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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
Structure of QUERCITURONE

SMILES

O[C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@H]1OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C4=CC(O)=C(O)C=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

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
Identification and determination of glucuronides and their aglycones in Erigeron breviscapus by liquid chromatography-tandem mass spectrometry.
2001 Sep 14
Superoxide scavenging by polyphenols: effect of conjugation and dimerization.
2002
Quercetin glucuronide prevents VSMC hypertrophy by angiotensin II via the inhibition of JNK and AP-1 signaling pathway.
2002 May 24
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 Feb 1
Intracellular metabolism and bioactivity of quercetin and its in vivo metabolites.
2003 May 15
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 Nov 26
Characterisation of metabolites of the putative cancer chemopreventive agent quercetin and their effect on cyclo-oxygenase activity.
2004 Sep 13
Red wine alcohol promotes quercetin absorption and directs its metabolism towards isorhamnetin and tamarixetin in rat intestine in vitro.
2006 Apr
Effect of Epilobium angustifolium L. extracts and polyphenols on cell proliferation and neutral endopeptidase activity in selected cell lines.
2006 Jan
Absorption, excretion and metabolite profiling of methyl-, glucuronyl-, glucosyl- and sulpho-conjugates of quercetin in human plasma and urine after ingestion of onions.
2006 Jul
Divergent effects of quercetin conjugates on angiogenesis.
2006 May
The relative contribution of the small and large intestine to the absorption and metabolism of rutin in man.
2006 Oct
Biosafety, antioxidant status, and metabolites in urine after consumption of dried cranberry juice in healthy women: a pilot double-blind placebo-controlled trial.
2007 Apr 18
Radical scavenging activity and composition of raspberry (Rubus idaeus) leaves from different locations in Lithuania.
2007 Feb
High-performance thin-layer chromatography method for quantitative determination of oenothein B and quercetin glucuronide in aqueous extract of Epilobii angustifolii herba.
2007 Nov 30
Macrophage as a target of quercetin glucuronides in human atherosclerotic arteries: implication in the anti-atherosclerotic mechanism of dietary flavonoids.
2008 Apr 4
Immunochemical detection of flavonoid glycosides: development, specificity, and application of novel monoclonal antibodies.
2008 Aug 15
[Study on aqueous chemical constituents from the flower buds of Eugenia caryophylla].
2008 Jul
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 Mar 1
Flavanol and flavonol contents of cocoa powder products: influence of the manufacturing process.
2008 May 14
Spermidine and flavonoid conjugates from peanut (Arachis hypogaea) flowers.
2008 May 14
Antioxidative effect and active components from leaves of Lotus ( Nelumbo nucifera ).
2009 Aug 12
Quercetin glucuronide inhibits cell migration and proliferation by platelet-derived growth factor in vascular smooth muscle cells.
2009 Feb
[HPLC-MS analysis of quercetin and its metabolites in portal vein after intragastrical administration of quercetin in rats].
2009 Jul
Glucuronidated and sulfated metabolites of the flavonoid quercetin prevent endothelial dysfunction but lack direct vasorelaxant effects in rat aorta.
2009 May
Quercetin metabolites and protection against peroxynitrite-induced oxidative hepatic injury in rats.
2009 Oct
Effect of quercetin on paraoxonase 2 levels in RAW264.7 macrophages and in human monocytes--role of quercetin metabolism.
2009 Sep 23
Deconjugation kinetics of glucuronidated phase II flavonoid metabolites by beta-glucuronidase from neutrophils.
2010
Modulation of flavonoid biosynthetic pathway genes and anthocyanins due to virus infection in grapevine (Vitis vinifera L.) leaves.
2010 Aug 23
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 Feb 1
Chemical constituents of Asparagus.
2010 Jul
Changes of metabolic profiles in urine after oral administration of quercetin in rats.
2010 Jun
A structural basis for the inhibition of collagen-stimulated platelet function by quercetin and structurally related flavonoids.
2010 Mar
Platelet-mediated metabolism of the common dietary flavonoid, quercetin.
2010 Mar 12
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 22:03:23 GMT 2023
Edited
by admin
on Fri Dec 15 22:03:23 GMT 2023
Record UNII
RY36PD0CQ2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUERCITURONE
Common Name English
QUERCETIN 3-O-.BETA.-D-GLUCURONOPYRANOSIDE
Common Name English
QUERCETIN .BETA.-GLUCURONIDE
Common Name English
GLUCOPYRANOSIDURONIC ACID, 2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4-OXO-4H-1-BENZOPYRAN-3-YL, .BETA.-D-
Common Name English
QUERCETIN GLUCURONIDE
Common Name English
QUERCETIN 3-.BETA.-GLUCURONIDE
Common Name English
QUERCETIN-3-GLUCOSIDURONIC ACID
Common Name English
QUERCETIN-3-.BETA.-D-GLUCURONIDE
Common Name English
QUERCITURON
Common Name English
HMDB29212
Code English
.BETA.-D-GLUCOPYRANOSIDURONIC ACID, 2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4-OXO-4H-1-BENZOPYRAN-3-YL
Common Name English
QUERCETIN 3-O-GLUCURONIDE
Common Name English
MIKWELIANIN
Common Name English
MIQUELIANIN
Common Name English
QUERCETIN-3-O-.BETA.-D-GLUCURONIDE
Common Name English
QUERCETIN 3-GLUCURONIDE
Common Name English
Code System Code Type Description
CAS
22688-79-5
Created by admin on Fri Dec 15 22:03:23 GMT 2023 , Edited by admin on Fri Dec 15 22:03:23 GMT 2023
PRIMARY
CHEBI
66395
Created by admin on Fri Dec 15 22:03:23 GMT 2023 , Edited by admin on Fri Dec 15 22:03:23 GMT 2023
PRIMARY
FDA UNII
RY36PD0CQ2
Created by admin on Fri Dec 15 22:03:23 GMT 2023 , Edited by admin on Fri Dec 15 22:03:23 GMT 2023
PRIMARY
WIKIPEDIA
Miquelianin
Created by admin on Fri Dec 15 22:03:23 GMT 2023 , Edited by admin on Fri Dec 15 22:03:23 GMT 2023
PRIMARY
PUBCHEM
5274585
Created by admin on Fri Dec 15 22:03:23 GMT 2023 , Edited by admin on Fri Dec 15 22:03:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID70945358
Created by admin on Fri Dec 15 22:03:23 GMT 2023 , Edited by admin on Fri Dec 15 22:03:23 GMT 2023
PRIMARY
Related Record Type Details
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.
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
PARENT -> METABOLITE
Quantity of quercetin-3-glucuronide in urine of six healthy human subjects 0-24hr (total) after consumption of tomato juice containing 176 micromoles of rutin; Unit: nmoles
IN-VIVO
URINE