Record Information
Version2.0
Creation Date2012-05-31 13:48:03 -0600
Update Date2015-09-13 12:56:10 -0600
Secondary Accession Numbers
  • ECMDB01232
Identification
Name:4-Nitrophenol
Description:4-Nitrophenol, also called p-nitrophenol or 4-hydroxynitrobenzene, is a phenolic compound that has a nitro group at the opposite position of hydroxy group on the benzene ring. (Wikipedia)
Structure
Thumb
Synonyms:
  • 1-Hydroxy-4-nitrobenzene
  • 4-Hydroxynitrobenzene
  • 4-Nitrophenol
  • p-nitrophenol
  • Mononitrophenol
  • Niphen
  • P-Hydroxynitrobenzene
  • P-Nitrophenol
  • Paranitrophenol
  • PNP
Chemical Formula:C6H5NO3
Weight:Average: 139.1088
Monoisotopic: 139.026943031
InChI Key:BTJIUGUIPKRLHP-UHFFFAOYSA-N
InChI:InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H
CAS number:100-02-7
IUPAC Name:4-nitrophenol
Traditional IUPAC Name:P-nitrophenol
SMILES:OC1=CC=C(C=C1)[N+]([O-])=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitrophenols. These are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassNitrophenols
Direct ParentNitrophenols
Alternative Parents
Substituents
  • Nitrophenol
  • Nitrobenzene
  • Nitroaromatic compound
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:113.8 °C
Experimental Properties:
PropertyValueSource
Water Solubility:11.6 mg/mL [SCHWARZENBACH,RP et al.(1988)]PhysProp
LogP:1.91 [HANSCH,C ET AL. (1995)]PhysProp
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 Area66.05 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.36 m³·mol⁻¹ChemAxon
Polarizability12.18 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Aminobenzoate DegradationPW000757 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • 1,4-Dichlorobenzene degradation ec00627
  • Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9200000000-6a367c2627bf30cad163View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00or-9500000000-a23a22fc322241325904View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9400000000-670d24ff2b2b121a7ab8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9400000000-b5aea5436a88b29179e9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05n0-9300000000-f284a324180bf4d7ffc2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2009127011-85632179856636169d28View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6t-1900000000-70af7d7902cd35a26f29View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9200000000-6a367c2627bf30cad163View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00or-9500000000-a23a22fc322241325904View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9400000000-670d24ff2b2b121a7ab8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9400000000-b5aea5436a88b29179e9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05n0-9300000000-f284a324180bf4d7ffc2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2009127011-85632179856636169d28View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6t-1900000000-70af7d7902cd35a26f29View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9200000000-6a367c2627bf30cad163View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00or-9500000000-a23a22fc322241325904View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9400000000-670d24ff2b2b121a7ab8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9400000000-b5aea5436a88b29179e9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05n0-9300000000-f284a324180bf4d7ffc2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2009127011-85632179856636169d28View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6t-1900000000-70af7d7902cd35a26f29View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9200000000-6a367c2627bf30cad163View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00or-9500000000-a23a22fc322241325904View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-7900000000-d4915e2347113b56d32cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9800000000-7bde61a3b7f0a23ddd41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-00dl-0900000000-653240f82298b3880e70View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-014l-9100000000-1dd6a69ee33aeb4207a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-014r-9000000000-397a0913b382e58ae418View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-00kr-9200000000-039471e02c3307757a0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-00or-9500000000-a23a22fc322241325904View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-000i-9400000000-12717928037244536b6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-000i-9400000000-f133ed564f0a12bd3871View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-05n0-9300000000-d39a8dbf21962717a2eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-9200000000-bff0a2a3c15629cc6ec2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052r-0900000000-1279a141e229fec8dbd4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-052r-0900000000-1279a141e229fec8dbd4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-9200000000-bff0a2a3c15629cc6ec2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-d01a64d09fb568b883b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-58e0d9a2ff9a60a8c4f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-2900000000-fbf4f5da283a46ec8ed8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-3c17676b62ba6a9be8d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-4dcec4bcef5be284e738View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-3900000000-de3f2773a5601a2eec1bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00kr-9300000000-d76f14df8da868057d44View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Leng G, Lewalter J: Role of individual susceptibility in risk assessment of pesticides. Occup Environ Med. 1999 Jul;56(7):449-53. Pubmed: 10472315
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • 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
Synthesis Reference:Fache, Eric; Righini, Sebastien. Preparation of a nitrophenol. Fr. Demande (2004), 35 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16836
HMDB IDHMDB01232
Pubchem Compound ID980
Kegg IDC00870
ChemSpider ID955
Wikipedia4-Nitrophenol
BioCyc IDP-NITROPHENOL
EcoCyc IDP-NITROPHENOL
Ligand ExpoNPO

Enzymes

General function:
Involved in catalytic activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
phoA
Uniprot ID:
P00634
Molecular weight:
49438
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate.
General function:
Involved in acid phosphatase activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
appA
Uniprot ID:
P07102
Molecular weight:
47056
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate.
Myo-inositol hexakisphosphate + H(2)O = 1D-myo-inositol 1,2,3,5,6-pentakisphosphate + phosphate.
General function:
Involved in acid phosphatase activity
Specific function:
Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
Gene Name:
aphA
Uniprot ID:
P0AE22
Molecular weight:
26103
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate.