Page last updated: 2024-12-06

4-nitrohippuric acid

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

Description

4-Nitrohippuric acid is a metabolite of toluene, a common industrial solvent and component of gasoline. It is formed in the liver when toluene is metabolized by the enzyme cytochrome P450. The presence of 4-nitrohippuric acid in urine is a biomarker of toluene exposure. It is studied to assess toluene exposure in occupational settings and to monitor the effectiveness of environmental control measures. 4-Nitrohippuric acid can be synthesized through various chemical reactions, but it is primarily produced by the human body as a byproduct of toluene metabolism.'

4-nitrohippuric acid: major metabolite of 4-nitrobenzoic acid [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID17549
CHEMBL ID8682
SCHEMBL ID1285585
MeSH IDM0103512

Synonyms (62)

Synonym
nsc-33334
nsc33334
2645-07-0
SDCCGMLS-0065545.P001
OPREA1_078681
OPREA1_067067
NCGC00091799-01
p-nitrohippuric acid
n-4-nitrobenzoylglycine
ccris 6077
glycine, n-(p-nitrobenzoyl)-
hippuric acid, p-nitro-
brn 1125394
4-nitrohippuric acid
n-(p-nitrobenzoyl)glycine
nsc 33334
einecs 220-156-5
p-nitrobenzoylglycine
glycine, n-(4-nitrobenzoyl)-
[(4-nitrobenzoyl)amino]acetic acid
AKOS000200803
CHEMBL8682 ,
2-[(4-nitrobenzoyl)amino]acetic acid
n-(4-nitrobenzoyl)glycine
F0873-0006
(4-nitro-benzoylamino)-acetic acid
bdbm50016603
NCGC00091799-02
unii-9hiu46t98m
9hiu46t98m ,
4-09-00-01199 (beilstein handbook reference)
tox21_201181
NCGC00258733-01
dtxsid8025759 ,
dtxcid005759
cas-2645-07-0
FT-0634427
AKOS015889410
(4-nitrobenzoylamino)acetic acid
4-nitrobenzoylglycine
nitrohippuric acid, p-
2-(4-nitrobenzamido)acetic acid
2-((4-nitrobenzoyl)amino)acetic acid
XCMUCRMMVDSVEL-UHFFFAOYSA-N
SCHEMBL1285585
p-nitrohippursaure
sr-01000009743
SR-01000009743-1
J-016432
4-nitrohippuricacid
mfcd00007349
Q27272566
D97784
A877227
2-(4-nitrobenzamido)aceticacid
2-[(4-nitrophenyl)formamido]acetic acid
EN300-23706
SB79883
PD119724
CS-0073015
HY-W028991
Z56936638

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" 2 Reduction of 4-nitrobenzoic acid was significantly decreased by antibiotic pretreatment; the mean decrease in reduction was 81% for animals doses orally and 73% for intraperitoneally dosed marmosets."( Influence of the gut microflora on the metabolism of 4-nitrobenzoic acid in the marmoset.
James, SP; Kuzniar, EJ, 1981
)
0.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency70.79460.004023.8416100.0000AID485290
Chain A, HADH2 proteinHomo sapiens (human)Potency39.81070.025120.237639.8107AID886; AID893
Chain B, HADH2 proteinHomo sapiens (human)Potency39.81070.025120.237639.8107AID886; AID893
Chain A, CruzipainTrypanosoma cruziPotency39.81070.002014.677939.8107AID1476
interleukin 8Homo sapiens (human)Potency74.97800.047349.480674.9780AID651758
peroxisome proliferator activated receptor gammaHomo sapiens (human)Potency50.11870.001019.414170.9645AID588537
Nuclear receptor ROR-gammaHomo sapiens (human)Potency2.37100.026622.448266.8242AID651802
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Aldo-keto reductase family 1 member B1Rattus norvegicus (Norway rat)IC50 (µMol)280.00000.00041.877310.0000AID34940
[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)
Tyrosine-protein kinase LckHomo sapiens (human)Kd0.29000.00021.117424.2210AID224294
Tyrosine-protein kinase FynHomo sapiens (human)Kd0.24000.00081.42388.4000AID72281
[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 (85)

