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
| Molecular Formula | C15H10O7 |
| Molecular Weight | 302.2357 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0006927 |
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Target ID: CHEMBL4528 |
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Target ID: CHEMBL1973 |
14.29 nM [IC50] | ||
Target ID: Phospholipase A2 |
1.36 µM [IC50] | ||
Target ID: CHEMBL242 |
113.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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 |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
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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| yes | weak (co-administration study) Comment: decreased enzyme activity by 10.4% Page: 5.0 |
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| 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 |
|---|---|---|
| A new concept of tumor promotion by tumor necrosis factor-alpha, and cancer preventive agents (-)-epigallocatechin gallate and green tea--a review. | 2000 |
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| Oxidative stress involvement in chemically induced differentiation of K562 cells. | 2000 Jan 1 |
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| Upstream regulatory elements in chick heme oxygenase-1 promoter: a study in primary cultures of chick embryo liver cells. | 2000 Jun |
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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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| 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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| Induced cytoskeletal changes in bovine pulmonary artery endothelial cells by resveratrol and the accompanying modified responses to arterial shear stress. | 2001 |
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| Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus. | 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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| Identification of quercetin glucuronides in human plasma by high-performance liquid chromatography-tandem mass spectrometry. | 2001 Apr 5 |
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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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| Polyphyenolics increase t-PA and u-PA gene transcription in cultured human endothelial cells. | 2001 Feb |
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| The etiologies, pathophysiology, and alternative/complementary treatment of asthma. | 2001 Feb |
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| Activity of plant flavonoids against antibiotic-resistant bacteria. | 2001 Feb |
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| Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin: glutathione oxidation and conjugation. | 2001 Feb 15 |
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| Reduction of dehydroascorbic acid by homocysteine. | 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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| [Polyphenol compounds from Hamamelis virginiana L]. | 2001 Jan |
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| Antibacterial action of tryptanthrin and kaempferol, isolated from the indigo plant (Polygonum tinctorium Lour.), against Helicobacter pylori-infected Mongolian gerbils. | 2001 Jan |
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| Phenolic constituents of Phenax angustifolius. | 2001 Jan |
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| Neuroprotective constituents from Hedyotis diffusa. | 2001 Jan |
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| Studies on the effects of lactate transport inhibition, pyruvate, glucose and glutamine on amino acid, lactate and glucose release from the ischemic rat cerebral cortex. | 2001 Jan |
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| A method for the simultaneous evaluation of the activities of seven major human drug-metabolizing cytochrome P450s using an in vitro cocktail of probe substrates and fast gradient liquid chromatography tandem mass spectrometry. | 2001 Jan |
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| Luteolin inhibits an endotoxin-stimulated phosphorylation cascade and proinflammatory cytokine production in macrophages. | 2001 Jan |
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| Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids in macrophage J774A.1. | 2001 Jan 12 |
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| Searching for the physiological function of 17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: studies of substrate specificity and expression analysis. | 2001 Jan 22 |
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| Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5. | 2001 Jan 22 |
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| Direct inhibition of the hexose transporter GLUT1 by tyrosine kinase inhibitors. | 2001 Jan 23 |
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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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| B-ring substituted 5,7-dihydroxyflavonols with high-affinity binding to P-glycoprotein responsible for cell multidrug resistance. | 2001 Jan 8 |
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| Serum-dependent perinuclear accumulation of Cdc42 in mammalian cells. | 2001 Jan-Feb |
|
| Noni plant may help TB. | 2001 Mar |
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| Presence of aldose reductase inhibitors in tea leaves. | 2001 Mar |
|
| Flavonoids and phenylpropanoid derivatives from Campanula barbata. | 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 |
|
| 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 |
|
| Quercetin inhibits the expression and function of the androgen receptor in LNCaP prostate cancer cells. | 2001 Mar |
|
| Biochemical characterization of galloyl pedunculagin (ellagitannin) as a selective inhibitor of the beta-regulatory subunit of A-kinase in vitro. | 2001 Mar |
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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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| PI3K inhibitors reverse the suppressive actions of insulin on CYP2E1 expression by activating stress-response pathways in primary rat hepatocytes. | 2001 May |
|
| 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
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
| Substance Class |
Chemical
Created
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on
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Thu Jul 06 10:41:03 UTC 2023
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| Record UNII |
9IKM0I5T1E
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| Record Status |
Validated (UNII)
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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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C792
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QUERCETIN
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9060
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3529
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C401828
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DB04216
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57694
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
In vitro hydroxyl radical scavenging assay(Hydroxy Radical) IC50 expressed as ug/mL = 0.31 +/- 0.02.
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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TRANSPORTER -> INHIBITOR | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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TRANSPORTER -> INHIBITOR |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SOLVATE->ANHYDROUS | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
The compound was screened for it's antioxidant capacity in the DPPH assay, and displayed a high antioxidant activity, with an IC50 value of 39.7 uM.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ORAC value expressed as umol TE/g for this compound was 12,300 +/- 1070.
ORAC is a chemical antioxidant assay that is based on the inhibition of the peroxyl-radical induced oxidation initiated by thermal decomposition of AAPH. CAP-e value expressed as GAE/g was 5510 +/- 443.
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METABOLITE -> PARENT |
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PRODRUG -> METABOLITE ACTIVE |
To overcome these limitations, QC12, a water-soluble glycine carbamate prodrug of quercetin, was synthesized and evaluated in a clinical study to investigate its pharmacokinetics following oral administrations to cancer patients.
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IMPURITY -> PARENT |
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ACTIVE MOIETY |