sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-oxo(2H5)-2H-chromen-7-yl]oxy}oxane-2-carboxylate

• ChemBase ID: 170394
• Molecular Formular: C15H13NaO9
• Molecular Mass: 360.24809
• Monoisotopic Mass: 360.04572628
• SMILES: c1c2c(ccc1O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)[O-])ccc(=O)o2.[Na+]
• Canonical SMILES: [O-]C(=O)[C@@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3)[C@H]([C@H]([C@@H]1O)O)O.[Na+]
• InChI: InChI=1S/C15H14O9.Na/c16-9-4-2-6-1-3-7(5-8(6)23-9)22-15-12(19)10(17)11(18)13(24-15)14(20)21;/h1-5,10-13,15,17-19H,(H,20,21);/q;+1/p-1/t10-,11-,12+,13-,15+;/m0./s1
• InChIKey: SKHLGBDGEPDEME-KSOKONAESA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-oxo(^2H₅)-2H-chromen-7-yl]oxy}oxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-oxo(^2H₅)chromen-7-yl]oxy}oxane-2-carboxylate
• Synonyms: 2-Oxo-2H-1-benzopyran-7-yl-d7 β-D-Glucopyranosiduronic Acid Monosodium Salt; Umbelliferyl-d7 β-D-Glucuronide Sodium Salt; 7-Hydroxy Coumarin-d5 β-D-Glucuronide Sodium Salt

Database IDs

• PubChem SID: 164226304
• PubChem CID: 49849367

CALCULATED PROPERTIES

• Acid pKa: 2.979382
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.9493296
• LogD (pH = 7.4): -3.9449944
• Log P: -0.46799925
• Molar Refractivity: 86.3784 cm^3
• Polarizability: 29.958012 Å^3
• Polar Surface Area: 145.58 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H924882

A labelled metabolite of 7-Ethoxycoumarin and 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)