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 IUPAC 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
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Intestine
  • Liver
  • Placenta
  • Platelet
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableCommentNormal
  • Not Applicable
UrineDetected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
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)Not Available
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

Gene Name:
PON3
Uniprot ID:
Q15166
Reactions
Parathion + Water unknown Diethylthiophosphate + 4-Nitrophenoldetails
Paraoxon + Water unknown Diethylphosphate + 4-Nitrophenoldetails
Gene Name:
ALPP
Uniprot ID:
P05187
Reactions
4-Nitrophenyl phosphate + Water unknown 4-Nitrophenol + Phosphoric aciddetails
Gene Name:
PON1
Uniprot ID:
P27169
Reactions
Parathion + Water unknown Diethylthiophosphate + 4-Nitrophenoldetails
Paraoxon + Water unknown Diethylphosphate + 4-Nitrophenoldetails
Gene Name:
PON2
Uniprot ID:
Q15165
Reactions
Parathion + Water unknown Diethylthiophosphate + 4-Nitrophenoldetails
Paraoxon + Water unknown Diethylphosphate + 4-Nitrophenoldetails
Gene Name:
ALPI
Uniprot ID:
P09923
Reactions
4-Nitrophenyl phosphate + Water unknown 4-Nitrophenol + Phosphoric aciddetails
Gene Name:
ALPL
Uniprot ID:
P05186
Reactions
4-Nitrophenyl phosphate + Water unknown 4-Nitrophenol + Phosphoric aciddetails
Gene Name:
ACPP
Uniprot ID:
P15309
Gene Name:
ALPPL2
Uniprot ID:
P10696
Reactions
4-Nitrophenyl phosphate + Water unknown 4-Nitrophenol + Phosphoric aciddetails
Gene Name:
CYP2E1
Uniprot ID:
P05181
Reactions
4-Nitrophenol + NADPH + Oxygen unknown 4-Nitrocatechol + NADP + Waterdetails
Gene Name:
ACPT
Uniprot ID:
Q9BZG2