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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-28 10:36:16 UTC
Update Date2021-09-14 15:20:03 UTC
HMDB IDHMDB0001885
Secondary Accession Numbers
  • HMDB01885
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
3-Chlorotyrosine, (L)-isomerHMDB
3-Chlorotyrosine hydrochloride, (L)-isomerHMDB
2-Amino-3-(3-chloro-4-hydroxyphenyl)propanoateHMDB
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 KeyACWBBAGYTKWBCD-UHFFFAOYSA-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
  • 2-chlorophenol
  • 2-halophenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Halobenzene
  • Chlorobenzene
  • Phenol
  • Aralkylamine
  • Aryl halide
  • Benzenoid
  • Aryl chloride
  • Monocyclic benzene moiety
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organohalogen compound
  • Primary aliphatic amine
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Leukocyte
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified6.96 +/- 3.578 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified0.0007 +/- 0.0005 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
    • Analysis of 30 no...
details
UrineDetected and Quantified0.0023 +/- 0.0016 umol/mmol creatinineAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease References
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. [PubMed:17512353 ]
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. [PubMed:15196282 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022723
KNApSAcK IDNot Available
Chemspider ID106510
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6369
PubChem Compound119226
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000351
Good Scents 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)Not Available
General References