4-Nitrophenol (YMDB00316)

Identification
YMDB IDYMDB00316
Name4-Nitrophenol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4-Nitrophenol, also known as niphen or PNP, belongs to the class of organic compounds known as nitrophenols. Nitrophenols 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. 4-Nitrophenol is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Nitrophenol exists in all living species, ranging from bacteria to humans. 4-Nitrophenol is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-Hydroxy-4-nitrobenzene
  • 4-Hydroxynitrobenzene
  • 4-Nitrophenol
  • Mononitrophenol
  • Niphen
  • p-Hydroxynitrobenzene
  • p-Nitrophenol
  • Paranitrophenol
  • PNP
  • 4-Nitrophenol, (18)O-labeled CPD
  • 4-Nitrophenol, 1-(13)C-labeled CPD
  • 4-Nitrophenol, manganese (2+) salt
  • 4-Nitrophenol, silver(2+) salt
  • 4-Nitrophenol, sodium salt, (2:1), dihydrate
  • 4-Nitrophenol, tin (4+) salt
  • 4-Nitrophenol, 2,6-(13)C2-labeled CPD
  • 4-Nitrophenol, 2-(14)C-labeled CPD
  • 4-Nitrophenol, copper(1+) salt
  • 4-Nitrophenol, potassium salt
  • 4-Nitrophenol, tin (2+) salt
  • 4-Nitrophenol, 14C-labeled CPD
  • 4-Nitrophenol, ammonium salt
  • 4-Nitrophenol, ion(1-)
  • 4-Nitrophenol, ion(1-) hydride
  • 4-Nitrophenol, sodium salt
  • 4-Nitrophenol, 2,6-(14)C2-labeled CPD
  • 4-Nitrophenol, aluminum salt
  • 4-Nitrophenol, cesium salt
  • 4-Nitrophenol, iron(3+) salt
  • 4-Nitrophenol, lithium salt
  • 4-Nitrophenol, manganese salt
  • 4-Nitrophenol, zinc salt
  • 4-Hydroxy-1-nitrobenzene
  • 4-Nitrophenolate
CAS number100-02-7
WeightAverage: 139.1088
Monoisotopic: 139.026943031
InChI KeyBTJIUGUIPKRLHP-UHFFFAOYSA-N
InChIInChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H
IUPAC Name4-nitrophenol
Traditional IUPAC NameP-nitrophenol
Chemical FormulaC6H5NO3
SMILES[H]OC1=C([H])C([H])=C(C([H])=C1[H])[N+]([O-])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrophenols. Nitrophenols 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
StateSolid
Charge0
Melting point113.8 °C
Experimental Properties
PropertyValueReference
Water Solubility11.6 mg/mL at 20 oC [SCHWARZENBACH,RP et al. (1988)]PhysProp
LogP1.91 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.6 g/LALOGPS
logP1.93ALOGPS
logP1.61ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)7.07ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.36 m³·mol⁻¹ChemAxon
Polarizability12.22 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9200000000-6a367c2627bf30cad163JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00or-9500000000-a23a22fc322241325904JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9400000000-670d24ff2b2b121a7ab8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9400000000-b5aea5436a88b29179e9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05n0-9300000000-f284a324180bf4d7ffc2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2009127011-85632179856636169d28JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6t-1900000000-70af7d7902cd35a26f29JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9200000000-6a367c2627bf30cad163JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00or-9500000000-a23a22fc322241325904JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9400000000-670d24ff2b2b121a7ab8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9400000000-b5aea5436a88b29179e9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05n0-9300000000-f284a324180bf4d7ffc2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2009127011-85632179856636169d28JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6t-1900000000-70af7d7902cd35a26f29JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9200000000-6a367c2627bf30cad163JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00or-9500000000-a23a22fc322241325904JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9400000000-670d24ff2b2b121a7ab8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9400000000-b5aea5436a88b29179e9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05n0-9300000000-f284a324180bf4d7ffc2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2009127011-85632179856636169d28JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6t-1900000000-70af7d7902cd35a26f29JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-9200000000-6a367c2627bf30cad163JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00or-9500000000-a23a22fc322241325904JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-7900000000-d4915e2347113b56d32cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9800000000-7bde61a3b7f0a23ddd41JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-00dl-0900000000-653240f82298b3880e70JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-014l-9100000000-1dd6a69ee33aeb4207a3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-014r-9000000000-397a0913b382e58ae418JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-00kr-9200000000-039471e02c3307757a0cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-00or-9500000000-a23a22fc322241325904JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-000i-9400000000-12717928037244536b6bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-000i-9400000000-f133ed564f0a12bd3871JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-05n0-9300000000-d39a8dbf21962717a2eeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-9200000000-bff0a2a3c15629cc6ec2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052r-0900000000-1279a141e229fec8dbd4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-052r-0900000000-1279a141e229fec8dbd4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-9200000000-bff0a2a3c15629cc6ec2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00r6-9300000000-5cb2a9e8e318ca2474fdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-0c7b180f083127156f27JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0a4i-0900000000-c41839802d48c97c72b7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0a4i-0900000000-465b86a7fa9c91aea091JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-052r-0900000000-7545ed558dcbc5a7a386JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-052r-0900000000-24c57afe8ccf403e589bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4r-2900000000-396ebc9986624989747eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-d01a64d09fb568b883b1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-58e0d9a2ff9a60a8c4f6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-2900000000-fbf4f5da283a46ec8ed8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-3c17676b62ba6a9be8d5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-4dcec4bcef5be284e738JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-3900000000-de3f2773a5601a2eec1bJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00kr-9300000000-d76f14df8da868057d44JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Fache, Eric; Righini, Sebastien. Preparation of a nitrophenol. Fr. Demande (2004), 35 pp.
External Links:
ResourceLink
CHEBI ID16836
HMDB IDHMDB01232
Pubchem Compound ID980
Kegg IDC00870
ChemSpider ID955
FOODB IDFDB022503
Wikipedia4-Nitrophenol
BioCyc IDP-NITROPHENOL

Enzymes

Protein Details
1. 4-nitrophenylphosphatase
General function:
Involved in catalytic activity
Specific function:
PHO13 is dispensable for vegetative growth and sporulation
Gene Name:
PHO13
Uniprot ID:
P19881
Molecular weight:
34624.30078
Reactions
4-nitrophenyl phosphate + H(2)O → 4-nitrophenol + phosphate.