(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(2H3)methyl(2H4)phenoxy]oxane-2-carboxylic acid

• ChemBase ID: 165032
• Molecular Formular: C13H16O7
• Molecular Mass: 284.26194
• Monoisotopic Mass: 284.08960285
• SMILES: c1(O[C@@H]2O[C@H]([C@H]([C@@H]([C@@H]2O)O)O)C(=O)O)c(cccc1)C
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2ccccc2C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C13H16O7/c1-6-4-2-3-5-7(6)19-13-10(16)8(14)9(15)11(20-13)12(17)18/h2-5,8-11,13-16H,1H3,(H,17,18)/t8-,9-,10+,11-,13+/m0/s1
• InChIKey: UPSZSICMSBXXRN-XPORZQOISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(^2H₃)methyl(^2H₄)phenoxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(^2H₃)methyl(^2H₄)phenoxy]oxane-2-carboxylic acid
• Synonyms: 2-Methylphenyl β-D-Glucopyranosiduronic Acid; o-Cresol β-D-Glucuronide

Database IDs

• CAS Number: 111897-99-5
• PubChem SID: 162259165
• PubChem CID: 71315005

CALCULATED PROPERTIES

• Acid pKa: 3.4803712
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.7752293
• LogD (pH = 7.4): -3.1458533
• Log P: 0.23530833
• Molar Refractivity: 65.0919 cm^3
• Polarizability: 26.426935 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 147-149°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C782000

A metabolite of o-Cresol.

REFERENCES

• Goerge, G., et al.: Xenobiotica, 17, 1293 (1987)