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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:30:52 UTC
HMDB IDHMDB01232
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Nitrophenol
Description4-Nitrophenol is a phenolic metabolite of environmental chemicals present in samples from the general population. 4-Nitrophenol measurement in urine is used in biological monitoring for establishing the presence and magnitude of exposures to pesticides. (PMID 15899376 ) (Methods in Biotechnology, 2006,61-78).
Structure
Thumb
Synonyms
  1. Mononitrophenol
  2. p-Hydroxynitrobenzene
  3. 1-Hydroxy-4-nitrobenzene
  4. 4-Hydroxynitrobenzene
  5. 4-Nitrophenol
  6. Niphen
  7. p-Nitrophenol
  8. Paranitrophenol
Chemical FormulaC6H5NO3
Average Molecular Weight139.1088
Monoisotopic Molecular Weight139.026943031
IUPAC Name4-nitrophenol
Traditional NameP-nitrophenol
CAS Registry Number100-02-7
SMILES
OC1=CC=C(C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H
InChI KeyBTJIUGUIPKRLHP-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenols and Derivatives
Sub ClassNitrophenols and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Nitrobenzenes
  • mononitrophenol(ChEBI)
Substituents
  • Aminophenol Derivative
  • Nitro Compound
  • Organic Oxoazanium
Direct ParentNitrophenols and Derivatives
Ontology
StatusDetected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point113.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.6 mg/mLNot Available
LogP1.91HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility3.6 g/LALOGPS
logP1.93ALOGPS
logP1.61ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)7.04ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.05ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.36ChemAxon
Polarizability12.18ChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Intestine
  • Liver
  • Placenta
  • Platelet
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022503
KNApSAcK IDNot Available
Chemspider ID955
KEGG Compound IDC00870
BioCyc IDP-NITROPHENOL
BiGG ID36247
Wikipedia Link4-Nitrophenol
NuGOwiki LinkHMDB01232
Metagene LinkHMDB01232
METLIN ID4100
PubChem Compound980
PDB IDNPO
ChEBI ID16836
References
Synthesis ReferenceFache, Eric; Righini, Sebastien. Preparation of a nitrophenol. Fr. Demande (2004), 35 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ozawa S, Shimizu M, Katoh T, Miyajima A, Ohno Y, Matsumoto Y, Fukuoka M, Tang YM, Lang NP, Kadlubar FF: Sulfating-activity and stability of cDNA-expressed allozymes of human phenol sulfotransferase, ST1A3*1 ((213)Arg) and ST1A3*2 ((213)His), both of which exist in Japanese as well as Caucasians. J Biochem (Tokyo). 1999 Aug;126(2):271-7. Pubmed: 10423517
  2. Sharaev PN, Gabdrakhmanova NK, Strelkova TN, Sakhabutdinova EP: [Detection of N-acetyl-beta-D-hexosaminidase in urine] Klin Lab Diagn. 2004 May;(5):40-2. Pubmed: 15230116
  3. Anderson RJ, Garcia MJ, Liebentritt DK, Kay HD: Localization of human blood phenol sulfotransferase activities: novel detection of the thermostable enzyme in granulocytes. J Lab Clin Med. 1991 Nov;118(5):500-9. Pubmed: 1940590
  4. Kayamori Y, Katayama Y: Enzymatic method for assaying calcium in serum and urine with porcine pancreatic alpha-amylase. Clin Chem. 1994 May;40(5):781-4. Pubmed: 8174252
  5. Pacifici GM, Temellini A, Castiglioni M, D'Alessandro C, Ducci A, Giuliani L: Interindividual variability of the human hepatic sulphotransferases. Chem Biol Interact. 1994 Jun;92(1-3):219-31. Pubmed: 8033255
  6. Bowers GN Jr, McComb RB, Christensen RG, Schaffer R: High-purity 4-nitrophenol: purification, characterization, and specifications for use as a spectrophotometric reference material. Clin Chem. 1980 May;26(6):724-9. Pubmed: 7371150
  7. Bellavite P, Andrioli G, Guzzo P, Arigliano P, Chirumbolo S, Manzato F, Santonastaso C: A colorimetric method for the measurement of platelet adhesion in microtiter plates. Anal Biochem. 1994 Feb 1;216(2):444-50. Pubmed: 8179202
  8. Pacifici GM: Sulfation of drugs and hormones in mid-gestation human fetus. Early Hum Dev. 2005 Jul;81(7):573-81. Epub 2004 Dec 8. Pubmed: 16009282
  9. Vitarius JA, Sultatos LG: Kinetic mechanism of the detoxification of the organophosphate paraoxon by human serum A-esterase. Drug Metab Dispos. 1994 May-Jun;22(3):472-8. Pubmed: 8070326
  10. Pacifici GM, Marchi G: Interindividual variability of phenol- and catechol-sulphotransferases in platelets from adults and newborns. Br J Clin Pharmacol. 1993 Dec;36(6):593-7. Pubmed: 12959278
  11. Osnes T, Sandstad O, Skar V, Osnes M: beta-Glucuronidase in common duct bile, methodological aspects, variation of pH optima and relation to gallstones. Scand J Clin Lab Invest. 1997 Jul;57(4):307-15. Pubmed: 9249878
  12. Young WF Jr, Okazaki H, Laws ER Jr, Weinshilboum RM: Human brain phenol sulfotransferase: biochemical properties and regional localization. J Neurochem. 1984 Sep;43(3):706-15. Pubmed: 6589361
  13. Leng G, Lewalter J: Role of individual susceptibility in risk assessment of pesticides. Occup Environ Med. 1999 Jul;56(7):449-53. Pubmed: 10472315
