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Details

Stereochemistry ACHIRAL
Molecular Formula C15H10O7
Molecular Weight 302.2363
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUERCETIN

SMILES

c1cc(c(cc1-c2c(c(=O)c3c(cc(cc3o2)O)O)O)O)O

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

HIDE SMILES / InChI

Molecular Formula C15H10O7
Molecular Weight 302.2363
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

Curator's Comment:: There is limited ability of the reviewed flavonoids to access the brain

Originator

Curator's Comment:: Bioflavonoids were first discovered by Nobel Prize laureate Albert Szent Gyorgyi in the year 1930.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
500 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
2077 μg × min/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
47 min
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

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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/)
potent [IC50 0.65 uM]
yes [IC50 15.9 uM]
weak (co-administration study)
Comment: AUC increase of 24%, Cmax increase of 31%
yes [IC50 4.22 uM]
yes (co-administration study)
Comment: 1.8-fold increase in AUC8h and 1.5 fold increase in Cmax
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
yes
weak (co-administration study)
Comment: decreased enzyme activity by 10.4%
Page: 5.0
yes
weak (co-administration study)
Comment: increased enzyme activity by 25.3%
Page: 1.0
Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Modulation of apoptotic and inflammatory genes by bioflavonoids and angiotensin II inhibition in ureteral obstruction.
2000 Aug 1
Effects of daily oral administration of quercetin chalcone and modified citrus pectin on implanted colon-25 tumor growth in Balb-c mice.
2000 Dec
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.
2000 Jul-Aug
The effect of mycophenolate mofetil and polyphenolic bioflavonoids on renal ischemia reperfusion injury and repair.
2000 Mar
Differential estrogen receptor binding of estrogenic substances: a species comparison.
2000 Nov 15
Influence of quercetin on B16 melanotic melanoma growth in C57BL/6 mice and on activity of some acid hydrolases in melanoma tissue.
2001
Protective effect of phenolic compounds isolated from the hooks and stems of Uncaria sinensis on glutamate-induced neuronal death.
2001
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
Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus.
2001 Apr
Constituents of Afzelia bella stem bark.
2001 Apr
Kaempferide triglycoside: a possible factor of resistance of carnation (Dianthus caryophyllus) to Fusarium oxysporum f. sp. dianthi.
2001 Apr
Evaluation of polyphenolic and flavonoid compounds in honeybee-collected pollen produced in Spain.
2001 Apr
Measurement of copper-binding sites on low density lipoprotein.
2001 Apr
Natural therapies for ocular disorders, part two: cataracts and glaucoma.
2001 Apr
Identification of quercetin glucuronides in human plasma by high-performance liquid chromatography-tandem mass spectrometry.
2001 Apr 5
Pre-clinical and clinical study of QC12, a water-soluble, pro-drug of quercetin.
2001 Feb
Guaiane dimers from Xylopia vielana.
2001 Feb
Polyphyenolics increase t-PA and u-PA gene transcription in cultured human endothelial cells.
2001 Feb
Reduction of dehydroascorbic acid by homocysteine.
2001 Feb 16
Induction of human NAD(P)H:quinone oxidoreductase (NQO1) gene expression by the flavonol quercetin.
2001 Feb 3
[Polyphenol compounds from Hamamelis virginiana L].
2001 Jan
Polyphenolic compounds from Geranium pratense and their free radical scavenging activities.
2001 Jan
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
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
Luteolin inhibits an endotoxin-stimulated phosphorylation cascade and proinflammatory cytokine production in macrophages.
2001 Jan
Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids in macrophage J774A.1.
2001 Jan 12
Searching for the physiological function of 17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: studies of substrate specificity and expression analysis.
2001 Jan 22
Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.
2001 Jan 22
Interaction of quercetin glucosides with the intestinal sodium/glucose co-transporter (SGLT-1).
2001 Jan 26
Characterization of enzymes participating in carbonyl reduction of 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in human placenta.
2001 Jan 30
Interaction of sheep liver cytosolic aldehyde dehydrogenase with quercetin, resveratrol and diethylstilbestrol.
2001 Jan 30
B-ring substituted 5,7-dihydroxyflavonols with high-affinity binding to P-glycoprotein responsible for cell multidrug resistance.
2001 Jan 8
Noni plant may help TB.
2001 Mar
Presence of aldose reductase inhibitors in tea leaves.
2001 Mar
Enhanced antioxidant activity after chlorination of quercetin by hypochlorous acid.
2001 Mar
Flavonoids and phenylpropanoid derivatives from Campanula barbata.
2001 Mar
Treatment of interstitial cystitis with a quercetin supplement.
2001 Mar
Flavonoid characters contributing to the taxonomic revision of the Hebe parviflora complex.
