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

• ChemBase ID: 170127
• Molecular Formular: C22H22O12
• Molecular Mass: 478.40288
• Monoisotopic Mass: 478.11112614
• SMILES: c1c2c(ccc1O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C)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]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C22H22O12/c1-10(23)29-17-18(30-11(2)24)20(31-12(3)25)22(34-19(17)21(27)28-4)32-14-7-5-13-6-8-16(26)33-15(13)9-14/h5-9,17-20,22H,1-4H3/t17-,18-,19-,20+,22+/m1/s1
• InChIKey: GREJSCHGTQAQIT-YHZBMZHBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-[(2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-[(2-oxochromen-7-yl)oxy]oxane-2-carboxylate
• Synonyms: 2-Oxo-2H-1-benzopyran-7-yl-β-D-glucopyranosiduronic Acid Methyl Ester Triacetate; 7-Hydroxy Coumarin 2,3,4-Tri-O-acetyl-β-D-glucuronide Methyl Ester

Database IDs

• CAS Number: 168286-97-3
• PubChem SID: 164226037
• PubChem CID: 71748816

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 1.001271
• LogD (pH = 7.4): 1.001271
• Log P: 1.001271
• Molar Refractivity: 107.7649 cm^3
• Polarizability: 43.67143 Å^3
• Polar Surface Area: 149.96 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol

DETAILS

Toronto Research Chemicals - H924895

Coumarin derivative. Used in the preparation of Hydroxy Coumarin β-D-Glucuronide, a useful pharmacokinetic standard in metabolic studies.

REFERENCES

• Blankson, E., et al.: Biochem. Pharmacol., 42, 1241 (1991)
• Mead, J. et al.: Biochem. J. 61, 569 (1955)