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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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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

Chemical Formula: C6H3N2O5

Molecular Weight: 183.1 Daltons

Monoisotopic Molecular Weight: 186.02767131349998 Daltons

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]

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]


References

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

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

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

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

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Thu Dec 18, 2014, BIOCYC14A.