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 |
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| 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 |
|---|---|---|
| Heat-shock protein-73 protects against small intestinal warm ischemia-reperfusion injury in the rat. | 1999 Apr |
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| Increased antiviral activity of cyclic urea HIV protease inhibitors by modifying the P1/P1' substituents. | 1999 Aug 2 |
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| Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially. | 1999 Jun 15 |
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| Modulation of apoptotic and inflammatory genes by bioflavonoids and angiotensin II inhibition in ureteral obstruction. | 2000 Aug 1 |
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| Quercetin inhibits p21-RAS expression in human colon cancer cell lines and in primary colorectal tumors. | 2000 Feb 1 |
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| Oxidative stress involvement in chemically induced differentiation of K562 cells. | 2000 Jan 1 |
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| Differential effects of flavonoid compounds on tumor promoter-induced activation of the human CYP1A2 enhancer. | 2000 Jan 1 |
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| Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines. | 2000 Jul-Aug |
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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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| Protective effect of phenolic compounds isolated from the hooks and stems of Uncaria sinensis on glutamate-induced neuronal death. | 2001 |
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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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| Ca2+-induced contraction of cat esophageal circular smooth muscle cells. | 2001 Apr |
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| Guaiane dimers from Xylopia vielana. | 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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| Separation of kaempferols in Impatients balsamina flowers by capillary electrophoresis with electrochemical detection. | 2001 Feb 16 |
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| Phenolic constituents of Phenax angustifolius. | 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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| Mut-Test to detect substances suppressing spontaneous mutation due to oxidative damage. | 2001 Jan 25 |
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| Interaction of quercetin glucosides with the intestinal sodium/glucose co-transporter (SGLT-1). | 2001 Jan 26 |
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| Flavonoid characters contributing to the taxonomic revision of the Hebe parviflora complex. | 2001 Mar |
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| 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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| Determination of phenolic acids and flavonoids of apple and pear by high-performance liquid chromatography. | 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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| Influence of prenylated and non-prenylated flavonoids on liver microsomal lipid peroxidation and oxidative injury in rat hepatocytes. | 2001 May |
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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
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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100000079143
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m9420
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SUB15072MIG
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204-187-1
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C792
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QUERCETIN
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3529
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C401828
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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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TRANSPORTER -> INHIBITOR |
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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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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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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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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 |
USP
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PARENT -> IMPURITY |
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ACTIVE MOIETY |