p-Nitroaniline

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H6N2O2
Molecular Weight	138.124
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=CC=C(C=C1)[N+]([O-])=O

InChI

InChIKey=TYMLOMAKGOJONV-UHFFFAOYSA-N

InChI=1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19811921 | https://www.mpbio.com/product.php?pid=02190253&country=223

P-nitroaniline is a chromogenic molecule that is used as a dyestuff intermediate in industrial applications. In biochemical research, enzyme assays utilize modified aminoacyl or peptidyl p-nitroanilines as substrates. The enzyme catalyzes the release of free p-nitroaniline, which is the basis of the colorimetric determination of the enzyme activity. Applications of the colorimetric properties of p-nitroanilide include the design of biopolymer drug delivery systems and of solid supports for enzyme immobilization. A kinetic analysis of the α-chymotrypsin catalyzed hydrolysis of aminoacyl and peptidyl p-nitroanilide substrates in vesicles has been reported. It has been shown to possess anti-leishmanial activity.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Leishmania infantum 3 Target ID: CHEMBL612848 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19811921	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Leishmaniasis 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19811921	Curative		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Low-temperature photoluminescence of p-nitroaniline and o-methyl-p-nitroaniline crystals.	2007-08	17129754
E2F-1 induces melanoma cell apoptosis via PUMA up-regulation and Bax translocation.	2007-01-30	17263886
Study of static and dynamic first hyperpolarizabilities using time-dependent density functional quadratic response theory with local contribution and natural bond orbital analysis.	2006-12-21	17190541
Resonance Raman intensity analysis of the excited state proton transfer dynamics of 2-nitrophenol in the charge-transfer band absorption.	2006-12-07	17166032
SHG active crystals of a remote functionalized achiral NLO-phore assembled through zinc(II) complexation.	2006-11-27	17112272
Study on the vibrational energy relaxation of p-nitroaniline, N,N-dimethyl-p-nitroaniline, and azulene by the transient grating method.	2006-11-21	17129132
A new colorimetric assay for methionyl aminopeptidases: examination of the binding of a new class of pseudopeptide analog inhibitors.	2006-10-01	16844071
Sensitive determination of carbohydrates labelled with p-nitroaniline by capillary electrophoresis with photometric detection using a 406 nm light-emitting diode.	2006-10	16983631
Computer simulation of the linear and nonlinear optical susceptibilities of p-nitroaniline in cyclohexane, 1,4-dioxane, and tetrahydrofuran in quadrupolar approximation. II. Local field effects and optical susceptibilitities.	2006-09-21	16970482
Combinatorial self-assembly of cyclophilin hCyp-18 ligands through rhenium coordination.	2006-09	16835860
Problems in the comparison of theoretical and experimental hyperpolarizabilities revisited.	2006-07-07	16863315
Dipeptidyl peptidase II and leukocyte cell death.	2006-06-28	16725115
Water solvent effect on the first hyperpolarizability of p-nitrophenol and p-nitrophenylphosphate: a time-dependent density functional study.	2006-05-07	16689578
In vitro characterization of an in situ microdialysis sampling assay for elastase activity detection.	2006-03-18	16242888
Structure and dipole moments of the two distinct solvated forms of p-nitroaniline in acetonitrile/CCl4 as studied by infrared electroabsorption spectroscopy.	2006-03-16	16526657
Geometries and properties of excited states in the gas phase and in solution: theory and application of a time-dependent density functional theory polarizable continuum model.	2006-03-07	16526845
Matrix isolation and computational study of the photochemistry of p-azidoaniline.	2006-02-14	16482312
Paenidase, a novel D-aspartyl endopeptidase from Paenibacillus sp. B38: purification and substrate specificity.	2006-02	16452307
Separation and determination of sugars by reversed-phase high-performance liquid chromatography after pre-column microwave-assisted derivatization.	2006-02	16372183
Studies of selenium in environmental samples and synthetic mixtures by spectrophotometry.	2006-02	16040081
Dynamics of p-nitroaniline molecules in micoporous aluminophosphate AlPO4-5 studied by solid-state NMR.	2006-01-12	16471504
Dynamical arrest of electron transfer reorganization in super-cooled water.	2005-11-30	16305214
Reduced flavin: NMR investigation of N5-H exchange mechanism, estimation of ionisation constants and assessment of properties as biological catalyst.	2005-11-25	16309555
