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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:19 UTC
Update Date2023-02-21 17:16:29 UTC
HMDB IDHMDB0002916
Secondary Accession Numbers
  • HMDB0062694
  • HMDB02916
  • HMDB62694
Metabolite Identification
Common Name4-Nitrocatechol
Description4-Nitrocatechol 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-Nitrocatechol exists in all living organisms, ranging from bacteria to humans. 4-Nitrocatechol has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 4-nitrocatechol a potential biomarker for the consumption of these foods. 4-Nitrocatechol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 4-Nitrocatechol.
Structure
Data?1676999789
Synonyms
ValueSource
1,2-Dihydroxy-4-nitrobenzeneChEBI
4-NitropyrocatecholChEBI
3,4-Dihydroxy-1-nitrobenzeneHMDB
3,4-DihydroxynitrobenzeneHMDB
4-nitro-1,2-BenzenediolHMDB
4-nitro-1,2-DihydroxybenzeneHMDB
4-nitro-Pyrocatechol4-nitropyrocatechol NSC 80651HMDB
4-NitrobenzcatechinHMDB
P-NitrocatecholHMDB
2-Hydroxy-4-nitrophenolateHMDB
4-Nitro-1,2-benzenediolHMDB
4-Nitro-1,2-dihydroxybenzeneHMDB
4-NitrocatecholHMDB
p-NitrocatecholHMDB
Chemical FormulaC6H5NO4
Average Molecular Weight155.1082
Monoisotopic Molecular Weight155.021857653
IUPAC Name4-nitrobenzene-1,2-diol
Traditional Name4-nitrocatechol
CAS Registry Number3316-09-4
SMILES
OC1=C(O)C=C(C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C6H5NO4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H
InChI KeyXJNPNXSISMKQEX-UHFFFAOYSA-N
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
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point174 - 176 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.66HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.76 g/LALOGPS
logP1.26ALOGPS
logP1.31ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)7.18ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.34 m³·mol⁻¹ChemAxon
Polarizability13.12 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]+132.78131661259
DarkChem[M-H]-129.8431661259
DeepCCS[M+H]+131.95330932474
DeepCCS[M-H]-128.6530932474
DeepCCS[M-2H]-165.630932474
DeepCCS[M+Na]+140.60330932474
AllCCS[M+H]+132.332859911
AllCCS[M+H-H2O]+127.832859911
AllCCS[M+NH4]+136.532859911
AllCCS[M+Na]+137.732859911
AllCCS[M-H]-125.232859911
AllCCS[M+Na-2H]-126.432859911
AllCCS[M+HCOO]-127.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-NitrocatecholOC1=C(O)C=C(C=C1)[N+]([O-])=O3237.3Standard polar33892256
4-NitrocatecholOC1=C(O)C=C(C=C1)[N+]([O-])=O1529.4Standard non polar33892256
4-NitrocatecholOC1=C(O)C=C(C=C1)[N+]([O-])=O1742.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Nitrocatechol,1TMS,isomer #1C[Si](C)(C)OC1=CC=C([N+](=O)[O-])C=C1O1654.4Semi standard non polar33892256
4-Nitrocatechol,1TMS,isomer #2C[Si](C)(C)OC1=CC([N+](=O)[O-])=CC=C1O1594.0Semi standard non polar33892256
4-Nitrocatechol,2TMS,isomer #1C[Si](C)(C)OC1=CC=C([N+](=O)[O-])C=C1O[Si](C)(C)C1687.5Semi standard non polar33892256
4-Nitrocatechol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([N+](=O)[O-])C=C1O1940.2Semi standard non polar33892256
4-Nitrocatechol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC([N+](=O)[O-])=CC=C1O1854.3Semi standard non polar33892256
4-Nitrocatechol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([N+](=O)[O-])C=C1O[Si](C)(C)C(C)(C)C2197.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Nitrocatechol GC-EI-TOF (Non-derivatized)splash10-001s-1950000000-faaf15fd1ec113f2b54e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrocatechol GC-EI-TOF (Non-derivatized)splash10-001s-1950000000-faaf15fd1ec113f2b54e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrocatechol GC-EI-TOF (Non-derivatized)splash10-001s-1950000000-faaf15fd1ec113f2b54e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrocatechol GC-EI-TOF (Non-derivatized)splash10-001s-1950000000-faaf15fd1ec113f2b54e2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nitrocatechol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-02b39e2d157c3829375f2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nitrocatechol GC-MS (2 TMS) - 70eV, Positivesplash10-00di-8390000000-9ce3af1465a211c62c082017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nitrocatechol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nitrocatechol 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-Nitrocatechol 35V, Negative-QTOFsplash10-0fk9-1900000000-20992826e1c86b0422452021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrocatechol 10V, Positive-QTOFsplash10-0a4i-0900000000-cf479fcf220611c7c2822017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrocatechol 20V, Positive-QTOFsplash10-0002-0900000000-a438cfc44009c80ae2b12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrocatechol 40V, Positive-QTOFsplash10-0f92-3900000000-6a688f91418ed25d4aad2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrocatechol 10V, Negative-QTOFsplash10-0udi-0900000000-3a1438af5cfdd1a764532017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrocatechol 20V, Negative-QTOFsplash10-0udi-0900000000-64163bd65bd38adfb2cf2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrocatechol 40V, Negative-QTOFsplash10-0udl-3900000000-f9fb9e7b1ada6519c0872017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrocatechol 10V, Positive-QTOFsplash10-0a4i-0900000000-dd65e28b5507a1abfb0e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrocatechol 20V, Positive-QTOFsplash10-0a4i-2900000000-ff3f84d5fc5d45d608e52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrocatechol 40V, Positive-QTOFsplash10-0udi-9000000000-db86a62064c6c13c16392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrocatechol 10V, Negative-QTOFsplash10-0udi-0900000000-c23d0f4048cedb728ea22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrocatechol 20V, Negative-QTOFsplash10-0udi-2900000000-0a7ee2badf00f8f5f00e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrocatechol 40V, Negative-QTOFsplash10-0002-9000000000-a0441e6336543cb884232021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX 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 IDDB03407
Phenol Explorer Compound IDNot Available
FooDB IDFDB023081
KNApSAcK IDNot Available
Chemspider ID2745027
KEGG Compound IDC02235
BioCyc IDCPD-158
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3505109
PDB IDNot Available
ChEBI ID16318
Food Biomarker OntologyNot Available
VMH ID24NPH
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tassaneeyakul W, Veronese ME, Birkett DJ, Gonzalez FJ, Miners JO: Validation of 4-nitrophenol as an in vitro substrate probe for human liver CYP2E1 using cDNA expression and microsomal kinetic techniques. Biochem Pharmacol. 1993 Dec 3;46(11):1975-81. [PubMed:8267647 ]
  2. Duescher RJ, Elfarra AA: Determination of p-nitrophenol hydroxylase activity of rat liver microsomes by high-pressure liquid chromatography. Anal Biochem. 1993 Aug 1;212(2):311-4. [PubMed:8214571 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
Reactions
4-Nitrophenol + NADPH + Oxygen → 4-Nitrocatechol + NADP + Waterdetails