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.
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 |
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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 |
||
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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Heat-shock protein-73 protects against small intestinal warm ischemia-reperfusion injury in the rat. | 1999 Apr |
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Effects of the wine polyphenolics quercetin and resveratrol on pro-inflammatory cytokine expression in RAW 264.7 macrophages. | 1999 Apr 15 |
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A search for anti-viral properties in Panamanian medicinal plants. The effects on HIV and its essential enzymes. | 1999 Jan |
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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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Expression of antioxidant proteins in human intestinal Caco-2 cells treated with dietary flavonoids. | 1999 Nov 15 |
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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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Effects of luteolin, quercetin and baicalein on immunoglobulin E-mediated mediator release from human cultured mast cells. | 2000 Apr |
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Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines. | 2000 Jul-Aug |
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The effect of mycophenolate mofetil and polyphenolic bioflavonoids on renal ischemia reperfusion injury and repair. | 2000 Mar |
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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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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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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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A malonylated anthocyanin and flavonols in blue Meconopsis flowers. | 2001 Feb |
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The etiologies, pathophysiology, and alternative/complementary treatment of asthma. | 2001 Feb |
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Reduction of dehydroascorbic acid by homocysteine. | 2001 Feb 16 |
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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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LC coupled to ion-trap MS for the rapid screening and detection of polyphenol antioxidants from Helichrysum stoechas. | 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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Luteolin inhibits an endotoxin-stimulated phosphorylation cascade and proinflammatory cytokine production in macrophages. | 2001 Jan |
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Synthesis, characterization, antioxidative and antitumor activities of solid quercetin rare earth(III) complexes. | 2001 Jan 1 |
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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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Mut-Test to detect substances suppressing spontaneous mutation due to oxidative damage. | 2001 Jan 25 |
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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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Chemoprotective potentials of homoisoflavonoids and chalcones of Dracaena cinnabari: modulations of drug-metabolizing enzymes and antioxidant activity. | 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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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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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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Effects of structurally related flavonoids on cell cycle progression of human melanoma cells: regulation of cyclin-dependent kinases CDK2 and CDK1. | 2001 May 15 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 04:51:05 GMT 2023
by
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on
Sat Dec 16 04:51:05 GMT 2023
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Record UNII |
9IKM0I5T1E
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Record Status |
Validated (UNII)
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Record Version |
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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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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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Related Record | Type | Details | ||
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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 |
Related Record | Type | Details | ||
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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 |