(2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 177235
• Molecular Formular: C21H18O13
• Molecular Mass: 478.35982
• Monoisotopic Mass: 478.07474064
• SMILES: c1(cc(c2c(c1)oc(c(c2=O)O)c1cc(c(cc1)O)O)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(c(c3=O)O)c2ccc(c(c2)O)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H18O13/c22-8-2-1-6(3-9(8)23)18-15(27)13(25)12-10(24)4-7(5-11(12)33-18)32-21-17(29)14(26)16(28)19(34-21)20(30)31/h1-5,14,16-17,19,21-24,26-29H,(H,30,31)/t14-,16-,17+,19-,21+/m0/s1
• InChIKey: JXWGCVLNCGCZRU-JENRNSKYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-(3,4-Dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid; Quercetin 7-O-β-Glucuronide; Quercetin 7-Glucuronide; Quercetin 7-O-β-D-Glucuronide

Database IDs

• CAS Number: 38934-20-2
• PubChem SID: 164233145
• PubChem CID: 11641481

CALCULATED PROPERTIES

• Acid pKa: 2.7202358
• H Acceptors: 13
• H Donor: 8
• LogD (pH = 5.5): -2.5022864
• LogD (pH = 7.4): -3.396763
• Log P: 0.20850591
• Molar Refractivity: 108.874 cm^3
• Polarizability: 42.191887 Å^3
• Polar Surface Area: 223.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - Q509515

Quercetin 3-O-β-D-Glucuronide is a metabolite of Quercetin (Q509500).

REFERENCES

• Ajay, M., et al.: Life Sci., 74, 603 (2003)
• Shen, S., et al.: Toxicol. Appl. Pharmacol., 197, 84 (2003)
• Amira, S., et al.: Eur. J. Pharmacol. 599, 126 (2003)