Page last updated: 2024-12-07

4-nitrophenylglucuronide

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

Description

4-Nitrophenylglucuronide (4-NPG) is a synthetic compound used as a model substrate for the study of glucuronidation, a major detoxification pathway in the liver. 4-NPG is metabolized by the enzyme UDP-glucuronosyltransferases (UGTs) to form 4-nitrophenylglucuronide. This compound is often used to study the kinetics and mechanism of glucuronidation. Studies of 4-NPG have shown that it is an effective substrate for UGT enzymes, allowing for the investigation of factors that influence the activity of these enzymes. The research on 4-NPG contributes to understanding the metabolism of xenobiotics, including drugs, and the role of glucuronidation in detoxification. This compound is valuable in the development of new drugs and the optimization of existing medications.'

4-nitrophenyl beta-D-glucuronide : A beta-D-glucosiduronic acid having a 4-nitrophenyl substituent at the anomeric position. [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]

Cross-References

ID SourceID
PubMed CID82565
CHEMBL ID495244
CHEBI ID90146
SCHEMBL ID964789
MeSH IDM0043437

Synonyms (43)

Synonym
4-nitrophenyl beta-d-glucuronide, >=98% (tlc)
4-nitrophenyl-beta-d-glucuronide
4-nitrophenyl beta-d-glucuronide, >=99.0% (tlc)
10344-94-2
4-nitrophenyl beta-d-glucopyranosiduronic acid
N0618
4-nitrophenyl beta-d-glucuronide
4-nitrophenyl glucuronide
CHEMBL495244
chebi:90146 ,
(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-nitrophenoxy)oxane-2-carboxylic acid
60833-84-3
p-nitrophenyl beta-d-glucopyranosiduronic acid
p-nitrophenylglucuronide
para-nitrophenylglucuronide
4-nitrophenylglucuronide
einecs 233-753-0
AKOS016009961
AKOS016015686
beta-d-glucopyranosiduronic acid, 4-nitrophenyl, labeled with carbon-14
AKOS015916643
b-d-glucopyranosiduronic acid,4-nitrophenyl
SCHEMBL964789
4-nitrophenyl b-d-glucosiduronic acid
p-nitrophenyl beta-d-glucuronide
mfcd00036210
DTXSID80209670
4-nitrophenyl i(2)-d-glucuronide
4-nitrophenyl-?-d-glucuronide
Q27162353
C3G ,
(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-nitrophenoxy)tetrahydro-2h-pyran-2-carboxylic acid
QSUILVWOWLUOEU-GOVZDWNOSA-N
b-d-glucopyranosiduronic acid,4-nitrophenyl-
FS-5447
AMY41483
STL570260
4-nitrophenyl -d-glucuronide
A896456
(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-nitrophenoxy)tetrahydro-2h-pyran-2-carboxylicacid
HY-W039892
CS-0098151
p-nitrophenyl- beta -d-glucuronide
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Occurs in Manufacturing (1 Product(s))

Product Categories

Product CategoryProducts
Vitamins & Supplements1

Products

ProductBrandCategoryCompounds Matched from IngredientsDate Retrieved
Life Extension MacuGuardĀ® Ocular Support with Saffron -- 60 SoftgelsLife ExtensionVitamins & SupplementsC3G, glycerin, maltodextrin2024-11-29 10:47:42

Roles (1)

RoleDescription
chromogenic compoundColourless, endogenous or exogenous pigment precursors that may be transformed by biological mechanisms into coloured compounds. They are used in biochemical assays and in diagnosis as indicators, particularly in the form of enzyme substrates.
[role 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]

Drug Classes (2)

ClassDescription
beta-D-glucosiduronic acidA glucosiduronic acid resulting from the formal condensation of any substance with beta-D-glucuronic acid to form a glycosidic bond.
C-nitro compoundA nitro compound having the nitro group (-NO2) attached to a carbon atom.
[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]

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Canalicular multispecific organic anion transporter 1Rattus norvegicus (Norway rat)Km20.00001.50004.34206.9000AID678893
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID678893TP_TRANSPORTER: uptake in bile canalicular membrane vesicles from Wistar rat1991Biochemical and biophysical research communications, Apr-30, Volume: 176, Issue:2
ATP-dependent transport for glucuronides in canalicular plasma membrane vesicles.
AID681917TP_TRANSPORTER: inhibition of MTX uptake (MTX: 0.1 uM, p-Nitropenyl-beta-D-glucuronide: 1000 uM) in membrane vesicles from MRP4-expressing Sf9 cells2002Journal of the American Society of Nephrology : JASN, Mar, Volume: 13, Issue:3
The MRP4/ABCC4 gene encodes a novel apical organic anion transporter in human kidney proximal tubules: putative efflux pump for urinary cAMP and cGMP.
AID680181TP_TRANSPORTER: inhibition of E1S uptake (E1S: 0.05 uM, p-Nitrophenyl glucuronide: 500 uM) in Xenopus laevis oocytes2000The Journal of biological chemistry, Feb-11, Volume: 275, Issue:6
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.
AID404304Effect on human MRP2-mediated estradiol-17-beta-glucuronide transport in Sf9 cells inverted membrane vesicles relative to control2008Journal of medicinal chemistry, Jun-12, Volume: 51, Issue:11
Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (32)

TimeframeStudies, This Drug (%)All Drugs %
pre-199016 (50.00)18.7374
1990's8 (25.00)18.2507
2000's5 (15.63)29.6817
2010's3 (9.38)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.78

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 Index10.78 (24.57)
Research Supply Index3.53 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.78)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other33 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]