Processvia Protein(s)Taxonomy
protein phosphorylationTyrosine-protein kinase LckHomo sapiens (human)
intracellular zinc ion homeostasisTyrosine-protein kinase LckHomo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic processTyrosine-protein kinase LckHomo sapiens (human)
response to xenobiotic stimulusTyrosine-protein kinase LckHomo sapiens (human)
peptidyl-tyrosine phosphorylationTyrosine-protein kinase LckHomo sapiens (human)
hemopoiesisTyrosine-protein kinase LckHomo sapiens (human)
platelet activationTyrosine-protein kinase LckHomo sapiens (human)
T cell differentiationTyrosine-protein kinase LckHomo sapiens (human)
T cell costimulationTyrosine-protein kinase LckHomo sapiens (human)
positive regulation of heterotypic cell-cell adhesionTyrosine-protein kinase LckHomo sapiens (human)
intracellular signal transductionTyrosine-protein kinase LckHomo sapiens (human)
peptidyl-tyrosine autophosphorylationTyrosine-protein kinase LckHomo sapiens (human)
Fc-gamma receptor signaling pathwayTyrosine-protein kinase LckHomo sapiens (human)
T cell receptor signaling pathwayTyrosine-protein kinase LckHomo sapiens (human)
positive regulation of T cell receptor signaling pathwayTyrosine-protein kinase LckHomo sapiens (human)
positive regulation of T cell activationTyrosine-protein kinase LckHomo sapiens (human)
leukocyte migrationTyrosine-protein kinase LckHomo sapiens (human)
release of sequestered calcium ion into cytosolTyrosine-protein kinase LckHomo sapiens (human)
regulation of lymphocyte activationTyrosine-protein kinase LckHomo sapiens (human)
positive regulation of leukocyte cell-cell adhesionTyrosine-protein kinase LckHomo sapiens (human)
positive regulation of intrinsic apoptotic signaling pathwayTyrosine-protein kinase LckHomo sapiens (human)
innate immune responseTyrosine-protein kinase LckHomo sapiens (human)
cell surface receptor protein tyrosine kinase signaling pathwayTyrosine-protein kinase LckHomo sapiens (human)
B cell receptor signaling pathwayTyrosine-protein kinase LckHomo sapiens (human)
response to singlet oxygenTyrosine-protein kinase FynHomo sapiens (human)
neuron migrationTyrosine-protein kinase FynHomo sapiens (human)
stimulatory C-type lectin receptor signaling pathwayTyrosine-protein kinase FynHomo sapiens (human)
adaptive immune responseTyrosine-protein kinase FynHomo sapiens (human)
negative regulation of inflammatory response to antigenic stimulusTyrosine-protein kinase FynHomo sapiens (human)
heart processTyrosine-protein kinase FynHomo sapiens (human)
protein phosphorylationTyrosine-protein kinase FynHomo sapiens (human)
calcium ion transportTyrosine-protein kinase FynHomo sapiens (human)
G protein-coupled glutamate receptor signaling pathwayTyrosine-protein kinase FynHomo sapiens (human)
axon guidanceTyrosine-protein kinase FynHomo sapiens (human)
learningTyrosine-protein kinase FynHomo sapiens (human)
feeding behaviorTyrosine-protein kinase FynHomo sapiens (human)
regulation of cell shapeTyrosine-protein kinase FynHomo sapiens (human)
gene expressionTyrosine-protein kinase FynHomo sapiens (human)
negative regulation of gene expressionTyrosine-protein kinase FynHomo sapiens (human)
negative regulation of hydrogen peroxide biosynthetic processTyrosine-protein kinase FynHomo sapiens (human)
positive regulation of neuron projection developmentTyrosine-protein kinase FynHomo sapiens (human)
protein ubiquitinationTyrosine-protein kinase FynHomo sapiens (human)
peptidyl-tyrosine phosphorylationTyrosine-protein kinase FynHomo sapiens (human)
protein catabolic processTyrosine-protein kinase FynHomo sapiens (human)
forebrain developmentTyrosine-protein kinase FynHomo sapiens (human)
T cell costimulationTyrosine-protein kinase FynHomo sapiens (human)
negative regulation of protein ubiquitinationTyrosine-protein kinase FynHomo sapiens (human)
intracellular signal transductionTyrosine-protein kinase FynHomo sapiens (human)
cellular response to platelet-derived growth factor stimulusTyrosine-protein kinase FynHomo sapiens (human)
