Page last updated: 2024-12-07

gamma-glutamine-4-nitroanilide

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Description

gamma-glutamine-4-nitroanilide: substrate for glutaminase B.; RN given refers to (L)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID81732
CHEMBL ID6251
SCHEMBL ID465891
MeSH IDM0041420

Synonyms (51)

Synonym
unii-81sz84nxws
81sz84nxws ,
ccris 8420
l-glutamic acid gamma-(4-nitroanilide), gamma-glutamyl transpeptidase substrate
n-(4-nitrophenyl)-l-glutamine
l-2-amino-4'-nitroglutaranilic acid
(s)-2-amino-5-((4-nitrophenyl)amino)-5-oxopentanoic acid
l-glutamine, n-(4-nitrophenyl)-
l-gamma-glutamyl-p-nitroanilide
gamma-glutamine-4-nitroanilide
einecs 230-748-5
gamma-glutamyl-p-nitroaniline
gamma-glutamyl-p-nitroanilide
bdbm50088537
7300-59-6
CHEMBL6251 ,
l-glutamic acid gamma-(4-nitroanilide)
nomega-(4-nitrophenyl)-l-glutamine
G0065
(2s)-2-amino-5-(4-nitroanilino)-5-oxopentanoic acid
c11h13n3o5
DTXSID9045057
SCHEMBL465891
J154.147A ,
l-.gamma.-glutamyl-p-nitroanilide
.gamma.-l-glutamyl-p-nitroanilide
.gamma.-l-glutamyl-4-nitro anilide
WMZTYIRRBCGARG-VIFPVBQESA-N
l-glutamic acid-5(4-nitroanilide)
5-(4-nitroanilino)-5-oxonorvaline #
l-.gamma.-glutyl-p-nitroanilide
FD21468
glutaranilic acid, 2-amino-4'-nitro-, l-
l-glutamic acid .gamma.-p-nitroanilide
n5-(4-nitrophenyl)-l-glutamine
l-.gamma.glu-nan
(2s)-2-amino-5-((4-nitrophenyl)amino)-5-oxopentanoic acid
.gamma.-glutamyl-p-nitroanilide
h-glu(pna)-oh
l-gamma-glutamyl-p-nitroanilide monohydrat
(s)-2-amino-5-((4-nitrophenyl)-amino)-5-oxopentanoic acid
AS-49082
Q27088423
(s)-2-amino-5-(4-nitrophenylamino)-5-oxopentanoic acid
AKOS016843231
(3-carbamoyl-1-carboxy-propyl)-(4-nitrophenyl)azanium chloride
l-|a-glutamyl-p-nitroanilide monohydrate
CS-0133138
HY-W011391A
l-glutamine,n-(4-nitrophenyl)-
l-glutamic acid gamma -(4-nitroanilide)

Research Excerpts

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Liver carboxylesterase 1Homo sapiens (human)IC50 (µMol)1,000.00000.00400.25510.6000AID1272488
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other 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]

Biological Processes (39)

