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 and Quantified
Creation Date2006-03-10 10:50:46 UTC
Update Date2021-09-14 15:20:03 UTC
HMDB IDHMDB0001904
Secondary Accession Numbers
  • HMDB01904
Metabolite Identification
Common Name3-Nitrotyrosine
Description3-Nitrotyrosine, also known as nitrotyrosine is a product of tyrosine nitration mediated by reactive nitrogen species such as peroxynitrite anion and nitrogen dioxide. Nitrotyrosine is identified as an indicator or marker of cell damage, inflammation as well as NO (nitric oxide) production. Nitrotyrosine is formed in the presence of the active metabolite NO. Nitrotyrosine belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Structure
Data?1582752216
Synonyms
ValueSource
(2S)-2-Amino-3-(4-hydroxy-3-nitrophenyl)propanoic acidChEBI
L-3-NitrotyrosineChEBI
META-nitro-tyrosineChEBI
(2S)-2-Amino-3-(4-hydroxy-3-nitrophenyl)propanoateGenerator
3-MononitrotyrosineMeSH
3-Nitrotyrosine, (DL)-isomerMeSH
3-Nitrotyrosine, (L)-isomerMeSH
NitrotyrosineMeSH
Nitro-TyrosineMYCO, HMDB
5-NitrotyrosineHMDB
m-NitrotyrosineHMDB
3-NitrotyrosineChEBI
Chemical FormulaC9H10N2O5
Average Molecular Weight226.1861
Monoisotopic Molecular Weight226.05897144
IUPAC Name(2S)-2-amino-3-(4-hydroxy-3-nitrophenyl)propanoic acid
Traditional Namenitrotyrosine
CAS Registry Number3604-79-3
SMILES
N[C@@H](CC1=CC=C(O)C(=C1)[N+]([O-])=O)C(O)=O
InChI Identifier
InChI=1S/C9H10N2O5/c10-6(9(13)14)3-5-1-2-8(12)7(4-5)11(15)16/h1-2,4,6,12H,3,10H2,(H,13,14)/t6-/m0/s1
InChI KeyFBTSQILOGYXGMD-LURJTMIESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • Nitrophenol
  • L-alpha-amino acid
  • Nitrobenzene
  • Nitroaromatic compound
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • C-nitro compound
  • Amino acid
  • Organic nitro compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxoazanium
  • Organic zwitterion
  • Organonitrogen compound
  • Amine
  • Organic oxide
  • Organic nitrogen compound
  • Organooxygen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available158.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00002157
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.49 g/LALOGPS
logP10(-2.1) g/LALOGPS
logP10(-1.6) g/LChemAxon
logS10(-2.2) g/LALOGPS
pKa (Strongest Acidic)1.1ChemAxon
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area126.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.42 m³·mol⁻¹ChemAxon
Polarizability20.55 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]+153.11831661259
DarkChem[M-H]-149.30431661259
AllCCS[M+H]+149.01432859911
AllCCS[M-H]-146.01532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-NitrotyrosineN[C@@H](CC1=CC=C(O)C(=C1)[N+]([O-])=O)C(O)=O2890.1Standard polar33892256
3-NitrotyrosineN[C@@H](CC1=CC=C(O)C(=C1)[N+]([O-])=O)C(O)=O1924.5Standard non polar33892256
3-NitrotyrosineN[C@@H](CC1=CC=C(O)C(=C1)[N+]([O-])=O)C(O)=O2128.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Nitrotyrosine,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1[N+](=O)[O-]2196.9Semi standard non polar33892256
3-Nitrotyrosine,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C([N+](=O)[O-])=C12137.5Semi standard non polar33892256
3-Nitrotyrosine,1TMS,isomer #3C[Si](C)(C)N[C@@H](CC1=CC=C(O)C([N+](=O)[O-])=C1)C(=O)O2218.0Semi standard non polar33892256
3-Nitrotyrosine,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C)C([N+](=O)[O-])=C12202.3Semi standard non polar33892256
3-Nitrotyrosine,2TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C([N+](=O)[O-])=C1)C(=O)O2241.7Semi standard non polar33892256
3-Nitrotyrosine,2TMS,isomer #3C[Si](C)(C)N[C@@H](CC1=CC=C(O)C([N+](=O)[O-])=C1)C(=O)O[Si](C)(C)C2179.8Semi standard non polar33892256
3-Nitrotyrosine,2TMS,isomer #4C[Si](C)(C)N([C@@H](CC1=CC=C(O)C([N+](=O)[O-])=C1)C(=O)O)[Si](C)(C)C2337.8Semi standard non polar33892256
3-Nitrotyrosine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C([N+](=O)[O-])=C1)C(=O)O[Si](C)(C)C2238.2Semi standard non polar33892256
3-Nitrotyrosine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C([N+](=O)[O-])=C1)C(=O)O[Si](C)(C)C2238.7Standard non polar33892256
3-Nitrotyrosine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C)C([N+](=O)[O-])=C1)C(=O)O[Si](C)(C)C2493.0Standard polar33892256
3-Nitrotyrosine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1[N+](=O)[O-]2377.2Semi standard non polar33892256
3-Nitrotyrosine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1[N+](=O)[O-]2297.7Standard non polar33892256
