Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H10O7 |
Molecular Weight | 302.2357 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C3=CC(O)=C(O)C=C3
InChI
InChIKey=REFJWTPEDVJJIY-UHFFFAOYSA-N
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
Quercetin is a unique bioflavonoid that has been extensively studied by researchers over the past 30 years. Quercetin, the most abundant of the flavonoids (the name comes from the Latin –quercetum, meaning oak forest, quercus oak) consists of 3 rings and 5 hydroxyl groups. Quercetin is a member of the class of flavonoids called flavonoles and forms the backbone for many other flavonoids including the citrus flavonoids like rutin, hesperidins, Naringenin and tangeritin. It is widely distributed in the plant kingdom in rinds and barks. The best described property of Quercetin is its ability to act as antioxidant. Quercetin seems to be the most powerful flavonoids for protecting the body against reactive oxygen species, produced during the normal oxygen metabolism or are induced by exogenous damage [9, 10]. One of the most important mechanisms and the sequence of events by which free radicals interfere with the cellular functions seem to be the lipid peroxidation leading eventually the cell death. To protect this cellular death to happen from reactive oxygen species, living organisms have developed antioxidant line of defense systems [11]. These include enzymatic and non-enzymatic antioxidants that keep in check ROS/RNS level and repair oxidative cellular damage. The major enzymes, constituting the first line of defence, directly involved in the neutralization of ROS/RNS are: superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GPx) The second line of defence is represented by radical scavenging antioxidants such as vitamin C, vitamin A and plant phytochemicals including quercetin that inhibit the oxidation chain initiation and prevent chain propagation. This may also include the termination of a chain by the reaction of two radicals. The repair and de novo enzymes act as the third line of defence by repairing damage and reconstituting membranes. These include lipases, proteases, DNA repair enzymes and transferases. Quercetin is a specific quinone reductase 2 (QR2) inhibitor, an enzyme (along with the human QR1 homolog) which catalyzes metabolism of toxic quinolines. Inhibition of QR2 in plasmodium may potentially cause lethal oxidative stress. The inhibition of antioxidant activity in plasmodium may contribute to killing the malaria causing parasites.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26512639
Curator's Comment: There is limited ability of the reviewed flavonoids to access the brain
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28528183 |
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Target ID: GO:0072593 |
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Target ID: CHEMBL4528 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28433637 |
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Target ID: CHEMBL1973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28273864 |
14.29 nM [IC50] | ||
Target ID: Phospholipase A2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28256049 |
1.36 µM [IC50] | ||
Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17724002 |
113.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
500 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9816216/ |
630 mg/m² single, intravenous dose: 630 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
QUERCETIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2077 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9816216/ |
630 mg/m² single, intravenous dose: 630 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
QUERCETIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
47 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9816216/ |
630 mg/m² single, intravenous dose: 630 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
QUERCETIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
moderate [IC50 11.6 uM] | ||||
moderate to strong [IC50 5.5 uM] | ||||
modest [Ki 10.1 uM] | ||||
no | ||||
not significant [IC50 104 uM] | ||||
not significant [IC50 151 uM] | no (pharmacogenomic study) Comment: drug inhibits caffeine metabolism, which is unrelated to CYP1A2*1C and *1F gene polymorphisms (https://www.hindawi.com/journals/bmri/2014/405071/) |
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potent [IC50 0.65 uM] | ||||
yes [IC50 15.9 uM] | weak (co-administration study) Comment: AUC increase of 24%, Cmax increase of 31% |
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yes [IC50 4.22 uM] | yes (co-administration study) Comment: 1.8-fold increase in AUC8h and 1.5 fold increase in Cmax |
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yes [IC50 8 uM] | ||||
yes [IC50 8.1 uM] | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | no (co-administration study) Comment: 133% induction at 50 uM of drug; see https://www.sciencedirect.com/science/article/pii/S1818087618305154#bib0013 for in vivo study |
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Page: 5.0 |
yes | weak (co-administration study) Comment: decreased enzyme activity by 10.4% Page: 5.0 |
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Page: 1.0 |
yes | weak (co-administration study) Comment: increased enzyme activity by 25.3% Page: 1.0 |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
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Influence of quercetin on B16 melanotic melanoma growth in C57BL/6 mice and on activity of some acid hydrolases in melanoma tissue. | 2001 |
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Protective effect of phenolic compounds isolated from the hooks and stems of Uncaria sinensis on glutamate-induced neuronal death. | 2001 |
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Electrospray ionisation mass spectrometric study of degradation products of quercetin, quercetin-3-glucoside and quercetin-3-rhamnoglucoside, produced by in vitro fermentation with human faecal flora. | 2001 |
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Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus. | 2001 Apr |
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Constituents of Afzelia bella stem bark. | 2001 Apr |
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Kaempferide triglycoside: a possible factor of resistance of carnation (Dianthus caryophyllus) to Fusarium oxysporum f. sp. dianthi. | 2001 Apr |
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Evaluation of polyphenolic and flavonoid compounds in honeybee-collected pollen produced in Spain. | 2001 Apr |
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Measurement of copper-binding sites on low density lipoprotein. | 2001 Apr |
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Structure-activity study on the quinone/quinone methide chemistry of flavonoids. | 2001 Apr |
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Natural therapies for ocular disorders, part two: cataracts and glaucoma. | 2001 Apr |
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Effect of five flavonoid compounds isolated from Quercus dentata Thunb on superoxide generation in human neutrophils and phosphorylation of neutrophil proteins. | 2001 Apr |
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Modulation of cisplatin cytotoxicity and cisplatin-induced DNA cross-links in HepG2 cells by regulation of glutathione-related mechanisms. | 2001 Apr |
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Ca2+-induced contraction of cat esophageal circular smooth muscle cells. | 2001 Apr |
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Identification of quercetin glucuronides in human plasma by high-performance liquid chromatography-tandem mass spectrometry. | 2001 Apr 5 |
