methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-5-(methoxycarbonyl)phenoxy]oxane-2-carboxylate

• ChemBase ID: 167780
• Molecular Formular: C15H18O10
• Molecular Mass: 358.29742
• Monoisotopic Mass: 358.08999678
• SMILES: c1c(c(cc(c1)C(=O)OC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)OC)O
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2cc(ccc2O)C(=O)OC)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H18O10/c1-22-13(20)6-3-4-7(16)8(5-6)24-15-11(19)9(17)10(18)12(25-15)14(21)23-2/h3-5,9-12,15-19H,1-2H3/t9-,10-,11+,12-,15+/m0/s1
• InChIKey: LEDWYOZSSVUTIR-QKZHPOIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-5-(methoxycarbonyl)phenoxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-5-(methoxycarbonyl)phenoxy]oxane-2-carboxylate
• Synonyms: 5-Carboxy-2-hydroxyphenyl β-D-Glucopyranosiduronic Acid Dimethyl Diester; 3,4-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide Dimethyl Diester

Database IDs

• PubChem SID: 162261913
• PubChem CID: 71316229

CALCULATED PROPERTIES

• Acid pKa: 8.846826
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.4325012
• LogD (pH = 7.4): -0.44743773
• Log P: -0.43230736
• Molar Refractivity: 78.826 cm^3
• Polarizability: 31.851215 Å^3
• Polar Surface Area: 151.98 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Off-white Solid

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D451770

Protected 3,4-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide (D451685). A metabolite of Protocatechuic aldehyde, a major bioactive phenolic acid in the roots of Salvia miltiorrhiza.

REFERENCES

• Rao, S., et al.: J. Biotechnol., 76, 137 (2000)
• Zhang, Y., et al.: Drug Metab. Dispos., 32, 752 (2000)
• Pan, J., et al.: J. Pharm. Biomed. Anal., 42, 565 (2000)