2.0 2012-10-10 12:21:51 -0600 2015-09-13 15:15:34 -0600 ECMDB23201 M2MDB003591 Quercetin Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. In E. coli it is metabolized by Quercetin 2,3-dioxygenase. This enzyme catalyzes the reaction Quercetin + O2 = 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate + CO + H+. Quercetin is not a normal growth substrate for E. coli but it is found in high levels in the human gut. This enzyme may have evolved to break down quercitin to prevent its inhibition of key E. coli proteins, such as DNA gyrase. 2-(3,4-Dihydroxy-phenyl)-3,5,7-trihydroxy-chromen-4-one 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one 3',4',5,7-tetrahydroxy-3-methoxyflavone 3',4',5,7-Tetrahydroxyflavan-3-ol 3',4',5,7-tetrahydroxyflavon-3-ol 3,3',4',5,7-pentahydroxyflavone 3,3',4,5,7-Pentahydroxyflavone 3,4',5,5',7-pentahydroxy-Flavone 3,5,7,3',4'-Pentahydroxyflavone 3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-on 3-methoxy-5,7,3',4'-tetrahydroxyflavone 3-methoxyluteolin Flavin meletin Meletin Quercetin dihydrate Quercetin dihydric acid Quercetol Quertin Sophoretin Xanthaurine C15H10O7 302.2357 302.042652674 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one quercetin 117-39-5 OC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C(O)=C1 InChI=1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H REFJWTPEDVJJIY-UHFFFAOYSA-N Solid Membrane logp 1.81 ALOGPS logs -3.06 ALOGPS solubility 2.61e-01 g/l ALOGPS melting_point 316 - 318 C logp 2.16 ChemAxon pka_strongest_acidic 6.38 ChemAxon pka_strongest_basic -4 ChemAxon iupac 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one ChemAxon average_mass 302.2357 ChemAxon mono_mass 302.042652674 ChemAxon smiles OC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C(O)=C1 ChemAxon formula C15H10O7 ChemAxon inchi InChI=1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H ChemAxon inchikey REFJWTPEDVJJIY-UHFFFAOYSA-N ChemAxon polar_surface_area 127.45 ChemAxon refractivity 76.86 ChemAxon polarizability 28.54 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 2261 Specdb::CMs 5652 Specdb::CMs 31528 Specdb::CMs 38890 Specdb::CMs 175213 Specdb::NmrOneD 2026 Specdb::NmrOneD 166371 Specdb::NmrOneD 166675 Specdb::MsMs 2445 Specdb::MsMs 2446 Specdb::MsMs 2447 Specdb::MsMs 6061 Specdb::MsMs 6062 Specdb::MsMs 6063 Specdb::MsMs 6064 Specdb::MsMs 6065 Specdb::MsMs 6066 Specdb::MsMs 6067 Specdb::MsMs 6068 Specdb::MsMs 6069 Specdb::MsMs 6070 Specdb::MsMs 6071 Specdb::MsMs 6072 Specdb::MsMs 180057 Specdb::MsMs 180058 Specdb::MsMs 180059 Specdb::MsMs 182391 Specdb::MsMs 182392 Specdb::MsMs 182393 Specdb::MsMs 285598 Specdb::MsMs 285599 Specdb::MsMs 285600 Specdb::MsMs 285601 Specdb::NmrTwoD 1961 HMDB05794 5280343 C00389 16243 3457-TETRAHYDROXY-3-METHOXYFLAVONE QUE Quercetin FDB011904 Perez-Vizcaino F, Duarte J, Andriantsitohaina R: Endothelial function and cardiovascular disease: effects of quercetin and wine polyphenols. Free Radic Res. 2006 Oct;40(10):1054-65. 17015250 Krewson, Charles F. Colloidal flavonols. (1953), US 2637725 19530505 CAN 47:42700 AN 1953:42700 http://hmdb.ca/system/metabolites/msds/000/005/001/original/HMDB05794.pdf?1358463275 Quercetin + Oxygen > 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate + CO + Hydrogen ion