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MetaCyc Compound: 2,4-dinitrophenol

Synonyms: 1-hydroxy-2,4-dinitrobenzene, 2,4-DNP, α-dinitrophenol

Superclasses: a nitrohydrocarbon a C-nitro compound

Summary:
2,4-Dinitrophenol has been used during the first world war by the French in the manufacture of munitions. Later it was also used as a dye, wood preserver, herbicide and photographic developer.

2,4-Dinitrophenol is a well known protonophore (an uncoupler of oxidative phosphorylation) by preventing the uptake of inorganic phosphate molecules into the mitochondria [Loomis48, Rognstad69, Ilivicky69]. At lower concentrations this property causes a significant increase in the basal metabolic rate, and as aresult, a rapid weight loss, which prompted its use as weight loss drug. However, severe side effects have resulted in its labelling as "extremely dangerous and not fit for human consumption" by the Federal Food, Drug and Cosmetic Act of 1938. The UK Food Standard Agency issued a warning in 2003, labelling it as "not fit for human consumption" as well. Despite this, 2,4-dinitrophenol is still marketed as a weight loss drug, mainly over the internet [Grundlingh11].

It has been reported that at low concentrations 2,4-dinitrophenol protects neurons against β-amyloid toxicity [De06b] and attenuates nitroprusside-induced toxicity [Lozinsky13].

A number of organisms that utilize 2,4-dinitrophenol as the sole source of carbon and nitrogen have been described [Jensen55, Gundersen56, Hess90, Schmidt89a, Simpson53, Lenke92, Behrend99, Ebert99, Ebert01, Walters01].

Chemical Formula: C6H3N2O5

Molecular Weight: 183.1 Daltons

Monoisotopic Molecular Weight: 186.02767131349998 Daltons

2,4-dinitrophenol compound structure

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

InChI: InChI=1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H/p-1

InChIKey: InChIKey=UFBJCMHMOXMLKC-UHFFFAOYSA-M

Unification Links: CAS:51-28-5 , ChEBI:42017 , ChemSpider:146880 , DrugBank:DB04528 , KEGG:C02496 , PubChem:167909

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -97.8587 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

2,4,6-trinitrophenol and 2,4-dinitrophenol degradation :
2,4-dinitrophenol + NADPH → O-[5-(oxidonitroso)-4-oxocyclohex-2-en-1-ylidenenitroso]oxidanidolate + NADP+

Reactions known to produce the compound:

2,4-dinitroanisole degradation :
2,4-dinitroanisole + H2O → 2,4-dinitrophenol + methanol + H+

In Reactions of unknown directionality:

Not in pathways:
2,4-dinitrophenol + NADH = 4-nitrophenol + nitrite + NAD+

Enzymes inhibited by 2,4-dinitrophenol, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: ATP phosphoribosyltransferase [DallLarsen75] , 2-nitrophenol 2-monooxygenase [Zeyer88]

Inhibitor (Mechanism unknown) of: D-lactate dehydrogenase [Schweiger84] , lactyl-CoA dehydratase [Schweiger84, Schweiger85]

Inhibitor (Other types) of: biotin transporter [Prakash74] , tetrathionate decomposing enzyme [Ng00]

Credits:
Revised 21-Jan-2015 by Caspi R , SRI International


References

Behrend99: Behrend C, Heesche-Wagner K (1999). "Formation of hydride-Meisenheimer complexes of picric acid (2,4, 6-trinitrophenol) and 2,4-dinitrophenol during mineralization of picric acid by Nocardioides sp. strain CB 22-2." Appl Environ Microbiol 65(4);1372-7. PMID: 10103224

DallLarsen75: Dall-Larsen T, Fasold H, Klungsoyr L, Kryvi H, Meyer C, Ortanderl F (1975). "Affinity labelling to - SH groups in adenosine - triphosphate - phosphoribosyl transferase with the dinitrophenyl group from S-dinitrophenyl-6-mercaptopurine-riboside 5'-phosphate." Eur J Biochem 60(1);103-7. PMID: 1204631

De06b: De Felice FG, Ferreira ST (2006). "Novel neuroprotective, neuritogenic and anti-amyloidogenic properties of 2,4-dinitrophenol: the gentle face of Janus." IUBMB Life 58(4);185-91. PMID: 16754295

Ebert01: Ebert S, Fischer P, Knackmuss HJ (2001). "Converging catabolism of 2,4,6-trinitrophenol (picric acid) and 2,4-dinitrophenol by Nocardioides simplex FJ2-1A." Biodegradation 12(5);367-76. PMID: 11995829

