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Record Information
Version	2.0
Creation Date	2012-10-10 12:22:01 -0600
Update Date	2015-06-03 17:26:09 -0600
Secondary Accession Numbers	ECMDB23205
Identification
Name:	2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate
Description	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.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaf3b01c8> Close
Synonyms:	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
Chemical Formula:	C14H10O8
Weight:	Average: 306.2244 Monoisotopic: 306.037567296
InChI Key:	GRXIELRCPYIEQI-UHFFFAOYSA-N
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)
CAS number:	Not Available
IUPAC Name:	2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid
Traditional IUPAC Name:	2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid
SMILES:	OC(=O)C1=C(O)C=C(O)C=C1OC(=O)C1=CC(O)=C(O)C=C1
Chemical Taxonomy
Description	belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
Kingdom	Organic compounds
Super Class	Phenylpropanoids and polyketides
Class	Depsides and depsidones
Sub Class	Not Available
Direct Parent	Depsides and depsidones
Alternative Parents	p-Hydroxybenzoic acid esters m-Hydroxybenzoic acid esters Salicylic acids Phenol esters Benzoic acids Resorcinols Phenoxy compounds Catechols Benzoyl derivatives 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Dicarboxylic acids and derivatives Vinylogous acids Carboxylic acid esters Carboxylic acids Hydrocarbon derivatives Organic oxides Organooxygen compounds
Substituents	Depside backbone M-hydroxybenzoic acid ester P-hydroxybenzoic acid ester Dihydroxybenzoic acid Hydroxybenzoic acid Phenol ester Salicylic acid or derivatives Salicylic acid Benzoate ester Benzoic acid Benzoic acid or derivatives Phenoxy compound Resorcinol Catechol Benzoyl Phenol 1-hydroxy-4-unsubstituted benzenoid 1-hydroxy-2-unsubstituted benzenoid Benzenoid Dicarboxylic acid or derivatives Monocyclic benzene moiety Vinylogous acid Carboxylic acid ester Carboxylic acid derivative Carboxylic acid Organooxygen compound Hydrocarbon derivative Organic oxide Organic oxygen compound Aromatic homomonocyclic compound
Molecular Framework	Aromatic homomonocyclic compounds
External Descriptors	benzoate ester (CHEBI:16068 ) dihydroxybenzoic acid (CHEBI:16068 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.23 g/L ALOGPS logP 2.47 ALOGPS logP 2.73 ChemAxon logS -3.1 ALOGPS pKa (Strongest Acidic) 2.45 ChemAxon pKa (Strongest Basic) -5.8 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 144.52 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 73.04 m³·mol⁻¹ ChemAxon Polarizability 27.89 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Quercetin + Oxygen > 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate + CO + Hydrogen ion
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-000i-0900000000-f063a50e2100260c680c View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive splash10-001i-0090011000-57d471b57e310ee50676 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-052r-0596000000-47902ef3296c1477004b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0961000000-40a68d3f3894906dba7a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0019-5910000000-8ede257c8c7d14f1a891 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-08fr-0194000000-f4af9d9f87266faff042 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-03di-0290000000-38a97201178b58d10cd5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-06a0-3920000000-6ab6758b580e79a6a45d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-0692000000-5556817bba47ece0212f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0950000000-c9c6bed2b1d180ffeb22 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0f79-3930000000-ff1140404484c2ffa85f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0fb9-0900000000-95ab0e687e19e8f7f0c4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-07gi-0970000000-2eaec82c823970bda725 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0fbc-3930000000-658b94bc5d3ab0cd21a8 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 16068 HMDB ID HMDB0059651 Pubchem Compound ID 440370 Kegg ID C04524 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available