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Pre-clinical and clinical study of QC12, a water-soluble, pro-drug of quercetin. | 2001 Feb |
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A malonylated anthocyanin and flavonols in blue Meconopsis flowers. | 2001 Feb |
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Guaiane dimers from Xylopia vielana. | 2001 Feb |
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Protective effects of flavonoids in the roots of Scutellaria baicalensis Georgi against hydrogen peroxide-induced oxidative stress in HS-SY5Y cells. | 2001 Feb |
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Reduction of dehydroascorbic acid by homocysteine. | 2001 Feb 16 |
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Separation of kaempferols in Impatients balsamina flowers by capillary electrophoresis with electrochemical detection. | 2001 Feb 16 |
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Pharmacological interventions of cyanide-induced cytotoxicity and DNA damage in isolated rat thymocytes and their protective efficacy in vivo. | 2001 Feb 3 |
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Induction of human NAD(P)H:quinone oxidoreductase (NQO1) gene expression by the flavonol quercetin. | 2001 Feb 3 |
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[Polyphenol compounds from Hamamelis virginiana L]. | 2001 Jan |
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Characterization of enzymes participating in carbonyl reduction of 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in human placenta. | 2001 Jan 30 |
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Interaction of sheep liver cytosolic aldehyde dehydrogenase with quercetin, resveratrol and diethylstilbestrol. | 2001 Jan 30 |
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Noni plant may help TB. | 2001 Mar |
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Presence of aldose reductase inhibitors in tea leaves. | 2001 Mar |
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Enhanced antioxidant activity after chlorination of quercetin by hypochlorous acid. | 2001 Mar |
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Flavonoids and phenylpropanoid derivatives from Campanula barbata. | 2001 Mar |
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Treatment of interstitial cystitis with a quercetin supplement. | 2001 Mar |
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Chemoprotective potentials of homoisoflavonoids and chalcones of Dracaena cinnabari: modulations of drug-metabolizing enzymes and antioxidant activity. | 2001 Mar |
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Addition of milk does not affect the absorption of flavonols from tea in man. | 2001 Mar |
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Flavonoid characters contributing to the taxonomic revision of the Hebe parviflora complex. | 2001 Mar |
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Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. | 2001 Mar |
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Relationship between effects of phenolic compounds on the generation of free radicals from lactoperoxidase-catalyzed oxidation of NAD(P)H or GSH and their DPPH scavenging ability. | 2001 Mar |
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Simultaneous determination of quercetin, kaempferol and (E)-cinnamic acid in vegetative organs of Schisandra chinensis Baill. by HPLC. | 2001 Mar |
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Protective effect of various antioxidants on the toxicity of sulphur mustard administered to mice by inhalation or percutaneous routes. | 2001 Mar 14 |
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Detection of drug-induced, superoxide-mediated cell damage and its prevention by antioxidants. | 2001 Mar 15 |
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Determination of phenolic acids and flavonoids of apple and pear by high-performance liquid chromatography. | 2001 Mar 2 |
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Effects of simple aromatic compounds and flavonoids on Ca2+ fluxes in rat pituitary GH(4)C(1) cells. | 2001 Mar 2 |
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Bioactive chemical constituents from Alchornea laxiflora (benth) pax and hoffman. | 2001 Mar 3 |
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Antihypertensive effects of the flavonoid quercetin in spontaneously hypertensive rats. | 2001 May |
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Fast repair of the radical cations of dCMP and poly C by quercetin and rutin. | 2001 May |
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Induction of stress response proteins and experimental renal ischemia/reperfusion. | 2001 May |
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Influence of prenylated and non-prenylated flavonoids on liver microsomal lipid peroxidation and oxidative injury in rat hepatocytes. | 2001 May |
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Modulation of multidrug resistance protein 1 (MRP1/ABCC1) transport and atpase activities by interaction with dietary flavonoids. | 2001 May |
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PI3K inhibitors reverse the suppressive actions of insulin on CYP2E1 expression by activating stress-response pathways in primary rat hepatocytes. | 2001 May |
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Structural damage to proteins caused by free radicals: asessment, protection by antioxidants, and influence of protein binding. | 2001 May 15 |
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Effects of structurally related flavonoids on cell cycle progression of human melanoma cells: regulation of cyclin-dependent kinases CDK2 and CDK1. | 2001 May 15 |
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Suppression of inducible cyclooxygenase and nitric oxide synthase through activation of peroxisome proliferator-activated receptor-gamma by flavonoids in mouse macrophages. | 2001 May 4 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01708278
COPD Subjects will be asked to avoid quercetin rich diet for one week and then asked to take one of the following for 1 week
Quercetin 500 mg/350 mg of vitamin C and 10 mg niacin
Quercetin 1000 mg/350 mg of vitamin C and 10 mg niacin
Quercetin 2000 mg/350 mg of vitamin C and 10 mg niacin
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28079005
DCs, exposed to 25uM quercetin, activate a pattern of genes that increase extracellular iron export, resulting in an overall decrease in the intracellular iron content and consequent diminished inflammatory abilities.
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
664018
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DSLD |
1099 (Number of products:1551)
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LIVERTOX |
NBK556474
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3514
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DTXSID4021218
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D011794
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100000079143
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m9420
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SUB15072MIG
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204-187-1
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5280343
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C792
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QUERCETIN
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3529
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C401828
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DB04216
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57694
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ACTIVE MOIETY
METABOLITE (PARENT)
PRODRUG (METABOLITE ACTIVE)