3-Nitrotyrosine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1[N+](=O)[O-]2656.1Standard polar33892256
3-Nitrotyrosine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C([N+](=O)[O-])=C1)N([Si](C)(C)C)[Si](C)(C)C2330.3Semi standard non polar33892256
3-Nitrotyrosine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C([N+](=O)[O-])=C1)N([Si](C)(C)C)[Si](C)(C)C2326.8Standard non polar33892256
3-Nitrotyrosine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C([N+](=O)[O-])=C1)N([Si](C)(C)C)[Si](C)(C)C2656.7Standard polar33892256
3-Nitrotyrosine,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C([N+](=O)[O-])=C1)N([Si](C)(C)C)[Si](C)(C)C2420.6Semi standard non polar33892256
3-Nitrotyrosine,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C([N+](=O)[O-])=C1)N([Si](C)(C)C)[Si](C)(C)C2371.5Standard non polar33892256
3-Nitrotyrosine,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C)C([N+](=O)[O-])=C1)N([Si](C)(C)C)[Si](C)(C)C2386.9Standard polar33892256
3-Nitrotyrosine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)O)C=C1[N+](=O)[O-]2471.8Semi standard non polar33892256
3-Nitrotyrosine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O)C([N+](=O)[O-])=C12402.5Semi standard non polar33892256
3-Nitrotyrosine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C([N+](=O)[O-])=C1)C(=O)O2488.8Semi standard non polar33892256
3-Nitrotyrosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C12700.9Semi standard non polar33892256
3-Nitrotyrosine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C1)C(=O)O2764.1Semi standard non polar33892256
3-Nitrotyrosine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O)C([N+](=O)[O-])=C1)C(=O)O[Si](C)(C)C(C)(C)C2663.7Semi standard non polar33892256
3-Nitrotyrosine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=C(O)C([N+](=O)[O-])=C1)C(=O)O)[Si](C)(C)C(C)(C)C2832.1Semi standard non polar33892256
3-Nitrotyrosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C1)C(=O)O[Si](C)(C)C(C)(C)C2974.0Semi standard non polar33892256
3-Nitrotyrosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C1)C(=O)O[Si](C)(C)C(C)(C)C2889.7Standard non polar33892256
3-Nitrotyrosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C1)C(=O)O[Si](C)(C)C(C)(C)C2785.1Standard polar33892256
3-Nitrotyrosine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]3132.0Semi standard non polar33892256
3-Nitrotyrosine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2928.0Standard non polar33892256
3-Nitrotyrosine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2858.9Standard polar33892256
3-Nitrotyrosine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C([N+](=O)[O-])=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3044.9Semi standard non polar33892256
3-Nitrotyrosine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C([N+](=O)[O-])=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2975.7Standard non polar33892256
3-Nitrotyrosine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O)C([N+](=O)[O-])=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2846.3Standard polar33892256
3-Nitrotyrosine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3345.5Semi standard non polar33892256
3-Nitrotyrosine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3163.9Standard non polar33892256
3-Nitrotyrosine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2762.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Nitrotyrosine GC-MS (3 TMS)splash10-014i-2790000000-d2985346d8315d1d87942014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Nitrotyrosine GC-MS (Non-derivatized)splash10-014i-2790000000-d2985346d8315d1d87942017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Nitrotyrosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zgi-5910000000-077a7552abc426243e202017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Nitrotyrosine GC-MS (2 TMS) - 70eV, Positivesplash10-074l-9238000000-525285189da0213ff3c12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Nitrotyrosine 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 - 3-Nitrotyrosine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-0940000000-67e8e69b7a6cdee33f612012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-05o9-3900000000-fb63e13d7517f36968582012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0kdu-9600000000-31b19bfbe0c1fd17697f2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine , negative-QTOFsplash10-03di-0900000000-ee8213cb39c0e1019f312017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 20V, Positive-QTOFsplash10-00lr-3900000000-c2d41a5f34510f4276092021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 40V, Positive-QTOFsplash10-0rml-9500000000-caa9509a77fd0aa8355b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 10V, Positive-QTOFsplash10-001i-0920000000-a2b1b1fa9734a6b401892021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 35V, Positive-QTOFsplash10-001i-0900000000-a9d1a6fdb2c29984221e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 10V, Positive-QTOFsplash10-001i-0900000000-c18ef0ce904b7b49b8ec2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 20V, Positive-QTOFsplash10-00lr-1900000000-86a20e9368aceb49ba2e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 10V, Positive-QTOFsplash10-001i-0910000000-d885bb0a89378a0c95ee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 40V, Positive-QTOFsplash10-0mi6-9600000000-431eacf87ef25d0d67632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 35V, Negative-QTOFsplash10-03di-0900000000-57a8fbe1716064623e242021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 35V, Negative-QTOFsplash10-03ei-0900000000-a0d125a0ba852e048e8a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 20V, Positive-QTOFsplash10-00lr-1900000000-44b00fd33af2a259db2c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 40V, Positive-QTOFsplash10-00kf-9600000000-69dafe639edd5ba33f402021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 20V, Positive-QTOFsplash10-00lr-1900000000-fa3222f7814c77023fa12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 10V, Positive-QTOFsplash10-001i-0910000000-eb55137da6de91c54d492021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Nitrotyrosine 40V, Positive-QTOFsplash10-0gdl-9700000000-81bfe383cda5059c9bec2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Nitrotyrosine 10V, Positive-QTOFsplash10-004i-0090000000-cc8212643972d0c193362017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Nitrotyrosine 20V, Positive-QTOFsplash10-0gk9-0690000000-568913db0d42a193b3e32017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Nitrotyrosine 40V, Positive-QTOFsplash10-01vo-1920000000-4204e4cbcaf3737f8c1b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Nitrotyrosine 10V, Negative-QTOFsplash10-004i-0090000000-c60c74002b04ff989fbd2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Nitrotyrosine 20V, Negative-QTOFsplash10-004i-1090000000-088df2c70eeb38d1b7432017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Nitrotyrosine 40V, Negative-QTOFsplash10-00di-9120000000-8e492fc14553367e1dcb2017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Brain
  • Epidermis
  • Fibroblasts
  • Neuron
  • Platelet
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0-0.30 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.85 +/- 1.98 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified3.36 (2.81-3.91) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00148-0.0253 uMNot SpecifiedNot Specified
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.25 +/- 0.11 uMNewborn (0-30 days old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.81+/- 0.45 uMAdult (>18 years old)BothOxidative and nitrosative stress details
Cerebrospinal Fluid (CSF)Detected and Quantified5.54 (3.99-7.09) uMAdult (>18 years old)Both
Meningitis
details
Cerebrospinal Fluid (CSF)Detected and Quantified22.4-97.6 uMAdult (>18 years old)Not SpecifiedTraumatic brain injury (TBI) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.45 +/- 0.33 uMNewborn (0-30 days old)Not SpecifiedHypoxic-ischemic encephalopathy details
Associated Disorders and Diseases
Disease References
Oxidative stress
  1. Rossner P Jr, Svecova V, Milcova A, Lnenickova Z, Solansky I, Santella RM, Sram RJ: Oxidative and nitrosative stress markers in bus drivers. Mutat Res. 2007 Apr 1;617(1-2):23-32. Epub 2007 Feb 4. [PubMed:17328930 ]
Meningitis
  1. Kastenbauer S, Koedel U, Becker BF, Pfister HW: Oxidative stress in bacterial meningitis in humans. Neurology. 2002 Jan 22;58(2):186-91. [PubMed:11805243 ]
Head injury
  1. Darwish RS, Amiridze N, Aarabi B: Nitrotyrosine as an oxidative stress marker: evidence for involvement in neurologic outcome in human traumatic brain injury. J Trauma. 2007 Aug;63(2):439-42. [PubMed:17693848 ]
Hypoxic-ischemic encephalopathy
