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

• ChemBase ID: 161586
• Molecular Formular: C28H30O13
• Molecular Mass: 574.53
• Monoisotopic Mass: 574.16864102
• SMILES: c1(cc(c(cc1)OCc1ccccc1)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2cc(ccc2OCc2ccccc2)C(=O)OC)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C28H30O13/c1-15(29)37-22-23(38-16(2)30)25(39-17(3)31)28(41-24(22)27(33)35-5)40-21-13-19(26(32)34-4)11-12-20(21)36-14-18-9-7-6-8-10-18/h6-13,22-25,28H,14H2,1-5H3/t22-,23-,24-,25+,28+/m0/s1
• InChIKey: QWFJRTPAALCIAJ-XOJGLMOTSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162255721
• PubChem CID: 71313835

CALCULATED PROPERTIES

• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 2.761436
• LogD (pH = 7.4): 2.761436
• Log P: 2.761436
• Molar Refractivity: 135.3754 cm^3
• Polarizability: 54.745758 Å^3
• Polar Surface Area: 159.19 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Off-white Solid

DETAILS

Toronto Research Chemicals - B279120

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)