(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(methoxycarbonyl)benzoyloxy]oxane-2-carboxylic acid

• ChemBase ID: 174444
• Molecular Formular: C15H16O10
• Molecular Mass: 356.28154
• Monoisotopic Mass: 356.07434671
• SMILES: c1ccc(c(c1)C(=O)OC)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: COC(=O)c1ccccc1C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H16O10/c1-23-13(21)6-4-2-3-5-7(6)14(22)25-15-10(18)8(16)9(17)11(24-15)12(19)20/h2-5,8-11,15-18H,1H3,(H,19,20)/t8-,9-,10+,11-,15-/m0/s1
• InChIKey: HIJXKMHXOVKBEK-AOVQSLKQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(methoxycarbonyl)benzoyloxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(methoxycarbonyl)benzoyloxy]oxane-2-carboxylic acid
• Synonyms: 1-(Methyl 1,2-Benzenedicarboxylate) β-D-Glucopyranuronic Acid; Monomethylphthalate Glucuronide; Monomethyl Phthalate O-β-D-Glucuronide

Database IDs

• CAS Number: 53819-80-0
• PubChem SID: 164230354
• PubChem CID: 71750651

CALCULATED PROPERTIES

• Acid pKa: 2.771496
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.7790425
• LogD (pH = 7.4): -3.6097057
• Log P: -0.11348787
• Molar Refractivity: 77.6381 cm^3
• Polarizability: 31.096537 Å^3
• Polar Surface Area: 159.82 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M566545

A glucuronide conjugate of the phthalate ester metabolite Monomethyl Phthalate (M566540).

REFERENCES

• Thompson, R.M. et al.: Drug Metab. Disp., 1, 489 (1973)