5-[(4-hydroxyphenyl)methyl]-1,3-thiazolidine-2,4-dione

• ChemBase ID: 170282
• Molecular Formular: C10H9NO3S
• Molecular Mass: 223.24836
• Monoisotopic Mass: 223.03031415
• SMILES: Oc1ccc(cc1)CC1C(=O)NC(=O)S1
• Canonical SMILES: O=C1NC(=O)SC1Cc1ccc(cc1)O
• InChI: InChI=1S/C10H9NO3S/c12-7-3-1-6(2-4-7)5-8-9(13)11-10(14)15-8/h1-4,8,12H,5H2,(H,11,13,14)
• InChIKey: NKOHRVBBQISBSB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(4-hydroxyphenyl)methyl]-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: 5-[(4-hydroxyphenyl)methyl]-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[(4-Hydroxyphenyl)methyl]-2,4-thiazolidinedione; U 90441; 5-(4-Hydroxybenzyl)thiazolidine-2,4-dione

Database IDs

• CAS Number: 74772-78-4
• PubChem SID: 164226192
• PubChem CID: 10198397

CALCULATED PROPERTIES

• Acid pKa: 6.613028
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.6118892
• LogD (pH = 7.4): 0.81747115
• Log P: 1.643761
• Molar Refractivity: 56.6334 cm^3
• Polarizability: 21.998741 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO
• Apperance: Off-White Solid
• Melting Point: 145-147°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H829980

A metabolite of Pioglitazone (P471000) in humans.

REFERENCES

• Zhong, W. Z., et al.: J. Pharma. Biomed. Anal., 14, 465 (1996)
• Kiyota, Y., et al.: Arzneim.-Forsch., 47, 22 (1996)