MetaCyc Pathway: paraoxon degradation
Inferred from experiment

Pathway diagram: paraoxon degradation

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: Degradation/Utilization/AssimilationAromatic Compounds Degradation

Some taxa known to possess this pathway include : Sphingobium fuliginis

Expected Taxonomic Range: Bacteria

General Background

Organophosphate pesticides such as parathion and methyl parathion have been used extensively as insecticides, fungicides, and herbicides. These compounds, being potent cholinesterase inhibitors (see EC and for cholinesterases), are extremely toxic to most animals including humans (in which LD50 is 5 to 10 mg/kg), and may cause death by inducing respiratory failure. Under aerobic conditions, parathion is activated by oxidative desulfuration to the oxygen analog paraoxon [Spencer80], which has a potent anticholinesterase effect and is more toxic than the parent chemical [Guilhermino96].

About This Pathway

The enzymes of the aryldialkylphosphatase family (EC generally have broad substrate specificity, and are capable of accepting many different organophosphate substrates. For more information about this pathway, please see parathion degradation, as the same enzymes catalyze the degradation of paraoxon.

It should be mentioned that the Keasling lab has constructed a genetically engineered Pseudomonas putida strain that can fully mineralize paraoxon [delaPena06]. This organism contains the Sphingobium fuliginis opd gene encoding organophosphate acid anhydrase, the Pseudomonas sp. ENV2030 genes encoding the degradation of 4-nitrophenol (see 4-nitrophenol degradation I), the Delftia acidovorans pdeA gene encoding diethylphosphate phosphodiesterase, and a constitutively expressed phoA gene from Pseudomonas aeruginosa, encoding alkaline phosphatase.

Created 28-Feb-2007 by Caspi R, SRI International


delaPena06: de la Pena Mattozzi M, Tehara SK, Hong T, Keasling JD (2006). "Mineralization of paraoxon and its use as a sole C and P source by a rationally designed catabolic pathway in Pseudomonas putida." Appl Environ Microbiol 72(10);6699-706. PMID: 17021221

Guilhermino96: Guilhermino L, Celeste Lopes M, Carvalho AP, Soares AM (1996). "Inhibition of acetylcholinesterase activity as effect criterion in acute tests with juvenile Daphnia magna." Chemosphere 32(4);727-38. PMID: 8867149

Spencer80: Spencer, W.F., Adams, J.D., Shoup, T.D., Spear, R.C. (1980). "Conversion of Parathion to Paraoxon on Soil Dusts and Clay Minerals as Affected by Ozone and UV Light." J. Agric. Food Chem. 28: 366-371.

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Bondarenko04: Bondarenko S, Gan J, Haver DL, Kabashima JN (2004). "Persistence of selected organophosphate and carbamate insecticides in waters from a coastal watershed." Environ Toxicol Chem 23(11);2649-54. PMID: 15559280

Harper88: Harper LL, McDaniel CS, Miller CE, Wild JR (1988). "Dissimilar plasmids isolated from Pseudomonas diminuta MG and a Flavobacterium sp. (ATCC 27551) contain identical opd genes." Appl Environ Microbiol 54(10);2586-9. PMID: 3202637

Keil89: Keil TU (1989). "[AIDS fungus infections. Fluconazole--a new preparation in development]." Fortschr Med 107(10);69-70. PMID: 2541058

Khajamohiddin06: Khajamohiddin S, Babu PS, Chakka D, Merrick M, Bhaduri A, Sowdhamini R, Siddavattam D (2006). "A novel meta-cleavage product hydrolase from Flavobacterium sp. ATCC27551." Biochem Biophys Res Commun 351(3);675-81. PMID: 17078928

Kitagawa04: Kitagawa W, Kimura N, Kamagata Y (2004). "A novel p-nitrophenol degradation gene cluster from a gram-positive bacterium, Rhodococcus opacus SAO101." J Bacteriol 186(15);4894-902. PMID: 15262926

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

Mulbry86: Mulbry WW, Karns JS, Kearney PC, Nelson JO, McDaniel CS, Wild JR (1986). "Identification of a plasmid-borne parathion hydrolase gene from Flavobacterium sp. by southern hybridization with opd from Pseudomonas diminuta." Appl Environ Microbiol 51(5);926-30. PMID: 3015022

Mulbry89: Mulbry WW, Karns JS (1989). "Purification and characterization of three parathion hydrolases from gram-negative bacterial strains." Appl Environ Microbiol 55(2);289-93. PMID: 2541658

Perry07: Perry LL, Zylstra GJ (2007). "Cloning of a gene cluster involved in the catabolism of p-nitrophenol by Arthrobacter sp. strain JS443 and characterization of the p-nitrophenol monooxygenase." J Bacteriol 189(21);7563-72. PMID: 17720792

Sethunathan73: Sethunathan N, Yoshida T (1973). "A Flavobacterium sp. that degrades diazinon and parathion." Can J Microbiol 19(7);873-5. PMID: 4727806

Siddavattam03: Siddavattam D, Khajamohiddin S, Manavathi B, Pakala SB, Merrick M (2003). "Transposon-like organization of the plasmid-borne organophosphate degradation (opd) gene cluster found in Flavobacterium sp." Appl Environ Microbiol 69(5);2533-9. PMID: 12732518

Spain91: Spain JC, Gibson DT (1991). "Pathway for Biodegradation of p-Nitrophenol in a Moraxella sp." Appl Environ Microbiol 57(3);812-819. PMID: 16348446

Zhang09: Zhang JJ, Liu H, Xiao Y, Zhang XE, Zhou NY (2009). "Identification and characterization of catabolic para-nitrophenol 4-monooxygenase and para-benzoquinone reductase from Pseudomonas sp. strain WBC-3." J Bacteriol 191(8);2703-10. PMID: 19218392

Zhang12a: Zhang S, Sun W, Xu L, Zheng X, Chu X, Tian J, Wu N, Fan Y (2012). "Identification of the para-nitrophenol catabolic pathway, and characterization of three enzymes involved in the hydroquinone pathway, in pseudomonas sp. 1-7." BMC Microbiol 12;27. PMID: 22380602

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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
Page generated by Pathway Tools version 20.0 (software by SRI International) on Fri May 6, 2016, BIOCYC13A.