(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 169887
• Molecular Formular: C22H22O12
• Molecular Mass: 478.40288
• Monoisotopic Mass: 478.11112614
• SMILES: c1(cc(c2c(c1)O[C@@H](CC2=O)c1cc(c(cc1)OC)O)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: COc1ccc(cc1O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C22H22O12/c1-31-13-3-2-8(4-10(13)23)14-7-12(25)16-11(24)5-9(6-15(16)33-14)32-22-19(28)17(26)18(27)20(34-22)21(29)30/h2-6,14,17-20,22-24,26-28H,7H2,1H3,(H,29,30)/t14-,17-,18-,19+,20-,22+/m0/s1
• InChIKey: NEAWXAXVQDDFJL-QBUJOIIVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (2S)-3,4-Dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-2H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid; Hesperetin 7-O-β-D-Glucuronide

Database IDs

• CAS Number: 67322-08-1
• PubChem SID: 162264019
• PubChem CID: 56598869

CALCULATED PROPERTIES

• Acid pKa: 2.7317145
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -1.9700118
• LogD (pH = 7.4): -2.772689
• Log P: 0.7296432
• Molar Refractivity: 109.7648 cm^3
• Polarizability: 43.57143 Å^3
• Polar Surface Area: 192.44 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Yellow Solid
• Melting Point: 189-192°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H289510

A metabolite of Hesperetin (H289500), the main circulating metabolite involved in osteoblast differentiation.

REFERENCES

• Kim, D., et al.: J. Cell Biochem., 101, 790 (2007)
• Brand, W., et al.: Drug Metab. Dispos., 36, 1794 (2007)