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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 11:49:22 UTC
Update Date2020-02-26 21:26:26 UTC
HMDB IDHMDB0006492
Secondary Accession Numbers
  • HMDB06492
Metabolite Identification
Common Name4-Nitrophenyl sulfate
Description4-Nitrophenyl sulfate is a minor metabolic byproduct of parathion metabolism that is excreted in the urine (PMID: 1956875 ). Parathion is an organophosphate compound developed in the 1940's. It is a potent insecticide and acaricide. It is highly toxic to non-target organisms, including humans. 4-Nitrophenyl sulfate is also used as a model substrate to investigate the influence of drug therapy, disease, nutrient deficiencies and other physiologically altered conditions on conjugative drug metabolism in animal studies.(PMID: 16844228 ).
Structure
Data?1582752386
Synonyms
ValueSource
p-Nitrophenol sulfateChEBI
p-Nitrophenyl sulfateChEBI
Para-nitrophenyl sulfateChEBI
Sulfuric acid mono(4-nitrophenyl) esterChEBI
p-Nitrophenol sulfuric acidGenerator
p-Nitrophenol sulphateGenerator
p-Nitrophenol sulphuric acidGenerator
p-Nitrophenyl sulfuric acidGenerator
p-Nitrophenyl sulphateGenerator
p-Nitrophenyl sulphuric acidGenerator
Para-nitrophenyl sulfuric acidGenerator
Para-nitrophenyl sulphateGenerator
Para-nitrophenyl sulphuric acidGenerator
Sulfate mono(4-nitrophenyl) esterGenerator
Sulphate mono(4-nitrophenyl) esterGenerator
Sulphuric acid mono(4-nitrophenyl) esterGenerator
4-Nitrophenyl sulfuric acidGenerator
4-Nitrophenyl sulphateGenerator
4-Nitrophenyl sulphuric acidGenerator
4-Nitrophenyl sulfate, ion (1-)MeSH
4-Nitrophenyl sulfate, potassium saltMeSH
4-Nitrophenyl sulfate, sodium saltMeSH
4-NitrophenylHMDB
mono (4-Nitrophenyl)-sulfateHMDB
mono (4-Nitrophenyl)-sulphateHMDB
P-nitro-PhenolHMDB
4-Nitrophenyl sulfateChEBI
4-Nitrophenyl hydrogen sulfuric acidGenerator, HMDB
4-Nitrophenyl hydrogen sulphateGenerator, HMDB
4-Nitrophenyl hydrogen sulphuric acidGenerator, HMDB
Chemical FormulaC6H5NO6S
Average Molecular Weight219.172
Monoisotopic Molecular Weight218.983757587
IUPAC Name(4-nitrophenyl)oxidanesulfonic acid
Traditional NameP-nitrophenyl sulfate
CAS Registry Number1080-04-2
SMILES
OS(=O)(=O)OC1=CC=C(C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C6H5NO6S/c8-7(9)5-1-3-6(4-2-5)13-14(10,11)12/h1-4H,(H,10,11,12)
InChI KeyJBGHTSSFSSUKLR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfuric acids and derivatives
Sub ClassArylsulfates
Direct ParentPhenylsulfates
Alternative Parents
Substituents
  • Phenylsulfate
  • Nitrobenzene
  • Phenoxy compound
  • Nitroaromatic compound
  • Monocyclic benzene moiety
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.85 g/LALOGPS
logP-0.66ALOGPS
logP1.13ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area109.42 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.36 m³·mol⁻¹ChemAxon
Polarizability17.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.16731661259
DarkChem[M-H]-145.52931661259
DeepCCS[M+H]+133.9630932474
DeepCCS[M-H]-130.73430932474
DeepCCS[M-2H]-166.23630932474
DeepCCS[M+Na]+142.0430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Nitrophenyl sulfateOS(=O)(=O)OC1=CC=C(C=C1)[N+]([O-])=O3298.3Standard polar33892256
4-Nitrophenyl sulfateOS(=O)(=O)OC1=CC=C(C=C1)[N+]([O-])=O1750.7Standard non polar33892256
4-Nitrophenyl sulfateOS(=O)(=O)OC1=CC=C(C=C1)[N+]([O-])=O1823.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Nitrophenyl sulfate,1TMS,isomer #1C[Si](C)(C)OS(=O)(=O)OC1=CC=C([N+](=O)[O-])C=C11882.4Semi standard non polar33892256
4-Nitrophenyl sulfate,1TMS,isomer #1C[Si](C)(C)OS(=O)(=O)OC1=CC=C([N+](=O)[O-])C=C11885.0Standard non polar33892256
4-Nitrophenyl sulfate,1TMS,isomer #1C[Si](C)(C)OS(=O)(=O)OC1=CC=C([N+](=O)[O-])C=C12865.3Standard polar33892256
4-Nitrophenyl sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C([N+](=O)[O-])C=C12180.2Semi standard non polar33892256
4-Nitrophenyl sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C([N+](=O)[O-])C=C12133.1Standard non polar33892256
4-Nitrophenyl sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C([N+](=O)[O-])C=C12890.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nitrophenyl sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-05tr-4920000000-45f7fddf73b73bdd28d32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nitrophenyl sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl sulfate 10V, Positive-QTOFsplash10-014i-0090000000-89388f0f0f30e89073372017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl sulfate 20V, Positive-QTOFsplash10-0fxx-1970000000-6983b98eb68128edbd282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl sulfate 40V, Positive-QTOFsplash10-03di-7900000000-7264bb6e0620339c6cd62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl sulfate 10V, Negative-QTOFsplash10-014i-0090000000-23f74544fd0af23171e52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl sulfate 20V, Negative-QTOFsplash10-014i-0090000000-abeed8e78d21382181dd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl sulfate 40V, Negative-QTOFsplash10-014i-3090000000-5345109ffb44bce853702017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl sulfate 10V, Positive-QTOFsplash10-014i-0090000000-b5b0700e293553b286e22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl sulfate 20V, Positive-QTOFsplash10-014i-0490000000-0a05ae2653fd63253a572021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl sulfate 40V, Positive-QTOFsplash10-0w90-9200000000-38c00ddd91d11825fd992021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl sulfate 10V, Negative-QTOFsplash10-014i-0090000000-b47717a646df2e797a012021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl sulfate 20V, Negative-QTOFsplash10-014i-0090000000-b47717a646df2e797a012021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl sulfate 40V, Negative-QTOFsplash10-014i-2090000000-a5fa3abcad50d19a5a252021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023939
KNApSAcK IDNot Available
Chemspider ID72581
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2320881
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound80349
PDB IDNot Available
ChEBI ID35422
Food Biomarker OntologyNot Available
VMH ID4NPHSF
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Almasi A, Fischer E, Perjesi P: A simple and rapid ion-pair HPLC method for simultaneous quantitation of 4-nitrophenol and its glucuronide and sulfate conjugates. J Biochem Biophys Methods. 2006 Nov 30;69(1-2):43-50. Epub 2006 May 7. [PubMed:16844228 ]
  2. Nielsen P, Friis C, Gyrd-Hansen N, Kraul I: Disposition of parathion in neonatal and young pigs. Pharmacol Toxicol. 1991 Oct;69(4):233-7. [PubMed:1956875 ]