  1. Gucuyener K, Ergenekon E, Demiryurek T, Erbas D, Ozturk G, Koc E, Atalay Y: Cerebrospinal fluid levels of nitric oxide and nitrotyrosine in neonates with mild hypoxic-ischemic encephalopathy. J Child Neurol. 2002 Nov;17(11):815-8. [PubMed:12585720 ]
Associated OMIM IDsNone
DrugBank IDDB03867
Phenol Explorer Compound IDNot Available
FooDB IDFDB022731
KNApSAcK IDNot Available
Chemspider ID58633
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNitrotyrosine
METLIN ID6383
PubChem Compound65124
PDB IDNot Available
ChEBI ID44454
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000356
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kastenbauer S, Koedel U, Becker BF, Pfister HW: Oxidative stress in bacterial meningitis in humans. Neurology. 2002 Jan 22;58(2):186-91. [PubMed:11805243 ]
  2. Gaut JP, Byun J, Tran HD, Heinecke JW: Artifact-free quantification of free 3-chlorotyrosine, 3-bromotyrosine, and 3-nitrotyrosine in human plasma by electron capture-negative chemical ionization gas chromatography mass spectrometry and liquid chromatography-electrospray ionization tandem mass spectrometry. Anal Biochem. 2002 Jan 15;300(2):252-9. [PubMed:11779118 ]
  3. Blanchard-Fillion B, Prou D, Polydoro M, Spielberg D, Tsika E, Wang Z, Hazen SL, Koval M, Przedborski S, Ischiropoulos H: Metabolism of 3-nitrotyrosine induces apoptotic death in dopaminergic cells. J Neurosci. 2006 Jun 7;26(23):6124-30. [PubMed:16763020 ]
  4. Isobe C, Abe T, Kikuchi T, Murata T, Sato C, Terayama Y: Cabergoline scavenges peroxynitrite enhanced by L-DOPA therapy in patients with Parkinson's disease. Eur J Neurol. 2006 Apr;13(4):346-50. [PubMed:16643311 ]
  5. Ferrante RJ, Shinobu LA, Schulz JB, Matthews RT, Thomas CE, Kowall NW, Gurney ME, Beal MF: Increased 3-nitrotyrosine and oxidative damage in mice with a human copper/zinc superoxide dismutase mutation. Ann Neurol. 1997 Sep;42(3):326-34. [PubMed:9307254 ]
  6. Sanyal AJ, Campbell-Sargent C, Mirshahi F, Rizzo WB, Contos MJ, Sterling RK, Luketic VA, Shiffman ML, Clore JN: Nonalcoholic steatohepatitis: association of insulin resistance and mitochondrial abnormalities. Gastroenterology. 2001 Apr;120(5):1183-92. [PubMed:11266382 ]
  7. Oates JC, Christensen EF, Reilly CM, Self SE, Gilkeson GS: Prospective measure of serum 3-nitrotyrosine levels in systemic lupus erythematosus: correlation with disease activity. Proc Assoc Am Physicians. 1999 Nov-Dec;111(6):611-21. [PubMed:10591091 ]
  8. Schwedhelm E, Tsikas D, Gutzki FM, Frolich JC: Gas chromatographic-tandem mass spectrometric quantification of free 3-nitrotyrosine in human plasma at the basal state. Anal Biochem. 1999 Dec 15;276(2):195-203. [PubMed:10603243 ]
  9. Tohgi H, Abe T, Yamazaki K, Murata T, Ishizaki E, Isobe C: Remarkable increase in cerebrospinal fluid 3-nitrotyrosine in patients with sporadic amyotrophic lateral sclerosis. Ann Neurol. 1999 Jul;46(1):129-31. [PubMed:10401792 ]
  10. Kaur H, Halliwell B: Evidence for nitric oxide-mediated oxidative damage in chronic inflammation. Nitrotyrosine in serum and synovial fluid from rheumatoid patients. FEBS Lett. 1994 Aug 15;350(1):9-12. [PubMed:8062931 ]
  11. Kaur H, Lyras L, Jenner P, Halliwell B: Artefacts in HPLC detection of 3-nitrotyrosine in human brain tissue. J Neurochem. 1998 May;70(5):2220-3. [PubMed:9572312 ]
  12. Abu-Qare AW, Abou-Donia MB: Combined exposure to DEET (N,N-diethyl-m-toluamide) and permethrin: pharmacokinetics and toxicological effects. J Toxicol Environ Health B Crit Rev. 2003 Jan-Feb;6(1):41-53. [PubMed:12587253 ]
  13. Takasaki A, Nezirevic D, Arstrand K, Wakamatsu K, Ito S, Kagedal B: HPLC analysis of pheomelanin degradation products in human urine. Pigment Cell Res. 2003 Oct;16(5):480-6. [PubMed:12950724 ]
  14. Delatour T: Performance of quantitative analyses by liquid chromatography-electrospray ionisation tandem mass spectrometry: from external calibration to isotopomer-based exact matching. Anal Bioanal Chem. 2004 Oct;380(3):515-23. Epub 2004 Aug 31. [PubMed:15340769 ]
  15. Yi D, Ingelse BA, Duncan MW, Smythe GA: Quantification of 3-nitrotyrosine in biological tissues and fluids: generating valid results by eliminating artifactual formation. J Am Soc Mass Spectrom. 2000 Jun;11(6):578-86. [PubMed:10833032 ]
  16. Shuker DE, Prevost V, Friesen MD, Lin D, Ohshima H, Bartsch H: Urinary markers for measuring exposure to endogenous and exogenous alkylating agents and precursors. Environ Health Perspect. 1993 Mar;99:33-7. [PubMed:8319651 ]