Fc-gamma receptor signaling pathway involved in phagocytosisTyrosine-protein kinase FynHomo sapiens (human)
negative regulation of protein catabolic processTyrosine-protein kinase FynHomo sapiens (human)
positive regulation of tyrosine phosphorylation of STAT proteinTyrosine-protein kinase FynHomo sapiens (human)
response to ethanolTyrosine-protein kinase FynHomo sapiens (human)
vascular endothelial growth factor receptor signaling pathwayTyrosine-protein kinase FynHomo sapiens (human)
ephrin receptor signaling pathwayTyrosine-protein kinase FynHomo sapiens (human)
dendrite morphogenesisTyrosine-protein kinase FynHomo sapiens (human)
regulation of peptidyl-tyrosine phosphorylationTyrosine-protein kinase FynHomo sapiens (human)
activated T cell proliferationTyrosine-protein kinase FynHomo sapiens (human)
modulation of chemical synaptic transmissionTyrosine-protein kinase FynHomo sapiens (human)
T cell receptor signaling pathwayTyrosine-protein kinase FynHomo sapiens (human)
leukocyte migrationTyrosine-protein kinase FynHomo sapiens (human)
detection of mechanical stimulus involved in sensory perception of painTyrosine-protein kinase FynHomo sapiens (human)
cellular response to hydrogen peroxideTyrosine-protein kinase FynHomo sapiens (human)
cellular response to transforming growth factor beta stimulusTyrosine-protein kinase FynHomo sapiens (human)
positive regulation of protein targeting to membraneTyrosine-protein kinase FynHomo sapiens (human)
dendritic spine maintenanceTyrosine-protein kinase FynHomo sapiens (human)
positive regulation of protein localization to nucleusTyrosine-protein kinase FynHomo sapiens (human)
regulation of glutamate receptor signaling pathwayTyrosine-protein kinase FynHomo sapiens (human)
negative regulation of oxidative stress-induced intrinsic apoptotic signaling pathwayTyrosine-protein kinase FynHomo sapiens (human)
negative regulation of dendritic spine maintenanceTyrosine-protein kinase FynHomo sapiens (human)
response to amyloid-betaTyrosine-protein kinase FynHomo sapiens (human)
cellular response to amyloid-betaTyrosine-protein kinase FynHomo sapiens (human)
cellular response to L-glutamateTyrosine-protein kinase FynHomo sapiens (human)
cellular response to glycineTyrosine-protein kinase FynHomo sapiens (human)
positive regulation of protein localization to membraneTyrosine-protein kinase FynHomo sapiens (human)
regulation of calcium ion import across plasma membraneTyrosine-protein kinase FynHomo sapiens (human)
positive regulation of cysteine-type endopeptidase activityTyrosine-protein kinase FynHomo sapiens (human)
innate immune responseTyrosine-protein kinase FynHomo sapiens (human)
cell differentiationTyrosine-protein kinase FynHomo sapiens (human)
cell surface receptor protein tyrosine kinase signaling pathwayTyrosine-protein kinase FynHomo sapiens (human)
negative regulation of transcription by RNA polymerase IINuclear receptor ROR-gammaHomo sapiens (human)
xenobiotic metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
regulation of glucose metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
regulation of steroid metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
intracellular receptor signaling pathwayNuclear receptor ROR-gammaHomo sapiens (human)
circadian regulation of gene expressionNuclear receptor ROR-gammaHomo sapiens (human)
cellular response to sterolNuclear receptor ROR-gammaHomo sapiens (human)
positive regulation of circadian rhythmNuclear receptor ROR-gammaHomo sapiens (human)
regulation of fat cell differentiationNuclear receptor ROR-gammaHomo sapiens (human)
positive regulation of DNA-templated transcriptionNuclear receptor ROR-gammaHomo sapiens (human)
adipose tissue developmentNuclear receptor ROR-gammaHomo sapiens (human)
T-helper 17 cell differentiationNuclear receptor ROR-gammaHomo sapiens (human)
regulation of transcription by RNA polymerase IINuclear receptor ROR-gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (38)

