Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2017-03-21 06:14:48 UTC
Update Date2019-07-23 07:18:27 UTC
HMDB IDHMDB0062403
Secondary Accession Numbers
  • HMDB62403
Metabolite Identification
Common Name4-hydroxy-3-nitrophenylacetate
Description4-hydroxy-3-nitrophenylacetate, also known as 3-nitro-4-hydroxyphenylacetic acid, is slightly soluble (in water). It is a mildly acidic compound. This metabolite is a member of the class of 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. Free nitrotyrosine undergoes metabolism to form 3-nitro-4-hydroxyphenylacetic acid (NHPA) which is excreted in the urine (Wikipedia). However, it is not known whether NHPA is derived exclusively from metabolism of nitrotyrosine, or whether it can be formed by nitration of circulating para -hydroxyphenylacetic acid (PHPA), a metabolite of tyrosine (PMID: 12797864 ). Since the plasma concentration of PHPA is markedly higher than free nitrotyrosine (approx. 400-fold), the nitration of high-circulating endogenous PHPA to form NHPA becomes very significant and accounts for the majority of NHPA excreted in urine (PMID: 12797864 ).
Structure
Data?1563866307
Synonyms
ValueSource
2-(4-HYDROXY-3-nitrophenyl)acetIC ACIDChEBI
4-Hydroxy-3-nitrophenylacetic acidChEBI
NO2hpaChEBI
2-(4-HYDROXY-3-nitrophenyl)acetateGenerator
NP-HaptenHMDB
Hapten NPHMDB
(4-Hydroxy-3-nitrophenyl)acetylHMDB
4-Hydroxy-3-nitrophenylacetylHMDB
3-Nitro-4-hydroxyphenylacetic acidHMDB
4-OHNOPHAXHMDB
4-Hydroxy-3-nitrophenyl acetylHMDB
4-Hydroxy-5-nitrophenyl acetic acidHMDB
4-Hydroxy-3-nitrophenylacetateGenerator
Chemical FormulaC8H7NO5
Average Molecular Weight197.1449
Monoisotopic Molecular Weight197.032422339
IUPAC Name2-(4-hydroxy-3-nitrophenyl)acetic acid
Traditional Name(4-hydroxy-3-nitrophenyl)acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC1=CC(=C(O)C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C8H7NO5/c10-7-2-1-5(4-8(11)12)3-6(7)9(13)14/h1-3,10H,4H2,(H,11,12)
InChI KeyQBHBHOSRLDPIHG-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
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • C-nitro compound
  • Organic nitro compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.74 g/lALOGPS
LogP1.14ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.01ALOGPS
logP1.25ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.02ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.67 m³·mol⁻¹ChemAxon
Polarizability17.1 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]+144.15431661259
DarkChem[M-H]-141.39131661259
DeepCCS[M+H]+134.63130932474
DeepCCS[M-H]-131.37130932474
DeepCCS[M-2H]-167.25130932474
DeepCCS[M+Na]+142.9630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-hydroxy-3-nitrophenylacetateOC(=O)CC1=CC(=C(O)C=C1)[N+]([O-])=O2870.8Standard polar33892256
4-hydroxy-3-nitrophenylacetateOC(=O)CC1=CC(=C(O)C=C1)[N+]([O-])=O1558.1Standard non polar33892256
4-hydroxy-3-nitrophenylacetateOC(=O)CC1=CC(=C(O)C=C1)[N+]([O-])=O1762.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-hydroxy-3-nitrophenylacetate,1TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CC=C(O)C([N+](=O)[O-])=C11857.8Semi standard non polar33892256
4-hydroxy-3-nitrophenylacetate,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(CC(=O)O)C=C1[N+](=O)[O-]1892.3Semi standard non polar33892256
4-hydroxy-3-nitrophenylacetate,2TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CC=C(O[Si](C)(C)C)C([N+](=O)[O-])=C11968.3Semi standard non polar33892256
4-hydroxy-3-nitrophenylacetate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=C(O)C([N+](=O)[O-])=C12108.8Semi standard non polar33892256
4-hydroxy-3-nitrophenylacetate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CC(=O)O)C=C1[N+](=O)[O-]2194.1Semi standard non polar33892256
4-hydroxy-3-nitrophenylacetate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C12455.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxy-3-nitrophenylacetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-6900000000-e5a377fa30be1cf9599c2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxy-3-nitrophenylacetate 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-hydroxy-3-nitrophenylacetate 10V, Positive-QTOFsplash10-0002-0900000000-79a4c32d8d4140950f152017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 20V, Positive-QTOFsplash10-006x-0900000000-f46310eb481a53ce8a732017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 40V, Positive-QTOFsplash10-006y-2900000000-1198cd045e8ca04126ed2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 10V, Negative-QTOFsplash10-0002-0900000000-edf1df88d14334cd76092017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 20V, Negative-QTOFsplash10-0002-1900000000-de624db331c7d7c2ad292017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 40V, Negative-QTOFsplash10-0a4i-9400000000-fd42775792f6028d92ba2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 10V, Negative-QTOFsplash10-001i-0900000000-4322905b69ee20c9fe7b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 20V, Negative-QTOFsplash10-0zgi-0900000000-32060e9dd1d20b4cbfba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 40V, Negative-QTOFsplash10-0002-9600000000-ddfb1263633ffe02e6082021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 10V, Positive-QTOFsplash10-0002-0900000000-cd198104c5c4f1e9625d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 20V, Positive-QTOFsplash10-0udj-0900000000-740cc01eff010d7e68262021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 40V, Positive-QTOFsplash10-0a4i-8900000000-e126a2d3aff76df1c47b2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08294
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound447364
PDB IDNPA
ChEBI ID546274
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. Takahama U, Oniki T, Murata H: The presence of 4-hydroxyphenylacetic acid in human saliva and the possibility of its nitration by salivary nitrite in the stomach. FEBS Lett. 2002 May 8;518(1-3):116-8. [PubMed:11997029 ]
  2. Mani AR, Pannala AS, Orie NN, Ollosson R, Harry D, Rice-Evans CA, Moore KP: Nitration of endogenous para-hydroxyphenylacetic acid and the metabolism of nitrotyrosine. Biochem J. 2003 Sep 1;374(Pt 2):521-7. [PubMed:12797864 ]