Page last updated: 2024-12-06

4-nitrophenylgalactoside

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

Description

4-Nitrophenyl-β-D-galactopyranoside (4-NPgal) is a synthetic substrate for β-galactosidase. It is commonly used to measure β-galactosidase activity due to the release of the colored product, 4-nitrophenol, upon hydrolysis by the enzyme. The compound is synthesized by reacting 4-nitrophenol with galactose in the presence of a catalyst. 4-NPgal is a valuable tool for studying the kinetics and mechanism of β-galactosidase activity. Its hydrolysis is also used as a reporter gene assay for monitoring gene expression and cellular function.'

4-nitrophenylgalactoside: RN refers to (beta-D)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

4-nitrophenyl-beta-D-galactoside : A beta-D-galactopyranoside 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 CID65115
CHEMBL ID157265
CHEBI ID355715
SCHEMBL ID135783
MeSH IDM0164760

Synonyms (57)

Synonym
3150-24-1
p-nitrophenol galactoside
4-nitrophenyl galactoside
p-nitrophenyl beta-d-galactopyranoside
4-nitrophenyl |a-d-galactopyranoside
4-nitrophenyl beta-d-galactopyranoside
C04452
4-nitrophenol-alpha-d-galactopyranoside
4-nitrophenyl beta-d-galacto??pyran??oside, >=98% (enzymatic)
1-o-(4-nitrophenyl)-beta-d-galactopyranose
4-nitrophenyl-beta-d-galactoside
p-nitrophenyl-beta-d-galactoside
4-nitrophenylgalactoside
DB02632
1-o-(p-nitrophenyl)-beta-d-galactose
1-o-(4-nitrophenyl)-beta-d-galactose
1-o-(p-nitrophenyl)-beta-d-galactopyranose
4-nitrophenyl-beta-d-galactopyranoside
1-o-[p-nitrophenyl]-beta-d-galactopyranose
pnpbetagal
CHEBI:355715 ,
CHEMBL157265 ,
N0616
nsc 89287
beta-d-galactopyranoside, 4-nitrophenyl
einecs 221-584-5
galactopyranoside, p-nitrophenyl, beta-d-
p-nitrophenyl beta-d-galactoside (van)
AKOS015902896
AKOS015856186
4-nitrophenyl beta-d-galacto-pyran-oside
SCHEMBL135783
3ZYF
(2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-(4-nitrophenoxy)tetrahydropyran-3,4,5-triol
4-nitrophenyl hexopyranoside #
W-201755
4-nitrophenyl b-d-galactopyranoside hydrate
galactopyranoside, p-nitrophenyl, .beta.-d-
AC-24637
mfcd00063256
4-nitrophenyl i(2)-d-galactopyranoside hydrate
4-nitrophenyl-i(2)-d-galactopyranoside
DTXSID40185401
4-nitrophenyl-?-d-galactopyranoside
4-nitrophenyl -d-galactoside-(1,5)
F20487
Q27093594
AS-18092
4-nitrophenyl -d-galactopyranoside
b-d-galactopyranoside, 4-nitrophenyl
p-nitrophenyl-?-d-galactopyranoside
p-nitrophenyl ?-d-galactopyranoside
4-nitrophenyl beta -d-galactopyranoside
HY-137550
bdbm50591293
wurcs=2.0/1,1,0/[a2112h-1b_1-5_1*o(c^ec^zc^ec^ec^zc^e$3)/6no/9=o]/1/
CS-0139874

