(2S,3S,4S,5R,6S)-6-[2-(benzyloxy)-5-carboxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 161574
• Molecular Formular: C20H20O10
• Molecular Mass: 420.3668
• Monoisotopic Mass: 420.10564684
• SMILES: c1(cc(c(cc1)OCc1ccccc1)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C(=O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@@H](O[C@H]([C@H]1O)C(=O)O)Oc1cc(ccc1OCc1ccccc1)C(=O)O
• InChI: InChI=1S/C20H20O10/c21-14-15(22)17(19(26)27)30-20(16(14)23)29-13-8-11(18(24)25)6-7-12(13)28-9-10-4-2-1-3-5-10/h1-8,14-17,20-23H,9H2,(H,24,25)(H,26,27)/t14-,15-,16+,17-,20+/m0/s1
• InChIKey: KIEDVJCLIRZVRU-SAGLZJIZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[2-(benzyloxy)-5-carboxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[2-(benzyloxy)-5-carboxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4-Benzyloxy-3-hydroxybenzoic Acid 3-O-β-D-Glucuronide

Database IDs

• PubChem SID: 162255709
• PubChem CID: 71313829

CALCULATED PROPERTIES

• Acid pKa: 2.7942371
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.072428
• LogD (pH = 7.4): -5.630324
• Log P: 0.9462717
• Molar Refractivity: 98.3827 cm^3
• Polarizability: 39.05855 Å^3
• Polar Surface Area: 162.98 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Light Yellow Solid

Safety Information

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

DETAILS

Toronto Research Chemicals - B279110

3,4-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide is 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)