O-DINITROBENZENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H4N2O4
Molecular Weight	168.107
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=IZUKQUVSCNEFMJ-UHFFFAOYSA-N

InChI=1S/C6H4N2O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H

HIDE SMILES / InChI

Molecular Formula	C6H4N2O4
Molecular Weight	168.107
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: DOI: 10.1002/3527600418.mb2515454isme0001
Curator's Comment: description was created based on several sources, including: http://www.drugfuture.com/chemdata/Dinitrobenzene.html https://en.wikipedia.org/wiki/Dinitrobenzene

Dinitrobenzene (DNB) production yields a mixture of the three isomers. The ortho-isomer (o-DNB) forms colourless to yellow monoclinic plates. o-DNB is a substrate for glutathione-S-aryltransferase. The rapidity of the reaction suggests that this is the main pathway of metabolic o-DNB breakdown in the intact rat liver. o-DNB produced relevant amounts of metHb in human erythrocytes. Dinitrobenzene are used in dyes manufacture, explosives and plastics production.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutathione S-transferase A class 1 Target ID: Glutathione S-transferase A class Sources: https://www.ncbi.nlm.nih.gov/pubmed/14620531 \| DOI: 10.1002/3527600418.mb2515454isme0001	Substrate 661
Glutathione S-transferase µ class 1 Target ID: Glutathione S-transferase µ class Sources: https://www.ncbi.nlm.nih.gov/pubmed/14620531 \| DOI: 10.1002/3527600418.mb2515454isme0001	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Intracerebral hemorrhage induces edema and oxidative stress and alters N-methyl-D-aspartate receptor subunits expression.	2005	16463894
Intramolecular nitro-assisted proton transfer in photoirradiated 2-(2',4'-dinitrobenzyl)pyridine: polarized optical spectroscopic study and electronic structure calculations.	2005 Aug 18	16834092
Spectroscopic investigations of solvent effect on chiral interactions.	2005 Jun 30	16852562
Modification of Cepsilon mRNA expression by EBV-encoded latent membrane protein 1.	2006	17392589
Three-dimensional morphology and gene expression in the Drosophila blastoderm at cellular resolution I: data acquisition pipeline.	2006	17184546
Iron-induced oxidative brain injury after experimental intracerebral hemorrhage.	2006	16671453
Dinitrophenyl ligand substrates and their application to immunosensors.	2006 Jul 15	16414258
Boron dipyrromethene dyes: a rational avenue for sensing and light emitting devices.	2006 Jun 21	16751901
Development of dinitrophenylated cyclodextrin derivatives for enhanced enantiomeric separations by high-performance liquid chromatography.	2006 May 19	16620856
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Glucosamine prevents in vitro collagen degradation in chondrocytes by inhibiting advanced lipoxidation reactions and protein oxidation.	2007	17686167
Absence of functional peroxisome proliferator-activated receptor-alpha enhanced ileum permeability during experimental colitis.	2007 Aug	17515853
Rod1, an arrestin-related protein, is phosphorylated by Snf1-kinase in Saccharomyces cerevisiae.	2007 Dec 14	17949685
Rab27b regulates mast cell granule dynamics and secretion.	2007 Jul	17587407
Improved systemic pharmacokinetics, biodistribution, and antitumor activity of CpG oligodeoxynucleotides complexed to endogenous antibodies in vivo.	2007 Jul 16	17509715
[A new approach to the use of fluorogenic dinitrophenyl-containing substrates for determining the proteolytic activity of aspartyl proteinases].	2007 Jul-Aug	17929570
A new approach for distinguishing cathepsin E and D activity in antigen-processing organelles.	2007 Jun	17521331
Dinitrophenyl derivatization of imino acids, spectral characteristics and HPLC analysis: application in urinary peptide-derived hydroxyproline and proline assay.	2007 Mar	17362582
Folate-targeted dinitrophenyl hapten immunotherapy: effect of linker chemistry on antitumor activity and allergic potential.	2007 Sep-Oct	17784727
Fluorescence affinity sensing by using a self-contained fluid manoeuvring microfluidic chip.	2008 Apr	18365120
Biliprotein maturation: the chromophore attachment.	2008 Apr	18284595
N-(2,4-Dinitro-phen-yl)dehydro-abietyl-amine.	2008 Apr 23	21202372
Evaluation of behavioural and antioxidant activity of Cytisus scoparius Link in rats exposed to chronic unpredictable mild stress.	2008 Apr 24	18435835
Inhibition of the antigen-induced activation of RBL-2H3 cells by Gab2 siRNA.	2008 Dec	19118509
1-(2,4-Dinitro-phen-yl)-5-ferrocenyl-3-methyl-1H-pyrazole.	2008 Jan 4	21201250
