methyl (2S,3S,4S,5R,6S)-6-[2-(benzyloxy)-5-(methoxycarbonyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 161585
• Molecular Formular: C22H24O10
• Molecular Mass: 448.41996
• Monoisotopic Mass: 448.13694697
• SMILES: c1(cc(c(cc1)OCc1ccccc1)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)OC)C(=O)OC
• Canonical SMILES: COC(=O)c1ccc(c(c1)O[C@@H]1O[C@@H](C(=O)OC)[C@H]([C@@H]([C@@H]1O)O)O)OCc1ccccc1
• InChI: InChI=1S/C22H24O10/c1-28-20(26)13-8-9-14(30-11-12-6-4-3-5-7-12)15(10-13)31-22-18(25)16(23)17(24)19(32-22)21(27)29-2/h3-10,16-19,22-25H,11H2,1-2H3/t16-,17-,18+,19-,22+/m0/s1
• InChIKey: ZJSHSCULHYLTPE-KSSXRGRSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-6-[2-(benzyloxy)-5-(methoxycarbonyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-6-[2-(benzyloxy)-5-(methoxycarbonyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: 4-Benzyloxy-3-hydroxybenzoic Acid 3-O-β-D-Glucuronide Dimethyl Diester

Database IDs

• PubChem SID: 162255720
• PubChem CID: 71313834

CALCULATED PROPERTIES

• Acid pKa: 12.165585
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.4380597
• LogD (pH = 7.4): 1.4380524
• Log P: 1.4380598
• Molar Refractivity: 107.9209 cm^3
• Polarizability: 43.177998 Å^3
• Polar Surface Area: 140.98 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Light Yellow Powder

Safety Information

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

DETAILS

Toronto Research Chemicals - B279115

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)