Nonlinear response theory with relaxation: the first-order hyperpolarizability.	2005-11-15	16321072
Computer simulation of the linear and nonlinear optical susceptibilities of p-nitroaniline in cyclohexane, 1,4-dioxane, and tetrahydrofuran in quadrupolar approximation. I. Molecular polarizabilities and hyperpolarizabilities.	2005-11-10	16838931
Nonnatural amino acid incorporation into the methionine 214 position of the metzincin Pseudomonas aeruginosa alkaline protease.	2005-10-12	16221305
Second-harmonic generation of solvated molecules using multiconfigurational self-consistent-field quadratic response theory and the polarizable continuum model.	2005-10-08	16238384
Equilibrium and kinetic studies on the adsorption of aniline compounds from aqueous phase onto bifunctional polymeric adsorbent with sulfonic groups.	2005-10	16202803
Collagen production in cardiac fibroblasts during inhibition of aminopeptidase B.	2005-09	16470485
An unusual feature of end-substituted model carbon (6,0) nanotubes.	2005-09	15889290
The first hyperpolarizability of p-nitroaniline in 1,4-dioxane: a quantum mechanical/molecular mechanics study.	2005-08-15	16229570
Optimization of nonlinear optical properties by substituent position, geometry and symmetry of the molecule: An ab initio study.	2005-07-28	16852770
Energy flow in push-pull chromophores: vibrational dynamics in para-nitroaniline.	2005-06-13	15883968
Detection and quantification of leucyl aminopeptidase after native electrophoresis using leucine-p-nitroanilide.	2005-06	15920779
Protonated nitro group: structure, energy and conjugation.	2005-05-21	15889165
Electrochemically controlled hydrogen bonding. Nitrobenzenes as simple redox-dependent receptors for arylureas.	2005-05-04	15853350
Characterization of some synthetic Ru and Ir complexes by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2005-05	15739157
Insertion of dipolar molecules in channels of a centrosymmetric organic zeolite: molecular modeling and experimental investigations on diffusion and polarity formation.	2005-04-28	16851930
The mechanistic origin of regiochemical changes in the nitrosative N-dealkylation of N,N-dialkyl aromatic amines.	2005-03-21	15750654
Systematic study of the structure-property relationship of a series of ferrocenyl nonlinear optical chromophores.	2005-03-02	15725034
Micell-mediated extraction for the spectrophotometric determination of nitrite in water and biological samples based on its reaction with p-nitroaniline in the presence of diphenylamine.	2005-01-15	15620895
Reversal of angiotensin II-stimulated collagen gel contraction in cardiac fibroblasts by aminopeptidase inhibition.	2005-01	15613982
Altered specificity of Hint-W123Q supports a role for Hint inhibition by ASW in avian sex determination.	2004-12-15	15507519
Effect of bestatin on angiotensin I-, II- and III-induced collagen gel contraction in cardiac fibroblasts.	2004-12	15803436
Ion soft-landing into liquids: Protein identification, separation, and purification with retention of biological activity.	2004-12	15589764
Regional phospholipid analysis of porcine lens membranes by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2004-12	15578747
Spectrophotometric determination of hydroxylamine and its derivatives in pharmaceuticals.	2004-12	15577248
[Synthesis and anti-inflammatory activity of N-(4-arylamidophenyl) methanesulfonamide derivatives].	2004-07	15493840
Production of extracellular proteases by human pathogenic Trichoderma longibrachiatum strains.	2004	15571068
Effects of ionizable organic compounds in different species on the sorption of p-nitroaniline to sediment.	2003-11-13	15644236

Patents

Sample Use Guides

In Vivo Use Guide

In a Balb/c mice model of L. Infantum, administration of P-nitroaniline (5mg/kg/day for 10 days, injected ip route) led to a clear-cut parasite burden reduction (ca. 99%).

Route of Administration: Intraperitoneal

In Vitro Use Guide

The saturation of Porcine prolyl oligopeptidase (POP) (176 ug/ml) was reached at around 90 uM concentration of P-nitroaniline. Km = 27 uM was the concentration of the substrate P-nitroaniline at which the reaction proceeded at the half-maximal velocity.

Name

Type

Language

p-Nitroaniline

Common Name

English

4-NITROANILINE

Preferred Name

English

NITROANILINE, P-

Common Name

English

4-NITROANILINE [HSDB]

Common Name

English

P-NITROANILINE [MI]

Common Name

English

NSC-9797

Code

English

4-NITROBENZENAMINE

Systematic Name

English

Code System Code Type Description

HSDB

1156