Page last updated: 2024-11-10

resveratrol-4'-o-glucuronide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

resveratrol-4'-O-glucuronide: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5273284
CHEMBL ID3526962
CHEBI ID175992
MeSH IDM0483531

Synonyms (20)

Synonym
trans-resveratrol 4'-o-glucuronide
(2s,3s,4s,5r,6s)-6-[4-[(e)-2-(3,5-dihydroxyphenyl)ethenyl]phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
CHEBI:175992
(2s,3s,4s,5r,6s)-6-[4-[(e)-2-(3,5-dihydroxyphenyl)vinyl]phenoxy]-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
resveratrol metabolite 1
.beta.-d-glucopyranosiduronic acid, 4-[(e)-2-(3,5-dihydroxyphenyl)ethenyl]phenyl
resveratrol-4'-o-glucuronide
387372-20-5
CHEMBL3526962
(2s,3s,4s,5r,6s)-6-{4-[(e)-2-(3,5-dihydroxyphenyl)ethenyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
4-[2-(3,5-dihydroxyphenyl)ethenyl]phenyl hexopyranosiduronic acid
DTXSID80693974
Q27464846
trans resveratrol 4o-b-d-glucuronide
AS-6001
resveratrol-4'-o-d-glucuronide
AKOS037645302
trans-resveratrol 4'-o--d-glucopyranoside
trans-resveratrol 4'-o-?-d-glucuronide
trans-resveratrol-4'-o-d-glucuronide

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Synthesis of RES conjugates and development and validation of a sensitive bioanalytical assay were applied to pharmacokinetic evaluation of RES and its circulating monoconjugates in C57BL mice."( Analytical method development for synthesized conjugated metabolites of trans-resveratrol, and application to pharmacokinetic studies.
Canney, DJ; Iwuchukwu, OF; Nagar, S; Sharan, S, 2012
)
0.38
" A cellular pharmacokinetic model integrating resveratrol transport/metabolism with glucuronide hydrolysis/excretion was well fitted to the experimental data, allowing derivation of the efflux rate constant values in the absence or presence of shRNA targeting MRP4."( Efflux Transport Characterization of Resveratrol Glucuronides in UDP-Glucuronosyltransferase 1A1 Transfected HeLa Cells: Application of a Cellular Pharmacokinetic Model to Decipher the Contribution of Multidrug Resistance-Associated Protein 4.
Dong, D; Li, F; Quan, E; Wang, S; Wu, B, 2016
)
0.43

