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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 21:15:04 UTC
Update Date2022-03-07 03:17:42 UTC
HMDB IDHMDB0060272
Secondary Accession Numbers
  • HMDB60272
Metabolite Identification
Common Name4-Nitrophenyl phosphate
Description4-Nitrophenyl phosphate, also known as nitrophenylphosphoric acid, belongs to the class of organic compounds known as phenyl phosphates. These are aromatic organooxygen compounds containing a phosphate group, which is O-esterified with a phenyl group. These are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both an hydroxyl group and a nitro group on two different ring carbon atoms.
Structure
Data?1563866037
Synonyms
ValueSource
NitrophenylphosphateChEBI
p-Nitrophenyl dihydrogen phosphateChEBI
p-Nitrophenyl phosphateChEBI
Phosphoric acid, mono(4-nitrophenyl) esterChEBI
Phosphoric acid, mono(p-nitrophenyl) esterChEBI
Nitrophenylphosphoric acidGenerator
p-Nitrophenyl dihydrogen phosphoric acidGenerator
p-Nitrophenyl phosphoric acidGenerator
Phosphate, mono(4-nitrophenyl) esterGenerator
Phosphate, mono(p-nitrophenyl) esterGenerator
4-Nitrophenyl phosphoric acidGenerator
Disodium nitrophenylphosphateHMDB
Diammonium nitrophenylphosphateHMDB
Sodium nitrophenylphosphateHMDB
Dipotassium nitrophenylphosphateHMDB
Magnesium nitrophenylphosphateHMDB
Monosodium nitrophenylphosphateHMDB
4-NitrophenylphosphateHMDB
p-Nitrophenol phosphateHMDB
Chemical FormulaC6H6NO6P
Average Molecular Weight219.0887
Monoisotopic Molecular Weight218.993273441
IUPAC Name(4-nitrophenoxy)phosphonic acid
Traditional Name4-nitrophenyl phosphate
CAS Registry NumberNot Available
SMILES
OP(O)(=O)OC1=CC=C(C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C6H6NO6P/c8-7(9)5-1-3-6(4-2-5)13-14(10,11)12/h1-4H,(H2,10,11,12)
InChI KeyXZKIHKMTEMTJQX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenyl phosphates. These are aromatic organooxygen compounds containing a phosphate group, which is O-esterified with a phenyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentPhenyl phosphates
Alternative Parents
Substituents
  • Phenyl phosphate
  • Nitrobenzene
  • Phenoxy compound
  • Nitroaromatic compound
  • Monocyclic benzene moiety
  • Benzenoid
  • 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
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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 Solubility1.03 g/LALOGPS
logP0.5ALOGPS
logP0.96ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area109.9 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.23 m³·mol⁻¹ChemAxon
Polarizability16.61 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.61331661259
DarkChem[M-H]-146.0631661259
DeepCCS[M+H]+120.99730932474
DeepCCS[M-H]-117.8930932474
DeepCCS[M-2H]-154.03230932474
DeepCCS[M+Na]+129.04230932474
AllCCS[M+H]+145.432859911
AllCCS[M+H-H2O]+141.432859911
AllCCS[M+NH4]+149.032859911
AllCCS[M+Na]+150.132859911
AllCCS[M-H]-137.932859911
AllCCS[M+Na-2H]-138.432859911
AllCCS[M+HCOO]-139.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Nitrophenyl phosphateOP(O)(=O)OC1=CC=C(C=C1)[N+]([O-])=O3084.3Standard polar33892256
4-Nitrophenyl phosphateOP(O)(=O)OC1=CC=C(C=C1)[N+]([O-])=O1869.6Standard non polar33892256
4-Nitrophenyl phosphateOP(O)(=O)OC1=CC=C(C=C1)[N+]([O-])=O1932.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Nitrophenyl phosphate,1TMS,isomer #1C[Si](C)(C)OP(=O)(O)OC1=CC=C([N+](=O)[O-])C=C11968.6Semi standard non polar33892256
4-Nitrophenyl phosphate,1TMS,isomer #1C[Si](C)(C)OP(=O)(O)OC1=CC=C([N+](=O)[O-])C=C11902.4Standard non polar33892256
4-Nitrophenyl phosphate,1TMS,isomer #1C[Si](C)(C)OP(=O)(O)OC1=CC=C([N+](=O)[O-])C=C12567.7Standard polar33892256
4-Nitrophenyl phosphate,2TMS,isomer #1C[Si](C)(C)OP(=O)(OC1=CC=C([N+](=O)[O-])C=C1)O[Si](C)(C)C1984.3Semi standard non polar33892256
4-Nitrophenyl phosphate,2TMS,isomer #1C[Si](C)(C)OP(=O)(OC1=CC=C([N+](=O)[O-])C=C1)O[Si](C)(C)C2029.3Standard non polar33892256
4-Nitrophenyl phosphate,2TMS,isomer #1C[Si](C)(C)OP(=O)(OC1=CC=C([N+](=O)[O-])C=C1)O[Si](C)(C)C2242.9Standard polar33892256
