5-({4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

• ChemBase ID: 171134
• Molecular Formular: C19H20N2O4S
• Molecular Mass: 372.4381
• Monoisotopic Mass: 372.11437813
• SMILES: n1cc(ccc1C(COc1ccc(cc1)CC1C(=O)NC(=O)S1)O)CC
• Canonical SMILES: CCc1ccc(nc1)C(COc1ccc(cc1)CC1SC(=O)NC1=O)O
• InChI: InChI=1S/C19H20N2O4S/c1-2-12-5-8-15(20-10-12)16(22)11-25-14-6-3-13(4-7-14)9-17-18(23)21-19(24)26-17/h3-8,10,16-17,22H,2,9,11H2,1H3,(H,21,23,24)
• InChIKey: RMTFRGFLVHAYCI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-({4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: 5-({4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[4-[2-(5-Ethyl-2-pyridinyl]-2-hydroxyethoxy]phenyl]methyl]-2,4-thiazolidinedione; Hydroxy Pioglitazone (M-II) (Mixture of Diastereomers)

Database IDs

• CAS Number: 101931-00-4
• PubChem SID: 164227044
• PubChem CID: 9864268

CALCULATED PROPERTIES

• Acid pKa: 6.623887
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.7128499
• LogD (pH = 7.4): 2.0332177
• Log P: 2.7250235
• Molar Refractivity: 98.729 cm^3
• Polarizability: 38.65045 Å^3
• Polar Surface Area: 88.52 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO
• Apperance: White to Off-White Solid
• Melting Point: 128-130°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H952080

A metabolite of Pioglitazone (P471000).

REFERENCES

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