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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 [Zhang12f]. 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, Zhang09c] 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

4-nitrophenol compound structure

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+
p-nitrophenyl-α-L-rhamnopyranoside + H2O → 4-nitrophenol + β-L-rhamnopyranose + H+

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

Not in pathways:
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

This compound has been characterized as an alternative substrate of the following enzymes: dopamine sulfotransferase

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

Zhang09c: 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

Zhang12f: 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 SRI International Pathway Tools version 19.0 on Tue Mar 31, 2015, BIOCYC13B.