Area: 80.86 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P471012

A labelled metabolite of Pioglitazone (P471000).

REFERENCES

• Tanis, S.P., et al.: J. Med. Chem., 39, 5053 (1999)