Processvia Protein(s)Taxonomy
cholesterol biosynthetic processLiver carboxylesterase 1Homo sapiens (human)
cholesterol metabolic processLiver carboxylesterase 1Homo sapiens (human)
response to toxic substanceLiver carboxylesterase 1Homo sapiens (human)
positive regulation of cholesterol effluxLiver carboxylesterase 1Homo sapiens (human)
negative regulation of cholesterol storageLiver carboxylesterase 1Homo sapiens (human)
epithelial cell differentiationLiver carboxylesterase 1Homo sapiens (human)
cholesterol homeostasisLiver carboxylesterase 1Homo sapiens (human)
reverse cholesterol transportLiver carboxylesterase 1Homo sapiens (human)
medium-chain fatty acid metabolic processLiver carboxylesterase 1Homo sapiens (human)
regulation of bile acid biosynthetic processLiver carboxylesterase 1Homo sapiens (human)
cellular response to cholesterolLiver carboxylesterase 1Homo sapiens (human)
cellular response to low-density lipoprotein particle stimulusLiver carboxylesterase 1Homo sapiens (human)
cholesterol ester hydrolysis involved in cholesterol transportLiver carboxylesterase 1Homo sapiens (human)
positive regulation of cholesterol metabolic processLiver carboxylesterase 1Homo sapiens (human)
regulation of bile acid secretionLiver carboxylesterase 1Homo sapiens (human)
lipid catabolic processLiver carboxylesterase 1Homo sapiens (human)
L-cystine transportNeutral amino acid transporter AHomo sapiens (human)
amino acid transportNeutral amino acid transporter AHomo sapiens (human)
glutamine transportNeutral amino acid transporter AHomo sapiens (human)
L-alanine transportNeutral amino acid transporter AHomo sapiens (human)
L-cystine transportNeutral amino acid transporter AHomo sapiens (human)
proline transportNeutral amino acid transporter AHomo sapiens (human)
L-serine transportNeutral amino acid transporter AHomo sapiens (human)
threonine transportNeutral amino acid transporter AHomo sapiens (human)
hydroxyproline transportNeutral amino acid transporter AHomo sapiens (human)
synaptic transmission, glutamatergicNeutral amino acid transporter AHomo sapiens (human)
proline transmembrane transportNeutral amino acid transporter AHomo sapiens (human)
cognitionNeutral amino acid transporter AHomo sapiens (human)
L-aspartate import across plasma membraneNeutral amino acid transporter AHomo sapiens (human)
transport across blood-brain barrierNeutral amino acid transporter AHomo sapiens (human)
chloride transmembrane transportNeutral amino acid transporter AHomo sapiens (human)
L-serine import across plasma membraneNeutral amino acid transporter AHomo sapiens (human)
L-alanine import across plasma membraneNeutral amino acid transporter AHomo sapiens (human)
L-glutamate transmembrane transportNeutral amino acid transporter AHomo sapiens (human)
amino acid transportNeutral amino acid transporter B(0)Homo sapiens (human)
glutamine transportNeutral amino acid transporter B(0)Homo sapiens (human)
glutamine secretionNeutral amino acid transporter B(0)Homo sapiens (human)
neutral amino acid transportNeutral amino acid transporter B(0)Homo sapiens (human)
L-serine transportNeutral amino acid transporter B(0)Homo sapiens (human)
erythrocyte differentiationNeutral amino acid transporter B(0)Homo sapiens (human)
symbiont entry into host cellNeutral amino acid transporter B(0)Homo sapiens (human)
protein homotrimerizationNeutral amino acid transporter B(0)Homo sapiens (human)
L-aspartate import across plasma membraneNeutral amino acid transporter B(0)Homo sapiens (human)
transport across blood-brain barrierNeutral amino acid transporter B(0)Homo sapiens (human)
L-glutamine import across plasma membraneNeutral amino acid transporter B(0)Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (22)

