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Record Information
StatusDetected and Quantified
Creation Date2006-03-10 10:50:46 UTC
Update Date2020-04-23 20:55:51 UTC
Secondary Accession Numbers
  • HMDB01904
Metabolite Identification
Common Name3-Nitrotyrosine
Description3-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. 3-Nitrotyrosine is a very strong basic compound (based on its pKa).
(2S)-2-Amino-3-(4-hydroxy-3-nitrophenyl)propanoic acidChEBI
3-Nitrotyrosine, (L)-isomerHMDB
3-Nitrotyrosine, (DL)-isomerHMDB
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
InChI Identifier
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
  • 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
Physiological effect

Health effect:



Biological location:


Naturally occurring process:


Industrial application:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility1.49 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
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-2790000000-d2985346d8315d1d8794Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-2790000000-d2985346d8315d1d8794Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zgi-5910000000-077a7552abc426243e20Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-074l-9238000000-525285189da0213ff3c1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0940000000-67e8e69b7a6cdee33f61Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05o9-3900000000-fb63e13d7517f3696858Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0kdu-9600000000-31b19bfbe0c1fd17697fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-03di-0900000000-ee8213cb39c0e1019f31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-cc8212643972d0c19336Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gk9-0690000000-568913db0d42a193b3e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01vo-1920000000-4204e4cbcaf3737f8c1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-c60c74002b04ff989fbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1090000000-088df2c70eeb38d1b743Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9120000000-8e492fc14553367e1dcbSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Brain
  • Epidermis
  • Fibroblasts
  • Neuron
  • Platelet
  • Skeletal Muscle
Normal Concentrations
BloodDetected and Quantified0.0-0.30 uMAdult (>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
Cerebrospinal Fluid (CSF)Detected and Quantified0.25 +/- 0.11 uMNewborn (0-30 days old)Not SpecifiedNormal details
UrineDetected but not Quantified Not AvailableNot AvailableNormal details
Abnormal Concentrations
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
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 ]
  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
PubChem Compound65124
PDB IDNot Available
ChEBI ID44454
Food Biomarker OntologyNot Available
VMH IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  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. 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 ]
  16. 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 ]