2.0 2012-10-10 12:22:01 -0600 2015-06-03 17:26:09 -0600 ECMDB23205 M2MDB003595 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate is an intermediate in the degradation of quercetin by E. coli. 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. 2,4DiOH-6(2,4DiOHBenAcid)BenzAcid 2-(3,4-Dihydroxybenzoyl)oxy-4,6-dihydroxybenzoate 2-(3,4-Dihydroxybenzoyl)oxy-4,6-dihydroxybenzoic acid 2-(3,4-Dihydroxybenzoyloxy)-4,6-dihydroxybenzoate 2-(3,4-Dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid 2-Protocatechoylphloroglucinolcarboxylate 2-Protocatechoylphloroglucinolcarboxylic acid 2-Protocatechuoyl phloroglucinolcarboxylate 2-Protocatechuoyl phloroglucinolcarboxylic acid C14H10O8 306.2244 306.037567296 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid OC(=O)C1=C(O)C=C(O)C=C1OC(=O)C1=CC(O)=C(O)C=C1 InChI=1S/C14H10O8/c15-7-4-10(18)12(13(19)20)11(5-7)22-14(21)6-1-2-8(16)9(17)3-6/h1-5,15-18H,(H,19,20) GRXIELRCPYIEQI-UHFFFAOYSA-N Membrane logp 2.47 ALOGPS logs -3.12 ALOGPS solubility 2.31e-01 g/l ALOGPS logp 2.73 ChemAxon pka_strongest_acidic 2.45 ChemAxon pka_strongest_basic -5.8 ChemAxon iupac 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid ChemAxon average_mass 306.2244 ChemAxon mono_mass 306.037567296 ChemAxon smiles OC(=O)C1=C(O)C=C(O)C=C1OC(=O)C1=CC(O)=C(O)C=C1 ChemAxon formula C14H10O8 ChemAxon inchi InChI=1S/C14H10O8/c15-7-4-10(18)12(13(19)20)11(5-7)22-14(21)6-1-2-8(16)9(17)3-6/h1-5,15-18H,(H,19,20) ChemAxon inchikey GRXIELRCPYIEQI-UHFFFAOYSA-N ChemAxon polar_surface_area 144.52 ChemAxon refractivity 73.04 ChemAxon polarizability 27.89 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 33196 Specdb::CMs 47840 Specdb::CMs 172057 Specdb::NmrOneD 269618 Specdb::NmrOneD 269619 Specdb::NmrOneD 269620 Specdb::NmrOneD 269621 Specdb::NmrOneD 269622 Specdb::NmrOneD 269623 Specdb::NmrOneD 269624 Specdb::NmrOneD 269625 Specdb::NmrOneD 269626 Specdb::NmrOneD 269627 Specdb::NmrOneD 269628 Specdb::NmrOneD 269629 Specdb::NmrOneD 269630 Specdb::NmrOneD 269631 Specdb::NmrOneD 269632 Specdb::NmrOneD 269633 Specdb::NmrOneD 269634 Specdb::NmrOneD 269635 Specdb::NmrOneD 269636 Specdb::NmrOneD 269637 Specdb::MsMs 26861 Specdb::MsMs 26862 Specdb::MsMs 26863 Specdb::MsMs 33419 Specdb::MsMs 33420 Specdb::MsMs 33421 Specdb::MsMs 2405231 Specdb::MsMs 2405232 Specdb::MsMs 2405233 Specdb::MsMs 2530680 Specdb::MsMs 2530681 Specdb::MsMs 2530682 C04524 16068 Quercetin + Oxygen > 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate + CO + Hydrogen ion