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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: 4-nitrophenol

Synonyms: p-nitrophenol, PNP, niphen, 4-hydroxynitrobenzene, para-nitrophenol

Superclasses: a nitrohydrocarbon a C-nitro compound
an aromatic compound a phenol

Summary:
4-Nitrophenol is a common environmental pollutant owing to its wide application in pharmaceuticals, explosives, dyes and agrochemicals [Zhang12b]. It also accumulates in the soil due to the hydrolysis of organophosphorus insecticides such as parathion or methyl parathion [Bondarenko04]. Although PNP is less toxic than MP, it is also considered a significant potential toxic contaminant [Spain91, Zhang09e] and belongs to one of 275 hazardous substances commonly found at Superfund sites [Perry07, Kitagawa04].

Chemical Formula: C6H4NO3

Molecular Weight: 138.1 Daltons

Monoisotopic Molecular Weight: 140.0347680641 Daltons

SMILES: C1(C=C([O-])C=CC=1[N+](=O)[O-])

InChI: InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H/p-1

InChIKey: InChIKey=BTJIUGUIPKRLHP-UHFFFAOYSA-M

Unification Links: CAS:100-02-7 , ChEBI:57917 , ChemSpider:559254 , HMDB:HMDB01232 , KEGG:C00870 , MetaboLights:MTBLC57917 , PubChem:644235

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -24.007578 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

4-nitrophenol degradation I :
4-nitrophenol + NAD(P)H + oxygen + H+ → 1,4-benzoquinone + nitrite + NAD(P)+ + H2O

4-nitrophenol degradation II :
4-nitrophenol + NADH + oxygen + 2 H+ → 4-nitrocatechol + NAD+ + H2O

Not in pathways:
4-nitrophenol + NADPH + oxygen + 2 H+ → 4-nitrocatechol + NADP+ + H2O

Reactions known to produce the compound:

methyl parathion degradation :
methyl parathion + H2O → 4-nitrophenol + dimethylthiophosphate + 2 H+

paraoxon degradation :
paraoxon + H2O → diethylphosphate + 4-nitrophenol + 2 H+

parathion degradation :
parathion + H2O → diethylthiophosphate + 4-nitrophenol + 2 H+

Not in pathways:
4-nitrophenyl phosphate[periplasmic space] + H2O[periplasmic space]4-nitrophenol[periplasmic space] + phosphate[periplasmic space] + H+[periplasmic space]
p-nitrophenyl-α-D-glucuronide + H2O → D-glucopyranuronate + 4-nitrophenol + H+


an aryl dialkyl phosphate + H2O → a dialkyl phosphate + a phenol
a phenyl acetate + H2O → a phenol + acetate + H+
a phenol sulfate + H2O ↔ a phenol + sulfate + H+

In Reactions of unknown directionality:

Not in pathways:
bis(p-nitrophenyl) phosphate + H2O = 4-nitrophenyl phosphate + 4-nitrophenol + 2 H+
a p-nitrophenyl 5'-nucleotide + H2O = a nucleoside 5'-monophosphate + 4-nitrophenol + 2 H+
p-nitrophenyl-β-D-glucopyranoside + H2O = 4-nitrophenol + D-glucopyranose + H+


a phenol + NADP+ = an aryl aldehyde + NADPH + H+
3'-phosphoadenylyl-sulfate + a phenol = adenosine 3',5'-bisphosphate + an aryl sulfate
a phenol + NAD+ = an aryl aldehyde + NADH + H+
UDP-α-D-glucose + a phenol = UDP + an aryl β-D-glucoside + H+
a phenol + an aryl sulfate = an aryl sulfate + a phenol

Credits:
Revised 29-May-2012 by Caspi R , SRI International


References

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

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."

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

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

Zhang09e: 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

Zhang12b: 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


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 Nov 27, 2014, biocyc11.