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

• ChemBase ID: 174737
• Molecular Formular: C16H18O10
• Molecular Mass: 370.30812
• Monoisotopic Mass: 370.08999678
• SMILES: c1ccc(c(c1)C(=O)OCC)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CCOC(=O)c1ccccc1C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H18O10/c1-2-24-14(22)7-5-3-4-6-8(7)15(23)26-16-11(19)9(17)10(18)12(25-16)13(20)21/h3-6,9-12,16-19H,2H2,1H3,(H,20,21)/t9-,10-,11+,12-,16-/m0/s1
• InChIKey: MCMQAADVCDNUCU-RPHNGCRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[2-(ethoxycarbonyl)benzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[2-(ethoxycarbonyl)benzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-(Ethyl 1,2-Benzenedicarboxylate) β-D-Glucopyranuronic Acid; Monoethyl Phthalate O-β-D-Glucuronide

Database IDs

• CAS Number: 671215-25-1
• PubChem SID: 164230647
• PubChem CID: 71750794

CALCULATED PROPERTIES

• Acid pKa: 2.7712727
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.422427
• LogD (pH = 7.4): -3.2529142
• Log P: 0.2433201
• Molar Refractivity: 82.3867 cm^3
• Polarizability: 32.90421 Å^3
• Polar Surface Area: 159.82 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M542585

A glucuronide conjugate of the phthalate metabolite Monoethyl Phthalate (M542585).

REFERENCES

• Silva, M.J. et all.: Arch. Toxicol., 77, 561 (2003)
• Samandar, E. et al.: Env. Res., 109, 641 (2003)