4-Nitrophenyl phosphate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=C([N+](=O)[O-])C=C12270.5Semi standard non polar33892256
4-Nitrophenyl phosphate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=C([N+](=O)[O-])C=C12118.5Standard non polar33892256
4-Nitrophenyl phosphate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(O)OC1=CC=C([N+](=O)[O-])C=C12679.4Standard polar33892256
4-Nitrophenyl phosphate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C([N+](=O)[O-])C=C1)O[Si](C)(C)C(C)(C)C2498.0Semi standard non polar33892256
4-Nitrophenyl phosphate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C([N+](=O)[O-])C=C1)O[Si](C)(C)C(C)(C)C2449.4Standard non polar33892256
4-Nitrophenyl phosphate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C([N+](=O)[O-])C=C1)O[Si](C)(C)C(C)(C)C2460.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenyl phosphate GC-EI-TOF (Non-derivatized)splash10-01pt-1953000000-f98c304b3a6ab9cd2c5d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenyl phosphate GC-EI-TOF (Non-derivatized)splash10-01pt-1953000000-f98c304b3a6ab9cd2c5d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nitrophenyl phosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0hn0-3920000000-657f264f7fae018264572016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nitrophenyl phosphate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenyl phosphate LC-ESI-QQ , negative-QTOFsplash10-014i-3090000000-f21aa9ac1a47ee6f31252017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenyl phosphate LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-c63df6191601e73b27fb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenyl phosphate LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-1dd228dda161ae54601f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenyl phosphate LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-7aa2269324d3d40f4c382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenyl phosphate LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-90c742e07486b602e9c02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenyl phosphate LC-ESI-QTOF , negative-QTOFsplash10-004i-9000000000-d99bb72e9136380d86982017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenyl phosphate LC-ESI-QTOF , negative-QTOFsplash10-004i-9000000000-027da95acd3eda7ca2432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenyl phosphate LC-ESI-QTOF , negative-QTOFsplash10-004i-9000000000-261d7b5a3ed6f38c7b782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenyl phosphate LC-ESI-QTOF , positive-QTOFsplash10-00dl-9550000000-2caf54e289b4f89bf43f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenyl phosphate 30V, Negative-QTOFsplash10-004i-9000000000-027da95acd3eda7ca2432021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl phosphate 10V, Positive-QTOFsplash10-00di-2090000000-bf49b02fd8accd28c0ea2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl phosphate 20V, Positive-QTOFsplash10-03dl-1690000000-65b1343789f97a63c59f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl phosphate 40V, Positive-QTOFsplash10-001j-8910000000-0c83bc1df690856d218a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl phosphate 10V, Negative-QTOFsplash10-0159-5090000000-4730832a25320a38eaf92015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl phosphate 20V, Negative-QTOFsplash10-02u0-9170000000-08a8302b031ef8d357632015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenyl phosphate 40V, Negative-QTOFsplash10-002b-9000000000-d53bff0ab80eab337c472015-09-15Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDDB04214
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC03360
BioCyc IDCPD-194
BiGG IDNot Available
Wikipedia LinkPara-Nitrophenylphosphate
METLIN IDNot Available
PubChem Compound378
PDB ID4NP
ChEBI ID17440
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Enzymes

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 + Phosphatedetails
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 + Phosphatedetails
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 + Phosphatedetails
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 + Phosphatedetails