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

• ChemBase ID: 159447
• Molecular Formular: C15H16O10
• Molecular Mass: 356.28154
• Monoisotopic Mass: 356.07434671
• SMILES: c1(ccccc1OC(=O)C)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CC(=O)Oc1ccccc1C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H16O10/c1-6(16)23-8-5-3-2-4-7(8)14(22)25-15-11(19)9(17)10(18)12(24-15)13(20)21/h2-5,9-12,15,17-19H,1H3,(H,20,21)/t9-,10-,11+,12-,15-/m0/s1
• InChIKey: VHJPVKQXMOFZPM-HJHSNUOESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[2-(acetyloxy)benzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[2-(acetyloxy)benzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[2-(Acetyloxy)benzoate] β-D-Glucopyranuronic Acid; 1-Salicylate Monoacetate β-D-Glucopyranuronic Acid; Aspirin-acyl-β-D-glucuronide; Acetylsalicylic Acid Acyl-β-D-glucuronide

Database IDs

• CAS Number: 24719-72-0
• PubChem SID: 162253582
• PubChem CID: 29971035

CALCULATED PROPERTIES

• Acid pKa: 2.8784554
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.0816672
• LogD (pH = 7.4): -3.9970722
• Log P: -0.5097039
• Molar Refractivity: 76.7452 cm^3
• Polarizability: 31.102627 Å^3
• Polar Surface Area: 159.82 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 145-147°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - A187775

A significant metabolite of Salicylic acid (SA) and Aspirin.

REFERENCES

• Dickinson, R.G., et al.: Biochem. Pharmacol., 47, 469 (1994)