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

• ChemBase ID: 167774
• Molecular Formular: C13H14O10
• Molecular Mass: 330.24426
• Monoisotopic Mass: 330.05869665
• SMILES: c1(cc(cc(c1)C(=O)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)O
• Canonical SMILES: Oc1cc(O[C@@H]2O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]2O)O)O)cc(c1)C(=O)O
• InChI: InChI=1S/C13H14O10/c14-5-1-4(11(18)19)2-6(3-5)22-13-9(17)7(15)8(16)10(23-13)12(20)21/h1-3,7-10,13-17H,(H,18,19)(H,20,21)/t7-,8-,9+,10-,13+/m0/s1
• InChIKey: LEONNYUSLXUBTI-CDHFTJPESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-(3-carboxy-5-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-(3-carboxy-5-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: α-Resorcylic Acid 3-O-β-D-Glucuronide; 5-Carboxyresorcinol 3-O-β-D-Glucuronide; 3,5-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide

Database IDs

• PubChem SID: 162261907
• PubChem CID: 71316223

CALCULATED PROPERTIES

• Acid pKa: 2.7018237
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -5.4953465
• LogD (pH = 7.4): -7.768213
• Log P: -0.92409545
• Molar Refractivity: 69.2878 cm^3
• Polarizability: 27.787466 Å^3
• Polar Surface Area: 173.98 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >145°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - D451705

3,5-Dihydroxybenzoic Acid 3-O-β-D-Glucuronide is a possible glucuronide metabolite of alkylresorcinol in humans.