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

• ChemBase ID: 175022
• Molecular Formular: C21H20O11
• Molecular Mass: 448.3769
• Monoisotopic Mass: 448.10056146
• SMILES: c1c(cc(c2c1O[C@@H](CC2=O)c1ccc(cc1)O)O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2cc3O[C@@H](CC(=O)c3c(c2)O)c2ccc(cc2)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H20O11/c22-9-3-1-8(2-4-9)13-7-12(24)15-11(23)5-10(6-14(15)31-13)30-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-6,13,16-19,21-23,25-27H,7H2,(H,28,29)/t13-,16-,17-,18+,19-,21+/m0/s1
• InChIKey: BDCRTIDKZGEVEN-CGXGPNJMSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 158196-34-0
• PubChem SID: 164230932
• PubChem CID: 15540754

CALCULATED PROPERTIES

• Acid pKa: 2.731715
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -1.8123643
• LogD (pH = 7.4): -2.6169245
• Log P: 0.8873145
• Molar Refractivity: 103.3016 cm^3
• Polarizability: 41.010445 Å^3
• Polar Surface Area: 183.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N378965

A metabolite of Naringenin (N378950).

REFERENCES

• Berrin, J., et al.: Biochem. J., 373, 41 (2003)
• O'Leary, K., et al.: Biochem. Pharmacol., 65, 479 (2003)
• Hirata, A., et al.: Anticancer Res., 25, 3367 (2003)