{6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxidanesulfonic acid

• ChemBase ID: 171295
• Molecular Formular: C18H19N3O7S2
• Molecular Mass: 453.48936
• Monoisotopic Mass: 453.06644196
• SMILES: c1cc(cnc1N(CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)C)OS(=O)(=O)O
• Canonical SMILES: O=C1NC(=O)C(S1)Cc1ccc(cc1)OCCN(c1ccc(cn1)OS(=O)(=O)O)C
• InChI: InChI=1S/C18H19N3O7S2/c1-21(16-7-6-14(11-19-16)28-30(24,25)26)8-9-27-13-4-2-12(3-5-13)10-15-17(22)20-18(23)29-15/h2-7,11,15H,8-10H2,1H3,(H,20,22,23)(H,24,25,26)
• InChIKey: WAGUBJKZLRLKGR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxidanesulfonic acid
• IUPAC Traditional name: {6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxidanesulfonic acid
• Synonyms: 5-[[4-[2-[Methyl[5-(sulfooxy)-2-pyridinyl]amino]ethoxy]phenyl]methyl]-2,4-thiazolidinedione; 5-Hydroxy Rosiglitazone Sulfate

Database IDs

• CAS Number: 288853-63-4
• PubChem SID: 164227205
• PubChem CID: 9846723

CALCULATED PROPERTIES

• Acid pKa: -2.541724
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -0.14827187
• LogD (pH = 7.4): -0.9025262
• Log P: -0.36772674
• Molar Refractivity: 109.7626 cm^3
• Polarizability: 42.85662 Å^3
• Polar Surface Area: 135.13 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Yellow Solid

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - H953450

A metabolite of Rosiglitazone.

REFERENCES

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