Processvia Protein(s)Taxonomy
phosphotyrosine residue bindingTyrosine-protein kinase LckHomo sapiens (human)
protein tyrosine kinase activityTyrosine-protein kinase LckHomo sapiens (human)
non-membrane spanning protein tyrosine kinase activityTyrosine-protein kinase LckHomo sapiens (human)
protein serine/threonine phosphatase activityTyrosine-protein kinase LckHomo sapiens (human)
protein bindingTyrosine-protein kinase LckHomo sapiens (human)
ATP bindingTyrosine-protein kinase LckHomo sapiens (human)
phospholipase activator activityTyrosine-protein kinase LckHomo sapiens (human)
protein kinase bindingTyrosine-protein kinase LckHomo sapiens (human)
protein phosphatase bindingTyrosine-protein kinase LckHomo sapiens (human)
SH2 domain bindingTyrosine-protein kinase LckHomo sapiens (human)
T cell receptor bindingTyrosine-protein kinase LckHomo sapiens (human)
CD4 receptor bindingTyrosine-protein kinase LckHomo sapiens (human)
CD8 receptor bindingTyrosine-protein kinase LckHomo sapiens (human)
identical protein bindingTyrosine-protein kinase LckHomo sapiens (human)
phospholipase bindingTyrosine-protein kinase LckHomo sapiens (human)
phosphatidylinositol 3-kinase bindingTyrosine-protein kinase LckHomo sapiens (human)
ATPase bindingTyrosine-protein kinase LckHomo sapiens (human)
signaling receptor bindingTyrosine-protein kinase LckHomo sapiens (human)
protein tyrosine kinase activityTyrosine-protein kinase FynHomo sapiens (human)
non-membrane spanning protein tyrosine kinase activityTyrosine-protein kinase FynHomo sapiens (human)
protein bindingTyrosine-protein kinase FynHomo sapiens (human)
ATP bindingTyrosine-protein kinase FynHomo sapiens (human)
phospholipase activator activityTyrosine-protein kinase FynHomo sapiens (human)
enzyme bindingTyrosine-protein kinase FynHomo sapiens (human)
type 5 metabotropic glutamate receptor bindingTyrosine-protein kinase FynHomo sapiens (human)
identical protein bindingTyrosine-protein kinase FynHomo sapiens (human)
alpha-tubulin bindingTyrosine-protein kinase FynHomo sapiens (human)
phospholipase bindingTyrosine-protein kinase FynHomo sapiens (human)
transmembrane transporter bindingTyrosine-protein kinase FynHomo sapiens (human)
metal ion bindingTyrosine-protein kinase FynHomo sapiens (human)
ephrin receptor bindingTyrosine-protein kinase FynHomo sapiens (human)
tau protein bindingTyrosine-protein kinase FynHomo sapiens (human)
tau-protein kinase activityTyrosine-protein kinase FynHomo sapiens (human)
growth factor receptor bindingTyrosine-protein kinase FynHomo sapiens (human)
scaffold protein bindingTyrosine-protein kinase FynHomo sapiens (human)
disordered domain specific bindingTyrosine-protein kinase FynHomo sapiens (human)
signaling receptor bindingTyrosine-protein kinase FynHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription factor activityNuclear receptor ROR-gammaHomo sapiens (human)
protein bindingNuclear receptor ROR-gammaHomo sapiens (human)
oxysterol bindingNuclear receptor ROR-gammaHomo sapiens (human)
zinc ion bindingNuclear receptor ROR-gammaHomo sapiens (human)
ligand-activated transcription factor activityNuclear receptor ROR-gammaHomo sapiens (human)
sequence-specific double-stranded DNA bindingNuclear receptor ROR-gammaHomo sapiens (human)
nuclear receptor activityNuclear receptor ROR-gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (21)