Ebert99: Ebert S, Rieger PG, Knackmuss HJ (1999). "Function of coenzyme F420 in aerobic catabolism of 2,4, 6-trinitrophenol and 2,4-dinitrophenol by Nocardioides simplex FJ2-1A." J Bacteriol 181(9);2669-74. PMID: 10217752

Grundlingh11: Grundlingh J, Dargan PI, El-Zanfaly M, Wood DM (2011). "2,4-dinitrophenol (DNP): a weight loss agent with significant acute toxicity and risk of death." J Med Toxicol 7(3);205-12. PMID: 21739343

Gundersen56: Gundersen K, Jensen H L (1956). "A Soil Bacterium Decomposing Organic Nitro-Compounds." Acta Agriculturae Scandinavica 6(1);100-114.

Hess90: Hess TF, Schmidt SK, Silverstein J, Howe B (1990). "Supplemental substrate enhancement of 2,4-dinitrophenol mineralization by a bacterial consortium." Appl Environ Microbiol 56(6);1551-8. PMID: 16348203

Ilivicky69: Ilivicky J, Casida JE (1969). "Uncoupling action of 2,4-dinitrophenols, 2-trifluoromethylbenzimidazoles and certain other pesticide chemicals upon mitochondria from different sources and its relation to toxicity." Biochem Pharmacol 18(6);1389-401. PMID: 5799112

Jensen55: Jensen HL, Gundersen K (1955). "Biological decomposition of aromatic nitro-compounds." Nature 175(4451);341. PMID: 13235894

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lenke92: Lenke H, Pieper DH, Bruhn C, Knackmuss HJ (1992). "Degradation of 2,4-dinitrophenol by two Rhodococcus erythropolis strains, HL 24-1 and HL 24-2." Appl Environ Microbiol 58(9);2928-32. PMID: 1444407

Loomis48: Loomis WF, Lipmann F (1948). "Reversible inhibition of the coupling between phosphorylation and oxidation." J Biol Chem 173(2);807. PMID: 18910739

Lozinsky13: Lozinsky OV, Lushchak OV, Storey JM, Storey KB, Lushchak VI (2013). "The mitochondrial uncoupler 2,4-dinitrophenol attenuates sodium nitroprusside-induced toxicity in Drosophila melanogaster: potential involvement of free radicals." Comp Biochem Physiol C Toxicol Pharmacol 158(4);244-52. PMID: 24064327

Ng00: Ng KY, Kamimura K, Sugio T (2000). "Production of hydrogen sulfide from tetrathionate by the iron-oxidizing bacterium Thiobacillus ferrooxidans NASF-1." J Biosci Bioeng 90(2);193-8. PMID: 16232841

Prakash74: Prakash O, Eisenberg MA (1974). "Active transport of biotin in Escherichia coli K-12." J Bacteriol 120(2);785-91. PMID: 4616949

Rognstad69: Rognstad R, Katz J (1969). "The effect of 2,4-dinitrophenol on adipose-tissue metabolism." Biochem J 111(4);431-44. PMID: 4388239

Schmidt89a: Schmidt SK, Gier MJ (1989). "Dynamics of microbial populations in soil: Indigenous microorganisms degrading 2,4-dinitrophenol." Microb Ecol 18(3);285-96. PMID: 24196208

Schweiger84: Schweiger G, Buckel W (1984). "On the dehydration of (R)-lactate in the fermentation of alanine to propionate by Clostridium propionicum." FEBS Lett 1984;171(1);79-84. PMID: 6586495

Schweiger85: Schweiger G, Buckel W (1985). "Identification of acrylate, the product of the dehydration of (R)-lactate catalysed by cell-free extracts from Clostridium propionicum." FEBS Lett 1985;185(2);253-6. PMID: 3996603

Simpson53: Simpson, J.R., Evans, W.C. (1953). "The metabolism of nitrophenols by certain bacteria." Biochem J 55(320th Meeting);xxiv. PMID: 13093710

Walters01: Walters DM, Russ R, Knackmuss HJ, Rouviere PE (2001). "High-density sampling of a bacterial operon using mRNA differential display." Gene 273(2);305-15. PMID: 11595177

Zeyer88: Zeyer J, Kocher HP (1988). "Purification and characterization of a bacterial nitrophenol oxygenase which converts ortho-nitrophenol to catechol and nitrite." J Bacteriol 170(4);1789-94. PMID: 3350791


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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