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"Active absorption in the intestine and metabolism of the beta- and alpha-anomers of the glucoside and galactoside of p-nitrophenol (p-NP) were studied to find a more suitable prodrug for poorly absorbed drugs."( Comparative study of active absorption by the intestine and disposition of anomers of sugar-conjugated compounds.
Awazu, S; Hayashi, M; Mizuma, T; Ohta, K, 1993
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
affinity labelAn enzyme inhibitor, generally irreversible, that is similar in structure to a particular substrate for a specific enzyme.
[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-galactosideAny D-galactoside having beta-configuration at its anomeric centre.
monosaccharide derivativeA carbohydrate derivative that is formally obtained from a monosaccharide.
[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 (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, PA-I galactophilic lectinPseudomonas aeruginosa PAO1Kd14.100014.100014.100014.1000AID977611
Chain A, Pa-i Galactophilic LectinPseudomonas aeruginosa PAO1Kd14.100014.100014.100014.1000AID977611
Chain A, PA-I galactophilic lectinPseudomonas aeruginosa PAO1Kd14.100014.100014.100014.1000AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID190824Total activity of the entire contents of DSI segment in rat intestine1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Drug glycosides: potential prodrugs for colon-specific drug delivery.
AID190826Total activity of the entire contents of cecum segment in rat intestine1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Drug glycosides: potential prodrugs for colon-specific drug delivery.
AID381597Inhibition of Cryptosporidium parvum recombinant Galactose/N-acetylgalactosamine-specific lectin binding to Caco2A cells relative to galactose2007The Journal of biological chemistry, Nov-30, Volume: 282, Issue:48
Cryptosporidium p30, a galactose/N-acetylgalactosamine-specific lectin, mediates infection in vitro.
AID1681526Inhibition of Pseudomonas aeruginosa ATCC 33347 LecA expressed in Escherichia coli BL21(DE3) cells incubated for 30 to 60 mins by (N-(fluorescein-5-yl)-N'-(beta-D-(m-aminophenyl)-galactopyranosyl)thiocarbamide) reporter based fluorescence polarization ass2020Journal of medicinal chemistry, 10-22, Volume: 63, Issue:20
Directing Drugs to Bugs: Antibiotic-Carbohydrate Conjugates Targeting Biofilm-Associated Lectins of
AID191620Specific activity of the stomach segment in rat intestine1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Drug glycosides: potential prodrugs for colon-specific drug delivery.
AID381596Inhibition of Cryptosporidium parvum recombinant Galactose/N-acetylgalactosamine-specific lectin binding to Caco2A cells2007The Journal of biological chemistry, Nov-30, Volume: 282, Issue:48
Cryptosporidium p30, a galactose/N-acetylgalactosamine-specific lectin, mediates infection in vitro.
AID190825Total activity of the entire contents of PSI segment in rat intestine1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Drug glycosides: potential prodrugs for colon-specific drug delivery.
AID191618Specific activity of the PSI segment in rat intestine1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Drug glycosides: potential prodrugs for colon-specific drug delivery.
AID190827Total activity of the entire contents of stomach segment in rat intestine1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Drug glycosides: potential prodrugs for colon-specific drug delivery.
AID22831Vmax value was determined in homogenates of pooled cecal contents in rats1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Drug glycosides: potential prodrugs for colon-specific drug delivery.
AID191619Specific activity of the cecum segment in rat intestine1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Drug glycosides: potential prodrugs for colon-specific drug delivery.
AID191617Specific activity of the DSI segment in rat intestine1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Drug glycosides: potential prodrugs for colon-specific drug delivery.
AID1857386Competitive binding affinity to recombinant Pseudomonas aeruginosa LecA expressed in Escherichia coli BL21(DE3) incubated for 30 to 60 mins by fluorescent polarization assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Lectin-Targeted Prodrugs Activated by
AID18316Km(app) value was determined in homogenates of pooled cecal contents in rats1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Drug glycosides: potential prodrugs for colon-specific drug delivery.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2011Angewandte Chemie (International ed. in English), Nov-04, Volume: 50, Issue:45
A glycopeptide dendrimer inhibitor of the galactose-specific lectin LecA and of Pseudomonas aeruginosa biofilms.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (93)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (5.38)18.7374
1990's37 (39.78)18.2507
2000's25 (26.88)29.6817
2010's21 (22.58)24.3611
2020's5 (5.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.75

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 Index10.75 (24.57)
Research Supply Index4.55 (2.92)
Research Growth Index5.30 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.75)

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%
Other94 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]