(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-oxo(4a,5,6,7,8,8a-13C6)-2H-chromen-7-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 170395
• Molecular Formular: C15H14O9
• Molecular Mass: 344.22218903
• Monoisotopic Mass: 344.08391106
• SMILES: [13cH]1[13c]2[13c]([13cH][13cH][13c]1O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)ccc(=O)o2
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](O[13c]2[13cH][13cH][13c]3[13c]([13cH]2)oc(=O)cc3)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H14O9/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)/t10-,11-,12+,13-,15+/m0/s1/i1+1,3+1,5+1,6+1,7+1,8+1
• InChIKey: PRYLPCLGPXGILY-LRJGBYDFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-oxo(4a,5,6,7,8,8a-^1^3C₆)-2H-chromen-7-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-oxo(4a,5,6,7,8,8a-^1^3C₆)chromen-7-yl]oxy}oxane-2-carboxylic acid
• Synonyms: 2-Oxo-2H-1-benzopyran-7-yl-13C6 β-D-Glucopyranosiduronic Acid; Umbelliferyl-13C6 β-D-Glucuronide; 7-Hydroxy Coumarin-13C6 β-D-Glucuronide

Database IDs

• PubChem SID: 164226305
• PubChem CID: 71748955

CALCULATED PROPERTIES

• Acid pKa: 2.979382
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.9493296
• LogD (pH = 7.4): -3.9449944
• Log P: -0.46799925
• Molar Refractivity: 75.5413 cm^3
• Polarizability: 30.05365 Å^3
• Polar Surface Area: 142.75 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H924883

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)