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

• ChemBase ID: 166162
• Molecular Formular: C18H16N2O5S
• Molecular Mass: 372.39504
• Monoisotopic Mass: 372.07799262
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)C(=O)O
• Canonical SMILES: O=C1NC(=O)C(S1)Cc1ccc(cc1)OCCc1ccc(cn1)C(=O)O
• InChI: InChI=1S/C18H16N2O5S/c21-16-15(26-18(24)20-16)9-11-1-5-14(6-2-11)25-8-7-13-4-3-12(10-19-13)17(22)23/h1-6,10,15H,7-9H2,(H,22,23)(H,20,21,24)
• InChIKey: SLOBZACXYXBLIT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)pyridine-3-carboxylic acid
• IUPAC Traditional name: 6-(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)pyridine-3-carboxylic acid
• Synonyms: 6-[2-[4-[(2,4-Dioxo-5-thiazolidinyl)methyl]phenoxy]ethyl]-3-pyridinecarboxylic Acid; 5-Desethyl 5-Carboxy Pioglitazone

Database IDs

• CAS Number: 186751-40-6
• PubChem SID: 162260295
• PubChem CID: 45038858

CALCULATED PROPERTIES

• Acid pKa: 1.9513911
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.51592845
• LogD (pH = 7.4): -1.7248821
• Log P: 0.9402652
• Molar Refractivity: 95.0048 cm^3
• Polarizability: 36.7299 Å^3
• Polar Surface Area: 105.59 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White to Light Yellow Solid
• Melting Point: 109-114°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D288870

A metabolite of Pioglitazone (P471000). Antidiabetic.

REFERENCES

• Krieter, P., et al.: Drug Metab. Dispos., 22, 625 (1994)
• Tanis, S., et al.: J. Med. Chem., 39, 5053 (1994)
• Chilcott, J., et al.: Clin. Ther., 23, 1792 (1994)