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

• ChemBase ID: 163782
• Molecular Formular: C19H18N2O5S
• Molecular Mass: 386.42162
• Monoisotopic Mass: 386.09364269
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC1C(=O)NC(=O)S1)CC(=O)O
• Canonical SMILES: OC(=O)Cc1ccc(nc1)CCOc1ccc(cc1)CC1SC(=O)NC1=O
• InChI: InChI=1S/C19H18N2O5S/c22-17(23)10-13-1-4-14(20-11-13)7-8-26-15-5-2-12(3-6-15)9-16-18(24)21-19(25)27-16/h1-6,11,16H,7-10H2,(H,22,23)(H,21,24,25)
• InChIKey: OIQJTMMAMWFMQR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[6-(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)pyridin-3-yl]acetic acid
• IUPAC Traditional name: [6-(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)pyridin-3-yl]acetic acid
• Synonyms: 6-[2-[4-[(2,4-Dioxo-5-thiazolidinyl)methyl]phenoxy]ethyl]-3-pyridineacetic Acid; 5-[[4-[2-[5-(1-Carboxymethyl)-2-pyridinyl]ethoxy]phenyl]methyl]-2,4-thiazolidinedione; Pioglitazone Metabolite M5; Carboxy Pioglitazone (M-V)

Database IDs

• CAS Number: 146062-48-8
• PubChem SID: 162257917
• PubChem CID: 10068721

CALCULATED PROPERTIES

• Acid pKa: 3.6055548
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.46649307
• LogD (pH = 7.4): -1.7934842
• Log P: 0.9550633
• Molar Refractivity: 99.0562 cm^3
• Polarizability: 38.583096 Å^3
• Polar Surface Area: 105.59 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C179040

A metabolite of the antidiabetic Pioglitazone (P471000).

REFERENCES

• Maeshiba, Y. et al.: Arzneim-Forsch., 47, 29 (1997)
• Zhong, W.Z. et al.: J. Pharmac. Biomed, Anal., 14, 465 (1997)
• Shen, Z. et al.: Xenobiotica, 33, 499 (1997)