methyl (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[(2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylate

• ChemBase ID: 170396
• Molecular Formular: C16H16O9
• Molecular Mass: 352.29284
• Monoisotopic Mass: 352.07943209
• SMILES: c1c2c(ccc1O[C@H]1O[C@@H]([C@H](O)[C@@H](O)[C@H]1O)C(=O)OC)ccc(=O)o2
• Canonical SMILES: COC(=O)[C@H]1O[C@H](Oc2ccc3c(c2)oc(=O)cc3)[C@@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C16H16O9/c1-22-15(21)14-12(19)11(18)13(20)16(25-14)23-8-4-2-7-3-5-10(17)24-9(7)6-8/h2-6,11-14,16,18-20H,1H3/t11-,12-,13+,14-,16+/m1/s1
• InChIKey: NLCKRAQRRCQKMC-SSZWKKLZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[(2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[(2-oxochromen-7-yl)oxy]oxane-2-carboxylate
• Synonyms: 2-Oxo-2H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid Methyl Ester; Umbelliferyl β-D-Glucuronide Methyl Ester; 7-Hydroxy Coumarin β-D-Glucuronide Methyl Ester

Database IDs

• CAS Number: 1176514-11-6
• PubChem SID: 164226306
• PubChem CID: 71748956

CALCULATED PROPERTIES

• Acid pKa: 12.165701
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.3221053
• LogD (pH = 7.4): -0.32211265
• Log P: -0.3221052
• Molar Refractivity: 80.3104 cm^3
• Polarizability: 32.099537 Å^3
• Polar Surface Area: 131.75 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol

DETAILS

Toronto Research Chemicals - H924885

Coumarin derivative. A metabolite of Coumarin. Useful as a pharmacokinetic standard in metabolic studies.

REFERENCES

• Blankson, E., et al.: Biochem. Pharmacol., 42, 1241 (1991)
• Steensma, A., et al.: Xenobiotica, 24, 893 (1991)
• Fisher, R., et al.: Toxicol. Methods, 5, 99 (1991)
• Ekins, S., et al.: Drug Metab. Dispos., 24, 990 (1996)