(2R,3R,4R,5S,6R)-6-[4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 175005
• Molecular Formular: C21H20O11
• Molecular Mass: 448.3769
• Monoisotopic Mass: 448.10056146
• SMILES: c1c(cc(c2c1OC(CC2=O)c1ccc(cc1)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)O)O
• Canonical SMILES: Oc1cc2OC(CC(=O)c2c(c1)O)c1ccc(cc1)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C21H20O11/c22-9-5-11(23)15-12(24)7-13(31-14(15)6-9)8-1-3-10(4-2-8)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+/m1/s1
• InChIKey: DFIUUCDSSKATFP-TXBPIPTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-[4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-[4-(5,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4-[(2S)-3,4-Dihydro-5,7-dihydroxy-4-oxo-2H-1-benzopyran-2-yl]phenyl β-D-Glucopyranosiduronic Acid; Naringenin-4'-O-β-D-glucuronopyranoside; Naringenin-4’-glucuronide; Naringenin 4'-O-β-D-Glucuronide(Mixture of Diastereomers)

Database IDs

• CAS Number: 158196-35-1
• PubChem SID: 164230915
• PubChem CID: 71750945

CALCULATED PROPERTIES

• Acid pKa: 3.2136269
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -1.3787895
• LogD (pH = 7.4): -2.6690085
• Log P: 0.8873145
• Molar Refractivity: 103.3016 cm^3
• Polarizability: 41.01034 Å^3
• Polar Surface Area: 183.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N378960

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)