(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3-methyl-4-oxo-2-phenyl-4H-chromene-8-carbonyloxy)oxane-2-carboxylic acid

• ChemBase ID: 173727
• Molecular Formular: C23H20O10
• Molecular Mass: 456.3989
• Monoisotopic Mass: 456.10564684
• SMILES: c1(cccc2c1oc(c(c2=O)C)c1ccccc1)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC(=O)c2cccc3c2oc(c2ccccc2)c(c3=O)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C23H20O10/c1-10-14(24)12-8-5-9-13(19(12)31-18(10)11-6-3-2-4-7-11)22(30)33-23-17(27)15(25)16(26)20(32-23)21(28)29/h2-9,15-17,20,23,25-27H,1H3,(H,28,29)/t15-,16-,17+,20-,23-/m0/s1
• InChIKey: QTFLEEJQZRBOAR-ZFMFMYKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3-methyl-4-oxo-2-phenyl-4H-chromene-8-carbonyloxy)oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3-methyl-4-oxo-2-phenylchromene-8-carbonyloxy)oxane-2-carboxylic acid
• Synonyms: 1-(3-Methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylate) β-D-Glucopyranuronic Acid; 3-Methylflavone-8-carboxylic Acid Acyl-β-D-glucuronide

Database IDs

• CAS Number: 60218-13-5
• PubChem SID: 164229637
• PubChem CID: 71750357

CALCULATED PROPERTIES

• Acid pKa: 2.7341704
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -1.424799
• LogD (pH = 7.4): -2.2261376
• Log P: 1.272725
• Molar Refractivity: 110.8831 cm^3
• Polarizability: 43.25821 Å^3
• Polar Surface Area: 159.82 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M305225

A metabolite of Flavoxate hydrochloride (FX) in human.

REFERENCES

• Da Re, P., et al.: J. Med. Chem., 2, 263 (1960)
• Bertoli, M., et al.: Pharmacol. Res. Commun., 8, 417 (1960)
• Ammon, S., et al.: Br. J. Clin. Pharma., 48, 317 (1960)