13C and 15N NMR chemical shifts of 1-(2',4'-dinitrophenyl) and 1-(2',4',6'-trinitrophenyl) pyrazoles in the solid state and in solution.	2008 Jul	18383432
Inhibition of the antigen-induced activation of RBL-2H3 cells by sinomenine.	2008 Mar	18279805
Whole-cell cancer vaccination: from autologous to allogeneic tumor- and dendritic cell-based vaccines.	2008 Oct	18523771
Divergence of catalytic mechanism within a glycosidase family provides insight into evolution of carbohydrate metabolism by human gut flora.	2008 Oct 20	18848471
Development of automated brightfield double in situ hybridization (BDISH) application for HER2 gene and chromosome 17 centromere (CEN 17) for breast carcinomas and an assay performance comparison to manual dual color HER2 fluorescence in situ hybridization (FISH).	2008 Oct 22	18945356
Analytical and preparative enantioseparation of DL-penicillamine and DL-cysteine by high-performance liquid chromatography on alpha-acid glycoprotein and beta-cyclodextrin columns using ninhydrin as a reversible tagging reagent.	2009 Apr 10	19246042
Advancing drug innovation for neglected diseases-criteria for lead progression.	2009 Aug 25	19707561
Human CD34/CD90 ASCs are capable of growing as sphere clusters, producing high levels of VEGF and forming capillaries.	2009 Aug 6	19657392
Nanoparticle-mediated IgE-receptor aggregation and signaling in RBL mast cells.	2009 Dec 2	19929020
Association mechanism of S-dinitrophenyl glutathione with two glutathione peroxidase mimics: 2, 2 cent-ditelluro- and 2, 2 cent-diseleno-bridged b-cyclodextrins.	2009 Feb 25	19255549
Role of protein haptenation in triggering maturation events in the dendritic cell surrogate cell line THP-1.	2009 Jul 15	19427879
Folate-targeted hapten immunotherapy of adjuvant-induced arthritis: comparison of hapten potencies.	2009 Jul-Aug	19374407
Identification of a public CDR3 motif and a biased utilization of T-cell receptor V beta and J beta chains in HLA-A2/Melan-A-specific T-cell clonotypes of melanoma patients.	2009 Mar 24	19317896
High-performance liquid chromatographic enantioseparation of methanobenzazocines.	2009 Nov 6	19801151
Comparative application of microwave, ultrasonication, ultracentrifugation and conventional heating for preparation of sample as dinitrophenyl derivative for direct enantioseparation of certain amino alcohols and 1-amino-2-propanol from vitamin B12 hydrolysate on alpha1-acid glycoprotein and beta-cyclodextrin columns.	2009 Nov 6	19800629
Strategy to prevent drug-related hypersensitivity in folate-targeted hapten immunotherapy of cancer.	2009 Sep	19728104
17-allyamino-17-demethoxygeldanamycin treatment results in a magnetic resonance spectroscopy-detectable elevation in choline-containing metabolites associated with increased expression of choline transporter SLC44A1 and phospholipase A2.	2010	20946630
IL-33 is produced by mast cells and regulates IgE-dependent inflammation.	2010 Aug 3	20689814
Ovarian cancer immunotherapy: opportunities, progresses and challenges.	2010 Feb 10	20146807
Nestin is essential for zebrafish brain and eye development through control of progenitor cell apoptosis.	2010 Feb 19	20174467
Proteomic approaches to oxidative protein modifications implicated in the mechanism of aging.	2010 Jul	20590839
Regulator of g protein signaling 3 modulates wnt5b calcium dynamics and somite patterning.	2010 Jul 8	20628572
Tracking human contact allergens: from mass spectrometric identification of peptide-bound reactive small chemicals to chemical-specific naive human T-cell priming.	2010 Oct	20631061
Deficiency of activating Fcγ-receptors reduces hepatic clearance and deposition of IC and increases CIC levels in mercury-induced autoimmunity.	2010 Oct 15	20976163
Ways and means of coping with uncertainties of the relationship of the genetic blue print to protein structure and function in the cell.	2010 Sep 17	20849616

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Under aerobic conditions the main degradation pathway of o-DNB in the hepatocytes was the reduction to S-(2-nitrophenyl)-glutathione (48.1 ± 5.5 %) and to a lesser extent to o-nitroaniline (29.5 ± 2.1 %) after 2 minutes incubation.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:02:18 GMT 2023` Edited by `admin` on `Sat Dec 16 02:02:18 GMT 2023`
Record UNII	35XUO924Y0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

O-DINITROBENZENE

Common Name

English

NSC-60682

Code

English

BENZENE, O-DINITRO-

Common Name

English

ORTHO-DINITROBENZENE

Systematic Name

English

O-DINITROBENZENE [MI]

Common Name

English

1,2-DINITROBENZENE

Systematic Name

English

Code System Code Type Description

CAS

528-29-0