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Record Information
Version3.6
Creation Date2006-03-10 10:50:46 UTC
Update Date2016-02-11 01:05:05 UTC
HMDB IDHMDB01904
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Nitrotyrosine
Description3-Nitrotyrosine (NTyr) is formed in vivo in tissue or blood proteins after exposure to nitrosating and/or nitrating agents such as tetranitromethane. (PMID 8319651 ). Reactive nitrogen species such as peroxynitrite can nitrate specific amino acids, whether free or protein bound, and 3-nitrotyrosine is believed to be one marker of this reaction. (PMID 10833032 ).
Structure
Thumb
Synonyms
ValueSource
(2S)-2-amino-3-(4-Hydroxy-3-nitrophenyl)propanoic acidChEBI
3-NitrotyrosineChEBI
L-3-NitrotyrosineChEBI
(2S)-2-amino-3-(4-Hydroxy-3-nitrophenyl)propanoateGenerator
5-NitrotyrosineHMDB
m-NitrotyrosineHMDB
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 KeyInChIKey=FBTSQILOGYXGMD-LURJTMIESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • L-alpha-amino acid
  • Nitrophenol derivative
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Nitrobenzene
  • Aralkylamine
  • Phenol
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic nitro compound
  • Organic nitrite
  • C-nitro compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic salt
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Organic zwitterion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.49 mg/mLALOGPS
logP-2.1ALOGPS
logP-1.6ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.96ChemAxon
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area129.37 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.42 m3·mol-1ChemAxon
Polarizability20.52 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-2790000000-d2985346d8315d1d8794View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0940000000-67e8e69b7a6cdee33f61View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05o9-3900000000-fb63e13d7517f3696858View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0kdu-9600000000-31b19bfbe0c1fd17697fView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Brain
  • Brain Plaques
  • Epidermis
  • Fibroblasts
  • Muscle
  • Neuron
  • Platelet
  • Spinal Cord
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 ApplicableNot AvailableNot AvailableNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
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. [11805243 ]
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. [17328930 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022731
KNApSAcK IDNot Available
Chemspider ID58633
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01904
Metagene LinkHMDB01904
METLIN ID6383
PubChem Compound65124
PDB IDNIY
ChEBI ID44454
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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [8319651 ]