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

• ChemBase ID: 171292
• Molecular Formular: C18H19N3O4S
• Molecular Mass: 373.42616
• Monoisotopic Mass: 373.1096271
• SMILES: c1cc(cnc1N(CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)C)O
• Canonical SMILES: O=C1NC(=O)C(S1)Cc1ccc(cc1)OCCN(c1ccc(cn1)O)C
• InChI: InChI=1S/C18H19N3O4S/c1-21(16-7-4-13(22)11-19-16)8-9-25-14-5-2-12(3-6-14)10-15-17(23)20-18(24)26-15/h2-7,11,15,22H,8-10H2,1H3,(H,20,23,24)
• InChIKey: AGQGGZNSVNKGDU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(4-{2-[(5-hydroxypyridin-2-yl)(methyl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: 5-[(4-{2-[(5-hydroxypyridin-2-yl)(methyl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[4-[2-[(5-Hydroxy-2-pyridinyl)methylamino]ethoxy]phenyl]methyl]-2,4-thiazolidinedione; 5-Hydroxy Rosiglitazone

Database IDs

• CAS Number: 257883-22-0
• PubChem SID: 164227202
• PubChem CID: 9864316

CALCULATED PROPERTIES

• Acid pKa: 6.7648478
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.0033488
• LogD (pH = 7.4): 1.9210311
• Log P: 2.26895
• Molar Refractivity: 99.7708 cm^3
• Polarizability: 38.033707 Å^3
• Polar Surface Area: 91.76 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 72-74°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H953440

A metabolite of Rosiglitazone.

REFERENCES

• Balton, G.C., et al.: Xenobiotica, 26, 6, 627 (1996)