2,4-Dinitrophenol
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Basic Info
| Common Name | 2,4-Dinitrophenol(F03338) |
| 2D Structure | |
| Description | 2,4-Dinitrophenol, also called DNP is a yellow solid with no known smell. It dissolves slightly in water. DNP present in water and soil as a pollutant does not easily evaporate to air. It uncouples oxidative phosphorylation by carrying protons across the mitochondrial membrane, leading to a rapid consumption of energy without generation of ATP. 2,4-DNP was used in the 1930s as a weightreduction drug, but this was discontinued in 1938 because of the many reports of adverse effects in people who used it. (L168, L169) |
| FRCD ID | F03338 |
| CAS Number | 51-28-5 |
| PubChem CID | 1493 |
| Formula | C6H4N2O5 |
| IUPAC Name | None |
| InChI Key | UFBJCMHMOXMLKC-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H |
| Canonical SMILES | C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])O |
| Isomeric SMILES | C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])O |
| Wikipedia | 2,4-Dinitrophenol |
| Synonyms |
alpha-Dinitrophenol
2,4-dinitrophenol
51-28-5
Aldifen
Solfo Black B
Tertrosulphur PBR
Phenol, 2,4-dinitro-
2,4-Dnp
Solfo Black G
1-Hydroxy-2,4-dinitrobenzene
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenols |
| Subclass | Nitrophenols |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Dinitrophenols |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Dinitrophenol - Nitrobenzene - Nitroaromatic compound - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - C-nitro compound - Organic nitro compound - Organic oxoazanium - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as dinitrophenols. These are organic aromatic compounds containing a benzene that carries a single phenol group and exactly two nitro groups. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 184.107 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 0 |
| Complexity | 220 |
| Monoisotopic Mass | 184.012 |
| Exact Mass | 184.012 |
| XLogP | 1.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Uncovering the Molecular Mechanism of Anti-Allergic Activity of SilkwormPupa-Grown Cordyceps militaris Fruit Body. | Am J Chin Med | 2017 | 28367714 |
| Mechanistic Analysis of the Effect of Deamidation on the Immunogenicity of Anthrax Protective Antigen. | Clin Vaccine Immunol | 2016 May | 26912784 |
| Assessment of phenolic herbicide toxicity and mode of action by different assays. | Environ Sci Pollut Res Int | 2016 Apr | 26695414 |
| Body Mass Parameters, Lipid Profiles and Protein Contents of Zebrafish Embryos and Effects of 2,4-Dinitrophenol Exposure. | PLoS One | 2015 | 26292096 |
| Diarylacylhydrazones: Clostridium-selective antibacterials with activity against stationary-phase cells. | Bioorg Med Chem Lett | 2014 Jan 15 | 24360560 |
| Quenching of tryptophan fluorescence in the presence of 2,4-DNP, 2,6-DNP, 2,4-DNA and DNOC and their mechanism of toxicity. | Molecules | 2013 Feb 18 | 23429343 |
| H(+)/phenanthrene symporter and aquaglyceroporin are implicated in phenanthrene uptake by wheat (Triticum aestivum L.) roots. | J Environ Qual | 2012 Jan-Feb | 22218187 |
| Enhancing the performance of sequencing batch reactors by adding crushed date seeds to remove high concentrations of 2,4-dinitrophenol. | Water Environ Res | 2011 Nov | 22195430 |
| Efflux mediated adaptive and cross resistance to ciprofloxacin and benzalkoniumchloride in Pseudomonas aeruginosa of dairy origin. | J Basic Microbiol | 2011 Jun | 21298686 |
| Prenatal zinc supplementation of zinc-adequate rats adversely affects immunity in offspring. | J Nutr | 2011 Aug | 21697297 |
| Accumulation of phenanthrene by roots of intact wheat (Triticum acstivnm L.) seedlings: passive or active uptake? | BMC Plant Biol | 2010 Mar 22 | 20307286 |
| Prenatal developmental toxicity of gavage or feeding doses of 2-sec-butyl-4,6-dinitrophenol in rats. | Reprod Toxicol | 2010 Jun | 20132881 |
| Photocatalytic degradation of 2,4-dinitrophenol. | J Hazard Mater | 2009 May 15 | 18849116 |
| A megalin-like receptor is involved in protein endocytosis in the midgut of an insect (Bombyx mori, Lepidoptera). | Am J Physiol Regul Integr Comp Physiol | 2008 Oct | 18635456 |
| Transport of glucose by Bifidobacterium animalis subsp. lactis occurs viafacilitated diffusion. | Appl Environ Microbiol | 2008 Nov | 18791026 |
| Dinitrophenol and obesity: an early twentieth-century regulatory dilemma. | Regul Toxicol Pharmacol | 2007 Jul | 17475379 |
| Germanium-68 as an adequate tracer for silicon transport in plants.Characterization of silicon uptake in different crop species. | Plant Physiol | 2007 Jan | 17098850 |
| Gut transport of a molybdenum/ascorbic acid complex. | Drugs R D | 2006 | 16542057 |
| Quantitative analysis of cereulide, an emetic toxin of Bacillus cereus, by using rat liver mitochondria. | Microbiol Immunol | 2005 | 15665450 |
| Redox signaling in the growth and development of colonial hydroids. | J Exp Biol | 2003 Feb | 12517982 |
Targets
- General Function:
- Identical protein binding
- Specific Function:
- Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain.
- Gene Name:
- TTR
- Uniprot ID:
- P02766
- Molecular Weight:
- 15886.88 Da
- Mechanism of Action:
- 2,4-Dinitrophenol has been suggested to bind serum proteins such as transthyretin. In fact it was proposed as a therapeutic agent for the prevention/inhibition of amyloid diseases through stabilization of the native fold of transthyretin. (A126,A127)
References
- Morais-de-Sa E, Neto-Silva RM, Pereira PJ, Saraiva MJ, Damas AM: The binding of 2,4-dinitrophenol to wild-type and amyloidogenic transthyretin. Acta Crystallogr D Biol Crystallogr. 2006 May;62(Pt 5):512-9. Epub 2006 Apr 19. [16627944 ]