(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetyl}oxy)oxane-2-carboxylic acid

• ChemBase ID: 178707
• Molecular Formular: C21H23NO9
• Molecular Mass: 433.40862
• Monoisotopic Mass: 433.13728132
• SMILES: c1cc(n(c1C(=O)c1ccc(cc1)C)C)CC(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: O=C(Cc1ccc(n1C)C(=O)c1ccc(cc1)C)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H23NO9/c1-10-3-5-11(6-4-10)15(24)13-8-7-12(22(13)2)9-14(23)30-21-18(27)16(25)17(26)19(31-21)20(28)29/h3-8,16-19,21,25-27H,9H2,1-2H3,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1
• InChIKey: MEFIGCPEYJZFFC-ZFORQUDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetyl}oxy)oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl}oxy)oxane-2-carboxylic acid
• Synonyms: 1-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate]β-D-Glucopyranuronic Acid; Tolmetin Glucuronide; Tolmetin β-D-Glucuronide

Database IDs

• CAS Number: 71595-19-2
• PubChem SID: 164234617
• PubChem CID: 155656

CALCULATED PROPERTIES

• Acid pKa: 3.1217868
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.5708667
• LogD (pH = 7.4): -2.6786883
• Log P: 0.7795374
• Molar Refractivity: 104.6914 cm^3
• Polarizability: 41.235687 Å^3
• Polar Surface Area: 155.52 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Beige Solid
• Melting Point: 139-142°C

Safety Information

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

DETAILS

Toronto Research Chemicals - T535360

A metabolite of Tolmetin.

REFERENCES

• Smith, P., et al.: J. Clin. Invest., 77, 934 (1986)
• Hyneck, M., et al.: Clin. Pharmacol. Ther., 44, 107 (1986)
• Ojingwa, J., et al.: Xenobiotica, 24, 495 (1986)
• Ebner, T., et al.: Drug Metab. Dispos., 27, 1143 (1986)