Processvia Protein(s)Taxonomy
sterol esterase activityLiver carboxylesterase 1Homo sapiens (human)
methylumbelliferyl-acetate deacetylase activityLiver carboxylesterase 1Homo sapiens (human)
carboxylesterase activityLiver carboxylesterase 1Homo sapiens (human)
carboxylic ester hydrolase activityLiver carboxylesterase 1Homo sapiens (human)
L-cystine transmembrane transporter activityNeutral amino acid transporter AHomo sapiens (human)
chloride channel activityNeutral amino acid transporter AHomo sapiens (human)
amino acid transmembrane transporter activityNeutral amino acid transporter AHomo sapiens (human)
L-alanine transmembrane transporter activityNeutral amino acid transporter AHomo sapiens (human)
L-aspartate transmembrane transporter activityNeutral amino acid transporter AHomo sapiens (human)
L-cystine transmembrane transporter activityNeutral amino acid transporter AHomo sapiens (human)
L-glutamine transmembrane transporter activityNeutral amino acid transporter AHomo sapiens (human)
L-proline transmembrane transporter activityNeutral amino acid transporter AHomo sapiens (human)
L-serine transmembrane transporter activityNeutral amino acid transporter AHomo sapiens (human)
L-threonine transmembrane transporter activityNeutral amino acid transporter AHomo sapiens (human)
symporter activityNeutral amino acid transporter AHomo sapiens (human)
L-hydroxyproline transmembrane transporter activityNeutral amino acid transporter AHomo sapiens (human)
virus receptor activityNeutral amino acid transporter B(0)Homo sapiens (human)
protein bindingNeutral amino acid transporter B(0)Homo sapiens (human)
amino acid transmembrane transporter activityNeutral amino acid transporter B(0)Homo sapiens (human)
L-aspartate transmembrane transporter activityNeutral amino acid transporter B(0)Homo sapiens (human)
L-glutamine transmembrane transporter activityNeutral amino acid transporter B(0)Homo sapiens (human)
L-serine transmembrane transporter activityNeutral amino acid transporter B(0)Homo sapiens (human)
symporter activityNeutral amino acid transporter B(0)Homo sapiens (human)
antiporter activityNeutral amino acid transporter B(0)Homo sapiens (human)
ligand-gated channel activityNeutral amino acid transporter B(0)Homo sapiens (human)
signaling receptor activityNeutral amino acid transporter B(0)Homo sapiens (human)
metal ion bindingNeutral amino acid transporter B(0)Homo sapiens (human)
neutral L-amino acid transmembrane transporter activityNeutral amino acid transporter B(0)Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
cytoplasmLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulumLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulum lumenLiver carboxylesterase 1Homo sapiens (human)
lipid dropletLiver carboxylesterase 1Homo sapiens (human)
cytosolLiver carboxylesterase 1Homo sapiens (human)
lipid dropletLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulumLiver carboxylesterase 1Homo sapiens (human)
plasma membraneNeutral amino acid transporter AHomo sapiens (human)
centrosomeNeutral amino acid transporter AHomo sapiens (human)
intermediate filamentNeutral amino acid transporter AHomo sapiens (human)
plasma membraneNeutral amino acid transporter AHomo sapiens (human)
cell surfaceNeutral amino acid transporter AHomo sapiens (human)
membraneNeutral amino acid transporter AHomo sapiens (human)
melanosomeNeutral amino acid transporter AHomo sapiens (human)
synapseNeutral amino acid transporter AHomo sapiens (human)
extracellular exosomeNeutral amino acid transporter AHomo sapiens (human)
plasma membraneNeutral amino acid transporter B(0)Homo sapiens (human)
basal plasma membraneNeutral amino acid transporter B(0)Homo sapiens (human)
membraneNeutral amino acid transporter B(0)Homo sapiens (human)
melanosomeNeutral amino acid transporter B(0)Homo sapiens (human)
extracellular exosomeNeutral amino acid transporter B(0)Homo sapiens (human)
plasma membraneNeutral amino acid transporter B(0)Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID229380Ratio of kinetic constant (Kcat/KM) acting as acceptor substrate for gamma-GGT (Glutamyltranspeptidase)-mediated transpeptidation was determined in rat kidney2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
Synthesis of aza and oxaglutamyl-p-nitroanilide derivatives and their kinetic studies with gamma-glutamyltranspeptidase.
AID229382Ratio of kinetic constant (Kcat/KM) acting as donor substrate for gamma-GGT (Glutamyltranspeptidase)-mediated transpeptidation was determined in rat kidney2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
Synthesis of aza and oxaglutamyl-p-nitroanilide derivatives and their kinetic studies with gamma-glutamyltranspeptidase.
AID71596Kinetic constant acting as acceptor substrate for gamma-GGT (Glutamyltranspeptidase)-mediated transpeptidation was determined in rat kidney2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
Synthesis of aza and oxaglutamyl-p-nitroanilide derivatives and their kinetic studies with gamma-glutamyltranspeptidase.
AID71708Kinetic constant acting as donor substrate for gamma-GGT (Glutamyltranspeptidase)-mediated transpeptidation was determined in rat kidney (units are 10e3/min)2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
Synthesis of aza and oxaglutamyl-p-nitroanilide derivatives and their kinetic studies with gamma-glutamyltranspeptidase.
AID1272488Inhibition of ASCT2 (unknown origin)-mediated glutamine transport2016Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3
2-Amino-4-bis(aryloxybenzyl)aminobutanoic acids: A novel scaffold for inhibition of ASCT2-mediated glutamine transport.
AID1534334Inhibition of ASCT2 (unknown origin)2019European journal of medicinal chemistry, Feb-01, Volume: 163Discovery and development of small molecule modulators targeting glutamine metabolism.
AID71701Kinetic constant acting as donor substrate for GGT (gamma-Glutamyltranspeptidase)-mediated transpeptidation was determined in rat kidney2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
Synthesis of aza and oxaglutamyl-p-nitroanilide derivatives and their kinetic studies with gamma-glutamyltranspeptidase.
AID1272489Inhibition of ASCT2-mediated glutamine transport in rat C6 cells using [3H]-glutamine after 15 mins by scintillation counting2016Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3
2-Amino-4-bis(aryloxybenzyl)aminobutanoic acids: A novel scaffold for inhibition of ASCT2-mediated glutamine transport.
AID1225256Inhibition of ASCT2-mediated [3H]glutamine uptake in HEK293 cells after 15 mins by Live-cell glutamine uptake assay2015Bioorganic & medicinal chemistry letters, Jan-01, Volume: 25, Issue:1
2-Substituted Nγ-glutamylanilides as novel probes of ASCT2 with improved potency.
AID1272490Inhibition of ASCT2-mediated glutamine transport in human HEK293 cells using [3H]-glutamine after 15 mins by scintillation counting2016Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3
2-Amino-4-bis(aryloxybenzyl)aminobutanoic acids: A novel scaffold for inhibition of ASCT2-mediated glutamine transport.
AID71705Kinetic constant acting as acceptor substrate for gamma-GGT (Glutamyltranspeptidase)-mediated transpeptidation was determined in rat kidney (units are 10e3/min)2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
Synthesis of aza and oxaglutamyl-p-nitroanilide derivatives and their kinetic studies with gamma-glutamyltranspeptidase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (43)

TimeframeStudies, This Drug (%)All Drugs %
pre-199014 (32.56)18.7374
1990's13 (30.23)18.2507
2000's8 (18.60)29.6817
2010's7 (16.28)24.3611
2020's1 (2.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.64

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 Index10.64 (24.57)
Research Supply Index3.81 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.64)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.27%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other43 (97.73%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]