Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H18O13 |
| Molecular Weight | 478.3598 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@H]1OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C4=CC=C(O)C(O)=C4)C(O)=O
InChI
InChIKey=DUBCCGAQYVUYEU-ZUGPOPFOSA-N
InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1
| Molecular Formula | C21H18O13 |
| Molecular Weight | 478.3598 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Modulation of flavonoid biosynthetic pathway genes and anthocyanins due to virus infection in grapevine (Vitis vinifera L.) leaves. | 2010-08-23 |
|
| Chemical constituents of Asparagus. | 2010-07 |
|
| Changes of metabolic profiles in urine after oral administration of quercetin in rats. | 2010-06 |
|
| Platelet-mediated metabolism of the common dietary flavonoid, quercetin. | 2010-03-12 |
|
| A structural basis for the inhibition of collagen-stimulated platelet function by quercetin and structurally related flavonoids. | 2010-03 |
|
| Ultra-performance liquid chromatography-tandem mass spectrometry analysis of the bioactive components and their metabolites of Shaofu Zhuyu decoction active extract in rat plasma. | 2010-02-01 |
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| Deconjugation kinetics of glucuronidated phase II flavonoid metabolites by beta-glucuronidase from neutrophils. | 2010 |
|
| Quercetin metabolites and protection against peroxynitrite-induced oxidative hepatic injury in rats. | 2009-10 |
|
| Effect of quercetin on paraoxonase 2 levels in RAW264.7 macrophages and in human monocytes--role of quercetin metabolism. | 2009-09-23 |
|
| Antioxidative effect and active components from leaves of Lotus ( Nelumbo nucifera ). | 2009-08-12 |
|
| [HPLC-MS analysis of quercetin and its metabolites in portal vein after intragastrical administration of quercetin in rats]. | 2009-07 |
|
| Glucuronidated and sulfated metabolites of the flavonoid quercetin prevent endothelial dysfunction but lack direct vasorelaxant effects in rat aorta. | 2009-05 |
|
| Quercetin glucuronide inhibits cell migration and proliferation by platelet-derived growth factor in vascular smooth muscle cells. | 2009-02 |
|
| Immunochemical detection of flavonoid glycosides: development, specificity, and application of novel monoclonal antibodies. | 2008-08-15 |
|
| [Study on aqueous chemical constituents from the flower buds of Eugenia caryophylla]. | 2008-07 |
|
| Flavanol and flavonol contents of cocoa powder products: influence of the manufacturing process. | 2008-05-14 |
|
| Spermidine and flavonoid conjugates from peanut (Arachis hypogaea) flowers. | 2008-05-14 |
|
| Macrophage as a target of quercetin glucuronides in human atherosclerotic arteries: implication in the anti-atherosclerotic mechanism of dietary flavonoids. | 2008-04-04 |
|
| Metabolic transformation has a profound effect on anti-inflammatory activity of flavonoids such as quercetin: lack of association between antioxidant and lipoxygenase inhibitory activity. | 2008-03-01 |
|
| High-performance thin-layer chromatography method for quantitative determination of oenothein B and quercetin glucuronide in aqueous extract of Epilobii angustifolii herba. | 2007-11-30 |
|
| Biosafety, antioxidant status, and metabolites in urine after consumption of dried cranberry juice in healthy women: a pilot double-blind placebo-controlled trial. | 2007-04-18 |
|
| Radical scavenging activity and composition of raspberry (Rubus idaeus) leaves from different locations in Lithuania. | 2007-02 |
|
| The relative contribution of the small and large intestine to the absorption and metabolism of rutin in man. | 2006-10 |
|
| Absorption, excretion and metabolite profiling of methyl-, glucuronyl-, glucosyl- and sulpho-conjugates of quercetin in human plasma and urine after ingestion of onions. | 2006-07 |
|
| Divergent effects of quercetin conjugates on angiogenesis. | 2006-05 |
|
| Red wine alcohol promotes quercetin absorption and directs its metabolism towards isorhamnetin and tamarixetin in rat intestine in vitro. | 2006-04 |
|
| Effect of Epilobium angustifolium L. extracts and polyphenols on cell proliferation and neutral endopeptidase activity in selected cell lines. | 2006-01 |
|
| Heterologous expression of active human uridine diphosphate glucuronosyltransferase 1A3 in Chinese hamster lung cells. | 2005-01-07 |
|
| Flavonoid metabolites in human plasma and urine after the consumption of red onions: analysis by liquid chromatography with photodiode array and full scan tandem mass spectrometric detection. | 2004-11-26 |
|
| Characterisation of metabolites of the putative cancer chemopreventive agent quercetin and their effect on cyclo-oxygenase activity. | 2004-09-13 |
|
| Properties of quercetin conjugates: modulation of LDL oxidation and binding to human serum albumin. | 2004-08 |
|
| Bioguided isolation and identification of the nonvolatile antioxidant compounds from fennel (Foeniculum vulgare Mill.) waste. | 2004-04-07 |
|
| Effect of quercetin conjugates on vascular permeability and expression of adhesion molecules. | 2004 |
|
| Constituents of Hypericum laricifolium and their cyclooxygenase (COX) enzyme activities. | 2003-12 |
|
| Intracellular metabolism and bioactivity of quercetin and its in vivo metabolites. | 2003-05-15 |
|
| Metabolism of quercetin-7- and quercetin-3-glucuronides by an in vitro hepatic model: the role of human beta-glucuronidase, sulfotransferase, catechol-O-methyltransferase and multi-resistant protein 2 (MRP2) in flavonoid metabolism. | 2003-02-01 |
|
| Quercetin glucuronide prevents VSMC hypertrophy by angiotensin II via the inhibition of JNK and AP-1 signaling pathway. | 2002-05-24 |
|
| Superoxide scavenging by polyphenols: effect of conjugation and dimerization. | 2002 |
|
| Human metabolism of dietary flavonoids: identification of plasma metabolites of quercetin. | 2001-12 |
|
| Identification and determination of glucuronides and their aglycones in Erigeron breviscapus by liquid chromatography-tandem mass spectrometry. | 2001-09-14 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 20:19:22 GMT 2025
by
admin
on
Wed Apr 02 20:19:22 GMT 2025
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| Record UNII |
RY36PD0CQ2
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| Record Status |
Validated (UNII)
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| Record Version |
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RY36PD0CQ2
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Miquelianin
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5274585
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DTXSID70945358
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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 44.4 uM.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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PARENT -> METABOLITE |