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
Simultaneous determination of quercetin, kaempferol and (E)-cinnamic acid in vegetative organs of Schisandra chinensis Baill. by HPLC.
2001 Mar
Protective effect of various antioxidants on the toxicity of sulphur mustard administered to mice by inhalation or percutaneous routes.
2001 Mar 14
Antihypertensive effects of the flavonoid quercetin in spontaneously hypertensive rats.
2001 May
Fast repair of the radical cations of dCMP and poly C by quercetin and rutin.
2001 May
Induction of stress response proteins and experimental renal ischemia/reperfusion.
2001 May
Influence of prenylated and non-prenylated flavonoids on liver microsomal lipid peroxidation and oxidative injury in rat hepatocytes.
2001 May
Modulation of multidrug resistance protein 1 (MRP1/ABCC1) transport and atpase activities by interaction with dietary flavonoids.
2001 May
PI3K inhibitors reverse the suppressive actions of insulin on CYP2E1 expression by activating stress-response pathways in primary rat hepatocytes.
2001 May
Structural damage to proteins caused by free radicals: asessment, protection by antioxidants, and influence of protein binding.
2001 May 15
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
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 Fri Jun 25 21:45:12 UTC 2021
Edited
by admin
on Fri Jun 25 21:45:12 UTC 2021
Record UNII
9IKM0I5T1E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUERCETIN
DSC   HSDB   INCI   MI   VANDF   WHO-DD  
INCI  
Official Name English
FLAVONE, 3,3',4',5,7-PENTAHYDROXY-
Common Name English
3'-HYDROXYKAEMPFEROL
Common Name English
LDN-0052529
Code English
3,3',4',5,7-PENTAHYDROXYFLAVONE
Systematic Name English
KORVITIN
Brand Name English
QUERCETIN (CONSTITUENT OF HAWTHORN LEAF WITH FLOWER) [DSC]
Common Name English
QUERCETIN (CONSTITUENT OF GINKGO) [DSC]
Common Name English
QUERCETIN [WHO-DD]
Common Name English
MELETIN
Common Name English
QUERTINE
Common Name English
2-(3,4-DIHYDROXYPHENYL)-3,5,7-TRIHYDROXY-4H-BENZOPYRAN-4-ONE
Systematic Name English
4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-3,5,7-TRIHYDROXY-
Systematic Name English
QUERCETIN [INCI]
Common Name English
CYANIDELONON 1522
Systematic Name English
LIPOFLAVON
Common Name English
QUERCETINE
Common Name English
FLAVONE, 3,4',5,5',7-PENTAHYDROXY-
Systematic Name English
QUERCETIN [IARC]
Common Name English
2-(3,4-DIHYDROXYPHENYL)-3,5,7-TRIHYDROXY-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
SOPHORETIN
Common Name English
C.I. 75670
Common Name English
CI-75670
Common Name English
XANTHAURINE
Common Name English
QUERTIN
Common Name English
3,5,7-TRIHYDROXY-2-(3,4-DIHYDROXYPHENYL)-4H-CHROMEN-4-ONE
Systematic Name English
CORVITIN
Brand Name English
QUERCETIN [HSDB]
Common Name English
QUERCETOL
Common Name English
NSC-9219
Code English
QUERCETIN [USP-RS]
Common Name English
3,5,7,3',4'-PENTAHYDROXYFLAVONE
Systematic Name English
QUERCETIN [VANDF]
Common Name English
QUERCETIN [MI]
Common Name English
QUERCETIN [DSC]
Common Name English
NSC-57655
Code English
CYANIDENOLON 1522
Brand Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 664018
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
DSLD 1099 (Number of products:1551)
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
LIVERTOX 822
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
Code System Code Type Description
DRUG CENTRAL
3514
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
PRIMARY
EPA CompTox
117-39-5
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
PRIMARY
MESH
D011794
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
PRIMARY
MERCK INDEX
M9420
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
PRIMARY Merck Index
EVMPD
SUB15072MIG
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-187-1
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
PRIMARY
PUBCHEM
5280343
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
PRIMARY
USP_CATALOG
1592409
Created by admin on Fri Jun 25 21:45:13 UTC 2021 , Edited by admin on Fri Jun 25 21:45:13 UTC 2021
PRIMARY USP-RS
NCI_THESAURUS
C792
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
PRIMARY
WIKIPEDIA
QUERCETIN
Created by admin on Fri Jun 25 21:45:13 UTC 2021 , Edited by admin on Fri Jun 25 21:45:13 UTC 2021
PRIMARY
FDA UNII
9IKM0I5T1E
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
PRIMARY
CAS
117-39-5
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
PRIMARY
RXCUI
9060
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
PRIMARY RxNorm
HSDB
3529
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
PRIMARY
MESH
C401828
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
PRIMARY
DRUG BANK
DB04216
Created by admin on Fri Jun 25 21:45:12 UTC 2021 , Edited by admin on Fri Jun 25 21:45:12 UTC 2021
PRIMARY
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In vitro hydroxyl radical scavenging assay(Hydroxy Radical) IC50 expressed as ug/mL = 0.31 +/- 0.02.
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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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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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