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

• ChemBase ID: 171132
• Molecular Formular: C19H20N2O4S
• Molecular Mass: 372.4381
• Monoisotopic Mass: 372.11437813
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)C(C)O
• Canonical SMILES: O=C1NC(=O)C(S1)Cc1ccc(cc1)OCCc1ccc(cn1)C(O)C
• InChI: InChI=1S/C19H20N2O4S/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/h2-7,11-12,17,22H,8-10H2,1H3,(H,21,23,24)
• InChIKey: OXVFDZYQLGRLCD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(4-{2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: 5-[(4-{2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[4-[2-[5-(1-Hydroxyethyl)-2-pyridinyl]ethoxy]phenyl]methyl]-2,4-thiazolidinedione; Hydroxy Pioglitazone (M-IV)

Database IDs

• CAS Number: 146062-44-4
• PubChem SID: 164227042
• PubChem CID: 4147757

CALCULATED PROPERTIES

• Acid pKa: 6.6207876
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.150306
• LogD (pH = 7.4): 1.4401096
• Log P: 2.1429474
• Molar Refractivity: 98.9833 cm^3
• Polarizability: 38.6488 Å^3
• Polar Surface Area: 88.52 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: 148-150°C

Safety Information

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

DETAILS

Toronto Research Chemicals - H952075

A metabolite of Pioglitazone (P471000).

REFERENCES

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