5-({4-[2-(5-acetylpyridin-2-yl)(2H4)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

• ChemBase ID: 172090
• Molecular Formular: C19H18N2O4S
• Molecular Mass: 370.42222
• Monoisotopic Mass: 370.09872807
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)C(=O)C
• Canonical SMILES: O=C1NC(=O)C(S1)Cc1ccc(cc1)OCCc1ccc(cn1)C(=O)C
• InChI: InChI=1S/C19H18N2O4S/c1-12(22)14-4-5-15(20-11-14)8-9-25-16-6-2-13(3-7-16)10-17-18(23)21-19(24)26-17/h2-7,11,17H,8-10H2,1H3,(H,21,23,24)
• InChIKey: JMLKLMFMQRAJNI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-({4-[2-(5-acetylpyridin-2-yl)(^2H₄)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: 5-({4-[2-(5-acetylpyridin-2-yl)(^2H₄)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[4-[2-(5-Acetyl-2-pyridinyl)ethoxy-d4]phenyl]methyl]-2,4-thiazolidinedione; Keto-Pioglitazone (M-III)-d4; Keto Pioglitazone-d4 (M-III-d4)

Database IDs

• PubChem SID: 164228000
• PubChem CID: 45039630

CALCULATED PROPERTIES

• Acid pKa: 6.6146984
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.1270444
• LogD (pH = 7.4): 1.3495002
• Log P: 2.1725879
• Molar Refractivity: 98.1514 cm^3
• Polarizability: 38.169315 Å^3
• Polar Surface Area: 85.36 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethanol; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 118-120°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - K200602

A labelled metabolite of Pioglitazone (P471000).

REFERENCES

• Tanis, S.P., et al.: J. Med. Chem., 39, 5053 (1996)