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 |
|---|---|---|
| Effects of daily oral administration of quercetin chalcone and modified citrus pectin on implanted colon-25 tumor growth in Balb-c mice. | 2000 Dec |
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| Suppression by flavonoids of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells: structure-activity relationship. | 2000 Jul |
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| Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines. | 2000 Jul-Aug |
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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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| Suppression of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells by chemopreventive agents with a resorcin-type structure. | 2000 May |
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| Spontaneous shift in transcriptional profile of explanted glomeruli via activation of the MAP kinase family. | 2000 Nov |
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| Differential estrogen receptor binding of estrogenic substances: a species comparison. | 2000 Nov 15 |
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| Synergy between ethanol and grape polyphenols, quercetin, and resveratrol, in the inhibition of the inducible nitric oxide synthase pathway. | 2000 Nov 15 |
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| Anti-apoptotic effect of quercetin: intervention in the JNK- and ERK-mediated apoptotic pathways. | 2000 Sep |
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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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| 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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| 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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| 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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| Identification of quercetin glucuronides in human plasma by high-performance liquid chromatography-tandem mass spectrometry. | 2001 Apr 5 |
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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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| Reduction of dehydroascorbic acid by homocysteine. | 2001 Feb 16 |
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| The neuroprotective effects of phytoestrogens on amyloid beta protein-induced toxicity are mediated by abrogating the activation of caspase cascade in rat cortical neurons. | 2001 Feb 16 |
|
| 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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| 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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| 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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| Interaction of quercetin glucosides with the intestinal sodium/glucose co-transporter (SGLT-1). | 2001 Jan 26 |
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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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| Serum-dependent perinuclear accumulation of Cdc42 in mammalian cells. | 2001 Jan-Feb |
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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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| Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. | 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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| 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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| 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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| 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 |
|
| 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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| 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 |
|
| 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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| 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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M9420
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SUB15072MIG
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341
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9219
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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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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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TRANSPORTER -> INHIBITOR |
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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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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 |
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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