methyl (2S,3S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

• ChemBase ID: 173742
• Molecular Formular: C7H12O7
• Molecular Mass: 208.16598
• Monoisotopic Mass: 208.05830272
• SMILES: O1C([C@H](C([C@@H]([C@@H]1C(=O)OC)O)O)O)O
• Canonical SMILES: COC(=O)[C@@H]1OC(O)[C@H](C([C@@H]1O)O)O
• InChI: InChI=1S/C7H12O7/c1-13-7(12)5-3(9)2(8)4(10)6(11)14-5/h2-6,8-11H,1H3/t2?,3-,4+,5-,6?/m0/s1
• InChIKey: DICCNWCUKCYGNF-CQGHMCOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
• Synonyms: D-Glucuronic Acid Methyl Ester; Methyl D-Glucuronate

Database IDs

• CAS Number: 52613-19-1
• PubChem SID: 164229652
• PubChem CID: 71750362

CALCULATED PROPERTIES

• Acid pKa: 11.283209
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.4663713
• LogD (pH = 7.4): -2.4664273
• Log P: -2.4663706
• Molar Refractivity: 40.5599 cm^3
• Polarizability: 17.211765 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M311540

Protected D-Glucuronide.

REFERENCES

• Smith, P., et al.: Biochem. Pharmacol., 44, 1661 (1992)