Processvia Protein(s)Taxonomy
pericentriolar materialTyrosine-protein kinase LckHomo sapiens (human)
immunological synapseTyrosine-protein kinase LckHomo sapiens (human)
cytosolTyrosine-protein kinase LckHomo sapiens (human)
plasma membraneTyrosine-protein kinase LckHomo sapiens (human)
membrane raftTyrosine-protein kinase LckHomo sapiens (human)
extracellular exosomeTyrosine-protein kinase LckHomo sapiens (human)
plasma membraneTyrosine-protein kinase LckHomo sapiens (human)
membrane raftTyrosine-protein kinase FynHomo sapiens (human)
dendriteTyrosine-protein kinase FynHomo sapiens (human)
nucleusTyrosine-protein kinase FynHomo sapiens (human)
mitochondrionTyrosine-protein kinase FynHomo sapiens (human)
endosomeTyrosine-protein kinase FynHomo sapiens (human)
cytosolTyrosine-protein kinase FynHomo sapiens (human)
actin filamentTyrosine-protein kinase FynHomo sapiens (human)
plasma membraneTyrosine-protein kinase FynHomo sapiens (human)
postsynaptic densityTyrosine-protein kinase FynHomo sapiens (human)
dendriteTyrosine-protein kinase FynHomo sapiens (human)
perikaryonTyrosine-protein kinase FynHomo sapiens (human)
cell bodyTyrosine-protein kinase FynHomo sapiens (human)
membrane raftTyrosine-protein kinase FynHomo sapiens (human)
perinuclear region of cytoplasmTyrosine-protein kinase FynHomo sapiens (human)
perinuclear endoplasmic reticulumTyrosine-protein kinase FynHomo sapiens (human)
glial cell projectionTyrosine-protein kinase FynHomo sapiens (human)
Schaffer collateral - CA1 synapseTyrosine-protein kinase FynHomo sapiens (human)
plasma membraneTyrosine-protein kinase FynHomo sapiens (human)
nucleusNuclear receptor ROR-gammaHomo sapiens (human)
nucleoplasmNuclear receptor ROR-gammaHomo sapiens (human)
nuclear bodyNuclear receptor ROR-gammaHomo sapiens (human)
chromatinNuclear receptor ROR-gammaHomo sapiens (human)
nucleusNuclear receptor ROR-gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID34940Inhibition of aldose reductase from rat lens. Value ranges from 140 - 5801989Journal of medicinal chemistry, May, Volume: 32, Issue:5
Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety.
AID388272Activity of rat recombinant peptidylglycine alpha-amidating monooxygenase assessed as stimulation of oxygen consumption2008Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23
Substituted hippurates and hippurate analogs as substrates and inhibitors of peptidylglycine alpha-hydroxylating monooxygenase (PHM).
AID72281Dissociation constant for binding to SH2 domain of Fyn protein kinase1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Acquisition of high-affinity, SH2-targeted ligands via a spatially focused library.
AID388274Ratio of Vm(app) to Km(app) for rat recombinant peptidylglycine alpha-amidating monooxygenase relative to hippuric acid2008Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23
Substituted hippurates and hippurate analogs as substrates and inhibitors of peptidylglycine alpha-hydroxylating monooxygenase (PHM).
AID224294Dissociation constant for binding to SH2 domain of p56 lck tyrosine kinase1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Acquisition of high-affinity, SH2-targeted ligands via a spatially focused library.
AID35127Inhibition of partially purified aldose reductase obtained from rat lens (100 uM ); ND is No Data1989Journal of medicinal chemistry, May, Volume: 32, Issue:5
Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety.
AID388273Ratio of Vm(app) to Km(app) for rat recombinant peptidylglycine alpha-amidating monooxygenase2008Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23
Substituted hippurates and hippurate analogs as substrates and inhibitors of peptidylglycine alpha-hydroxylating monooxygenase (PHM).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (60.00)18.7374
1990's1 (20.00)18.2507
2000's1 (20.00)29.6817
2010's0 (0.00)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: 12.42

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 Index12.42 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.21 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.42)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]