  14. Belanger G, Beaulieu M, Levesque E, Hum DW, Belanger A: Expression and characterization of a novel UDP-glucuronosyltransferase, UGT2B9, from cynomolgus monkey. DNA Cell Biol. 1997 Oct;16(10):1195-205. Pubmed: 9364930
  15. Birk AV, Broekman MJ, Gladek EM, Robertson HD, Drosopoulos JH, Marcus AJ, Szeto HH: Role of extracellular ATP metabolism in regulation of platelet reactivity. J Lab Clin Med. 2002 Sep;140(3):166-75. Pubmed: 12271274
  16. Rossi AM, Maggini V, Fredianelli E, Di Bello D, Pietrabissa A, Mosca F, Barale R, Pacifici GM: Phenotype-genotype relationships of SULT1A1 in human liver and variations in the IC50 of the SULT1A1 inhibitor quercetin. Int J Clin Pharmacol Ther. 2004 Oct;42(10):561-7. Pubmed: 15516026
  17. Reiter C, Mwaluko G, Dunnette J, Van Loon J, Weinshilboum R: Thermolabile and thermostable human platelet phenol sulfotransferase. Substrate specificity and physical separation. Naunyn Schmiedebergs Arch Pharmacol. 1983 Sep;324(2):140-7. Pubmed: 6139755
  18. Bravo R, Caltabiano LM, Fernandez C, Smith KD, Gallegos M, Whitehead RD Jr, Weerasekera G, Restrepo P, Bishop AM, Perez JJ, Needham LL, Barr DB: Quantification of phenolic metabolites of environmental chemicals in human urine using gas chromatography-tandem mass spectrometry and isotope dilution quantification. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jun 25;820(2):229-36. Epub 2005 Apr 26. Pubmed: 15899376

Enzymes

General function:
Involved in arylesterase activity
Specific function:
Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:
PON3
Uniprot ID:
Q15166
Molecular weight:
39607.185
Reactions
Parathion + Water → Diethylthiophosphate + 4-Nitrophenoldetails
Paraoxon + Water → Diethylphosphate + 4-Nitrophenoldetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPP
Uniprot ID:
P05187
Molecular weight:
57953.31
Reactions
4-Nitrophenyl phosphate + Water → 4-Nitrophenol + Phosphoric aciddetails
General function:
Involved in arylesterase activity
Specific function:
Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:
PON1
Uniprot ID:
P27169
Molecular weight:
39730.99
Reactions
Parathion + Water → Diethylthiophosphate + 4-Nitrophenoldetails
Paraoxon + Water → Diethylphosphate + 4-Nitrophenoldetails
General function:
Involved in arylesterase activity
Specific function:
Capable of hydrolyzing lactones and a number of aromatic carboxylic acid esters. Has antioxidant activity. Is not associated with high density lipoprotein. Prevents LDL lipid peroxidation, reverses the oxidation of mildly oxidized LDL, and inhibits the ability of MM-LDL to induce monocyte chemotaxis.
Gene Name:
PON2
Uniprot ID:
Q15165
Molecular weight:
39380.535
Reactions
Parathion + Water → Diethylthiophosphate + 4-Nitrophenoldetails
Paraoxon + Water → Diethylphosphate + 4-Nitrophenoldetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPI
Uniprot ID:
P09923
Molecular weight:
56811.695
Reactions
4-Nitrophenyl phosphate + Water → 4-Nitrophenol + Phosphoric aciddetails
General function:
Involved in catalytic activity
Specific function:
This isozyme may play a role in skeletal mineralization.
Gene Name:
ALPL
Uniprot ID:
P05186
Molecular weight:
57304.435
Reactions
4-Nitrophenyl phosphate + Water → 4-Nitrophenol + Phosphoric aciddetails
General function:
Involved in hydrolase activity
Specific function:
Involved in osteopontin/bone sialoprotein dephosphorylation. Its expression seems to increase in certain pathological states such as Gaucher and Hodgkin diseases, the hairy cell, the B-cell, and the T-cell leukemias.
Gene Name:
ACP5
Uniprot ID:
P13686
Molecular weight:
36598.47
General function:
Involved in acid phosphatase activity
Specific function:
A non-specific tyrosine phosphatase that dephosphorylates a diverse number of substrates under acidic conditions (pH 4-6) including alkyl, aryl, and acyl orthophosphate monoesters and phosphorylated proteins. Has lipid phosphatase activity and inactivates lysophosphatidic acid in seminal plasma. Isoform 2: the cellular form also has ecto-5'-nucleotidase activity in dorsal root ganglion (DRG) neurons. Generates adenosine from AMP which acts as a pain suppressor. Acts as a tumor suppressor of prostate cancer through dephosphorylation of ERBB2 and deactivation of MAPK-mediated signaling.
Gene Name:
ACPP
Uniprot ID:
P15309
Molecular weight:
44565.715
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPPL2
Uniprot ID:
P10696
Molecular weight:
57376.515
Reactions
4-Nitrophenyl phosphate + Water → 4-Nitrophenol + Phosphoric aciddetails
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
Reactions
4-Nitrophenol + NADPH + Oxygen → 4-Nitrocatechol + NADP + Waterdetails
General function:
Involved in acid phosphatase activity
Specific function:
Hydrolyzes lysophosphatidic acid to monoacylglycerol.
Gene Name:
ACP6
Uniprot ID:
Q9NPH0
Molecular weight:
48853.955
General function:
Involved in acid phosphatase activity
Specific function:
Dephosphorylates receptor tyrosine-protein kinase erbB-4 and inhibits the ligand-induced proteolytic cleavage.
Gene Name:
ACPT
Uniprot ID:
Q9BZG2
Molecular weight:
46089.015
General function:
Involved in protein tyrosine phosphatase activity
Specific function:
Not Available
Gene Name:
ACP1
Uniprot ID:
B5MCC7
Molecular weight:
12230.0