(5Z)-5-[(4-{2-[5-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl]ethoxy}phenyl)methylidene]-1,3-thiazolidine-2,4-dione

• ChemBase ID: 173593
• Molecular Formular: C21H20N2O5S
• Molecular Mass: 412.4589
• Monoisotopic Mass: 412.10929275
• SMILES: n1cc(ccc1CCOc1ccc(cc1)/C=C\1/C(=O)NC(=O)S1)C1(OCCO1)C
• Canonical SMILES: O=C1NC(=O)/C(=C/c2ccc(cc2)OCCc2ccc(cn2)C2(C)OCCO2)/S1
• InChI: InChI=1S/C21H20N2O5S/c1-21(27-10-11-28-21)15-4-5-16(22-13-15)8-9-26-17-6-2-14(3-7-17)12-18-19(24)23-20(25)29-18/h2-7,12-13H,8-11H2,1H3,(H,23,24,25)/b18-12-
• InChIKey: DLZDCEKRRJKXND-PDGQHHTCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-5-[(4-{2-[5-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl]ethoxy}phenyl)methylidene]-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: (5Z)-5-[(4-{2-[5-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl]ethoxy}phenyl)methylidene]-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[4-[2-[5-(2-Methyl-1,3-dioxolan-2-yl)-2-pyridinyl]ethoxy]phenyl]methylene]-2,4-thiazolidinedione; 5-[4-[2-[5-(2-Methyl-1,3-dioxolan-2-yl)-2-pyridyl]ethoxy]benzylidene]-2,4-thiazolidinedione

Database IDs

• CAS Number: 184766-62-9
• PubChem SID: 164229503
• PubChem CID: 6140078

CALCULATED PROPERTIES

• Acid pKa: 7.90286
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.6990047
• LogD (pH = 7.4): 2.6310058
• Log P: 2.74879
• Molar Refractivity: 109.7181 cm^3
• Polarizability: 42.209705 Å^3
• Polar Surface Area: 86.75 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 163-164°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M303675

A metabolite of Pioglitazone (P471000).

REFERENCES

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