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

• ChemBase ID: 167777
• Molecular Formular: C21H24O13
• Molecular Mass: 484.40746
• Monoisotopic Mass: 484.12169083
• SMILES: c1(cc(cc(c1)C(=O)OC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)O
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2cc(O)cc(c2)C(=O)OC)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C21H24O13/c1-9(22)30-15-16(31-10(2)23)18(32-11(3)24)21(34-17(15)20(27)29-5)33-14-7-12(19(26)28-4)6-13(25)8-14/h6-8,15-18,21,25H,1-5H3/t15-,16-,17-,18+,21+/m0/s1
• InChIKey: CCZIKCXUEYMAFV-ARWBCWGVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[3-hydroxy-5-(methoxycarbonyl)phenoxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[3-hydroxy-5-(methoxycarbonyl)phenoxy]oxane-2-carboxylate
• Synonyms: α-Resorcylic Acid 3-O-β-D-Glucuronide Triacetyl Dimethyl Diester; 5-Carboxyresorcinol 3-O-β-D-Glucuronide Triacetyl Dimethyl Diester; 3,5-Dihydroxybenzoic Acid 3-O-(2,3,4-Tri-O-acetyl-β-D-glucuronide) Dimethyl Diester

Database IDs

• PubChem SID: 162261910
• PubChem CID: 71316227

CALCULATED PROPERTIES

• Acid pKa: 9.043551
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 0.89094555
• LogD (pH = 7.4): 0.88138133
• Log P: 0.8910689
• Molar Refractivity: 106.2805 cm^3
• Polarizability: 43.419804 Å^3
• Polar Surface Area: 170.19 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Off-white Solid

DETAILS

Toronto Research Chemicals - D451730

Protected 3,5-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide (D451705). A possible glucuronide metabolite of alkylresorcinol in humans.