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
Version3.6
Creation Date2006-02-28 10:36:16 UTC
Update Date2016-02-11 01:05:04 UTC
HMDB IDHMDB01885
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Chlorotyrosine
Description3-Chlorotyrosine, a specific marker of myeloperoxidase-catalyzed oxidation, is markedly elevated in low density lipoprotein isolated from human atherosclerotic intima. (PMID 9151778 ). In particular, myeloperoxidase halogenates tyrosine residues in plasma proteins and and generates 3-chlorotyrosine (CY). The detection of free chlorotyrosine in blood or urine arises from the degradation of these chlorinated proteins. CY concentrations may be useful for monitoring the activation of neutrophils in asthmatic patients (PMID 15196282 ).
Structure
Thumb
Synonyms
ValueSource
3-chloro-L-TyrosineHMDB
ChlorotyrosineHMDB
L-(8CI)-3-chloro-tyrosineHMDB
MonochlorotyrosineHMDB
Chemical FormulaC9H10ClNO3
Average Molecular Weight215.634
Monoisotopic Molecular Weight215.034920898
IUPAC Name2-amino-3-(3-chloro-4-hydroxyphenyl)propanoic acid
Traditional Namemonochlorotyrosine
CAS Registry Number7423-93-0
SMILES
NC(CC1=CC(Cl)=C(O)C=C1)C(O)=O
InChI Identifier
InChI=1S/C9H10ClNO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)
InChI KeyInChIKey=ACWBBAGYTKWBCD-UHFFFAOYSA-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
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • 2-chlorophenol
  • 2-halophenol
  • Aralkylamine
  • Phenol
  • Halobenzene
  • Chlorobenzene
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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 Solubility1.01 mg/mLALOGPS
logP-1.6ALOGPS
logP-0.89ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
pKa (Strongest Basic)9.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.9 m3·mol-1ChemAxon
Polarizability20.35 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01b9-0970000000-69b92cf990ab75e60cd9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-0900000000-efa66d19cc56269a53f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-003i-0900000000-d47f0bce2c489e27a354View 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
  • Urine
Tissue Location
  • Neutrophil
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified6.96 +/- 3.578 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.0007 +/- 0.0005 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.58 +/- 0.18 uMAdult (>18 years old)BothMyocardial infarction details
UrineDetected and Quantified10.886 +/- 8.573 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.0023 +/- 0.0016 umol/mmol creatinineAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease References
Asthma
  1. Mita H, Higashi N, Taniguchi M, Higashi A, Kawagishi Y, Akiyama K: Urinary 3-bromotyrosine and 3-chlorotyrosine concentrations in asthmatic patients: lack of increase in 3-bromotyrosine concentration in urine and plasma proteins in aspirin-induced asthma after intravenous aspirin challenge. Clin Exp Allergy. 2004 Jun;34(6):931-8. [15196282 ]
Myocardial infarction
  1. Mocatta TJ, Pilbrow AP, Cameron VA, Senthilmohan R, Frampton CM, Richards AM, Winterbourn CC: Plasma concentrations of myeloperoxidase predict mortality after myocardial infarction. J Am Coll Cardiol. 2007 May 22;49(20):1993-2000. Epub 2007 May 4. [17512353 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022723
KNApSAcK IDNot Available
Chemspider ID106510
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01885
Metagene LinkHMDB01885
METLIN ID6369
PubChem Compound119226
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceBouchilloux, Simone. Chlorination of L-tyrosine. Bulletin de la Societe de Chimie Biologique (1955), 37 255-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. Jasin HE: Oxidative modification of inflammatory synovial fluid immunoglobulin G. Inflammation. 1993 Apr;17(2):167-81. [8387962 ]
  3. Lamb NJ, Quinlan GJ, Westerman ST, Gutteridge JM, Evans TW: Nitration of proteins in bronchoalveolar lavage fluid from patients with acute respiratory distress syndrome receiving inhaled nitric oxide. Am J Respir Crit Care Med. 1999 Sep;160(3):1031-4. [10471637 ]
  4. Rosen H, Crowley JR, Heinecke JW: Human neutrophils use the myeloperoxidase-hydrogen peroxide-chloride system to chlorinate but not nitrate bacterial proteins during phagocytosis. J Biol Chem. 2002 Aug 23;277(34):30463-8. Epub 2002 Jun 11. [12060654 ]
  5. Kettle AJ: Detection of 3-chlorotyrosine in proteins exposed to neutrophil oxidants. Methods Enzymol. 1999;300:111-20. [9919515 ]
  6. Buss IH, Senthilmohan R, Darlow BA, Mogridge N, Kettle AJ, Winterbourn CC: 3-Chlorotyrosine as a marker of protein damage by myeloperoxidase in tracheal aspirates from preterm infants: association with adverse respiratory outcome. Pediatr Res. 2003 Mar;53(3):455-62. [12595594 ]
  7. Khan J, Brennand DM, Bradley N, Gao B, Bruckdorfer R, Jacobs M: 3-Nitrotyrosine in the proteins of human plasma determined by an ELISA method. Biochem J. 1998 Mar 1;330 ( Pt 2):795-801. [9480893 ]
  8. Mita H, Higashi N, Taniguchi M, Higashi A, Kawagishi Y, Akiyama K: Urinary 3-bromotyrosine and 3-chlorotyrosine concentrations in asthmatic patients: lack of increase in 3-bromotyrosine concentration in urine and plasma proteins in aspirin-induced asthma after intravenous aspirin challenge. Clin Exp Allergy. 2004 Jun;34(6):931-8. [15196282 ]
  9. Hazen SL, Heinecke JW: 3-Chlorotyrosine, a specific marker of myeloperoxidase-catalyzed oxidation, is markedly elevated in low density lipoprotein isolated from human atherosclerotic intima. J Clin Invest. 1997 May 1;99(9):2075-81. [9151778 ]