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

• ChemBase ID: 174322
• Molecular Formular: C15H18O9
• Molecular Mass: 342.29802
• Monoisotopic Mass: 342.09508216
• SMILES: O1[C@@H](Oc2ccccc2C(=O)OC)[C@@H](O)[C@H]([C@@H]([C@@H]1C(=O)OC)O)O
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccccc2C(=O)OC)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H18O9/c1-21-13(19)7-5-3-4-6-8(7)23-15-11(18)9(16)10(17)12(24-15)14(20)22-2/h3-6,9-12,15-18H,1-2H3/t9-,10-,11+,12-,15+/m0/s1
• InChIKey: LDORTLMDVQBDPM-QKZHPOIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(methoxycarbonyl)phenoxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(methoxycarbonyl)phenoxy]oxane-2-carboxylate
• Synonyms: 2-(Μethoxycarbonyl)phenyl β-D-Glucopyranosiduronic Αcid Μethyl Εster; Methyl Salicylate β-D-O-Glucuronide Methyl Ester

Database IDs

• CAS Number: 226932-59-8
• PubChem SID: 164230232
• PubChem CID: 71750605

CALCULATED PROPERTIES

• Acid pKa: 12.165672
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.12874213
• LogD (pH = 7.4): -0.12874949
• Log P: -0.12874204
• Molar Refractivity: 76.8451 cm^3
• Polarizability: 31.1672 Å^3
• Polar Surface Area: 131.75 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Off-White Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M326585

Intermediate in the synthesis of Aspirin metabolite.

REFERENCES

• Grootveld, M., et al.: Biochem. Pharmacol., 37, 271 (1988)
• Subbegowda, R., et al.: Cancer Res., 58, 2772 (1988)
• Yoshida, Y., et al.: Eur. J. Pharmacol., 349, 49 (1988)