Bioavailability

ExcerptReferenceRelevance
"Trans-3,5,4'-trihydroxystilbene (trans-resveratrol, RES) exhibits very low bioavailability due to extensive conjugative metabolism."( Analytical method development for synthesized conjugated metabolites of trans-resveratrol, and application to pharmacokinetic studies.
Canney, DJ; Iwuchukwu, OF; Nagar, S; Sharan, S, 2012
)
0.38
"Due to the low bioavailability of resveratrol, determining whether its metabolites exert any beneficial effect is an interesting issue."( Delipidating effect of resveratrol metabolites in 3T3-L1 adipocytes.
Andrés-Lacueva, C; Churruca, I; Eseberri, I; Lasa, A; Portillo, MP, 2012
)
0.38
"Altogether, our data provide significant new insight into the molecular mechanism of RSV and support the notion that despite low bioavailability in vivo, RSV biological effects could be mediated by its metabolites."( Resveratrol metabolites inhibit human metastatic colon cancer cells progression and synergize with chemotherapeutic drugs to induce cell death.
Aires, V; Cotte, AK; Delmas, D; Ghiringhelli, F; Latruffe, N; Limagne, E, 2013
)
0.39
" Its bioavailability is low and raises the possibility that the metabolites of resveratrol have biological effects."( Resveratrol 3-O-D-glucuronide and resveratrol 4'-O-D-glucuronide inhibit colon cancer cell growth: evidence for a role of A3 adenosine receptors, cyclin D1 depletion, and G1 cell cycle arrest.
Carew, MA; Carrington, S; Meira, LB; Modjtahedi, H; Polycarpou, E; Tyrrell, E, 2013
)
0.39
"Due to the low bioavailability of resveratrol, determining whether its metabolites exert any beneficial effect is an interesting issue."( Resveratrol metabolites modify adipokine expression and secretion in 3T3-L1 pre-adipocytes and mature adipocytes.
Churruca, I; Eseberri, I; Lasa, A; Portillo, MP, 2013
)
0.39
" Indeed, several studies have implicated this bioavailability trait as a major road-block to resveratrol's potential clinical applications."( Toward Resolving the Resveratrol Conundrum: Synthesis and
Adsool, VA; Cui, YT; Goh, YL; Pendharkar, V, 2017
)
0.46
" TRG had poor absolute bioavailability in rats."( Pharmacokinetics, tissue distribution and excretion study of trans-resveratrol-3-O-glucoside and its two metabolites in rats.
Dong, C; Su, M; Wan, J; Zhou, M, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
glycosideA glycosyl compound resulting from the attachment of a glycosyl group to a non-acyl group RO-, RS-, RSe-, etc. The bond between the glycosyl group and the non-acyl group is called a glycosidic bond. By extension, the terms N-glycosides and C-glycosides are used as class names for glycosylamines and for compounds having a glycosyl group attached to a hydrocarbyl group respectively. These terms are misnomers and should not be used. The preferred terms are glycosylamines and C-glycosyl compounds, respectively.
stilbenoidAny olefinic compound characterised by a 1,2-diphenylethylene backbone.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID1430694Drug level in human hepatocytes treated with resveratrol at 5 uM by LC-MS/MS analysis2017ACS medicinal chemistry letters, May-11, Volume: 8, Issue:5
Toward Resolving the Resveratrol Conundrum: Synthesis and
AID1884061Antibacterial activity against Staphylococcus aureus LMG 10147 incubated for 20 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1884068Antibacterial activity against Clostridium tetani CECT 4629 incubated for 24 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1884066Antibacterial activity against Clostridium-ihumii AP5 incubated for 24 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1884062Antibacterial activity against Staphylococcus aureus LMG 15975 incubated for 20 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1220757AUC (0 to t) in C57BL/6 mouse treated with 5 mg/kg of resveratrol-3-glucuronide administered intraarterially by LC-MS/MS analysis2012Drug metabolism and disposition: the biological fate of chemicals, Oct, Volume: 40, Issue:10
In vivo-formed versus preformed metabolite kinetics of trans-resveratrol-3-sulfate and trans-resveratrol-3-glucuronide.
AID1884053Antibacterial activity against Bacillus cereus ATCC 14579 incubated for 20 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1220768AUC (0 to infinity) in C57BL/6 mouse treated with 15 mg/kg of trans-3,5,4'-Trihydroxystilbene [trans-resveratrol] administered intraarterially by LC-MS/MS analysis2012Drug metabolism and disposition: the biological fate of chemicals, Oct, Volume: 40, Issue:10
In vivo-formed versus preformed metabolite kinetics of trans-resveratrol-3-sulfate and trans-resveratrol-3-glucuronide.
AID1884056Antibacterial activity against Enterococcus faecalis LMG 16216 incubated for 20 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1884067Antibacterial activity against Clostridium perfringens CECT376 incubated for 24 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1884059Antibacterial activity against Enterococcus faecalis LMG 16003 incubated for 20 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1220758AUC (0 to infinity) in C57BL/6 mouse treated with 5 mg/kg of resveratrol-3-glucuronide administered intraarterially by LC-MS/MS analysis2012Drug metabolism and disposition: the biological fate of chemicals, Oct, Volume: 40, Issue:10
In vivo-formed versus preformed metabolite kinetics of trans-resveratrol-3-sulfate and trans-resveratrol-3-glucuronide.
AID1884069Antimicrobial activity against Escherichia coli LMG 8224 incubated for 20 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1884060Antibacterial activity against Staphylococcus aureus LMG 8224 incubated for 20 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1884054Antibacterial activity against Bacillus cereus ATCC 10987 incubated for 20 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1884065Antibacterial activity against Clostridium difficile CECT531 incubated for 24 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1220767AUC (0 to t) in C57BL/6 mouse treated with 15 mg/kg of trans-3,5,4'-Trihydroxystilbene [trans-resveratrol] administered intraarterially by LC-MS/MS analysis2012Drug metabolism and disposition: the biological fate of chemicals, Oct, Volume: 40, Issue:10
In vivo-formed versus preformed metabolite kinetics of trans-resveratrol-3-sulfate and trans-resveratrol-3-glucuronide.
AID1884063Antibacterial activity against Clostridium beijerinckii B504 incubated for 24 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1884055Antibacterial activity against Enterococcus faecalis LMG 08222 incubated for 20 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1884057Antibacterial activity against Enterococcus faecalis V583 incubated for 20 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1220759Terminal half life in C57BL/6 mouse treated with 5 mg/kg of resveratrol-3-glucuronide administered intraarterially by LC-MS/MS analysis2012Drug metabolism and disposition: the biological fate of chemicals, Oct, Volume: 40, Issue:10
In vivo-formed versus preformed metabolite kinetics of trans-resveratrol-3-sulfate and trans-resveratrol-3-glucuronide.
AID1220769Terminal half life in C57BL/6 mouse treated with 15 mg/kg of trans-3,5,4'-Trihydroxystilbene [trans-resveratrol] administered intraarterially by LC-MS/MS analysis2012Drug metabolism and disposition: the biological fate of chemicals, Oct, Volume: 40, Issue:10
In vivo-formed versus preformed metabolite kinetics of trans-resveratrol-3-sulfate and trans-resveratrol-3-glucuronide.
AID1884058Antibacterial activity against Enterococcus faecalis LMG 11423 incubated for 20 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
AID1884064Antibacterial activity against Clostridium botulinum CECT551 incubated for 24 hrs by CLSI based broth microdilution method2022Journal of natural products, 06-24, Volume: 85, Issue:6
Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (7.69)29.6817
2010's22 (84.62)24.3611
2020's2 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.89

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.89 (24.57)
Research Supply Index3.33 (2.92)
Research Growth Index5.23 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.89)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (3.85%)5.53%
Reviews1 (3.85%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (92.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]