(2S,3S,4S,5R,6S)-6-(2-carboxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 177680
• Molecular Formular: C13H14O9
• Molecular Mass: 314.24486
• Monoisotopic Mass: 314.06378203
• SMILES: [C@@H]1(Oc2ccccc2C(=O)O)O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@@H](O[C@H]([C@H]1O)C(=O)O)Oc1ccccc1C(=O)O
• InChI: InChI=1S/C13H14O9/c14-7-8(15)10(12(19)20)22-13(9(7)16)21-6-4-2-1-3-5(6)11(17)18/h1-4,7-10,13-16H,(H,17,18)(H,19,20)/t7-,8-,9+,10-,13+/m0/s1
• InChIKey: JSCWDKKMLIQCMR-CDHFTJPESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-(2-carboxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: 1-salicylate glucuronide
• Synonyms: 2-Carboxyphenyl β-D-Glucopyranosiduronic Acid; o-Carboxypheny β-D-Glucopyranosiduronic Acid; Salicylic Acid Glucuronide; Salicylic Acid Phenolic Glucuronide; Salicylic Glucuronide; Salicylic Acid β-D-O-Glucuronide

Database IDs

• CAS Number: 7695-70-7
• PubChem SID: 164233590
• PubChem CID: 3084023

CALCULATED PROPERTIES

• Acid pKa: 2.9002528
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -4.6792626
• LogD (pH = 7.4): -7.279532
• Log P: -0.6205301
• Molar Refractivity: 67.3069 cm^3
• Polarizability: 27.089005 Å^3
• Polar Surface Area: 153.75 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 131-133°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - S088130

Salicylic Acid β-D-O-Glucuronide is a metabolite of Acetylsalicylic Acid (Aspirin) (A187780).

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)