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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-04-12 21:08:20 UTC
Update Date2019-07-23 05:47:08 UTC
HMDB IDHMDB0006045
Secondary Accession Numbers
  • HMDB06045
Metabolite Identification
Common NameDityrosine
DescriptionDityrosine is a fluorescent molecule formed as a result of normal posttranslational processing. In many structural proteins, dityrosine confers resistance to proteolysis and physicochemical trauma as a stabilizing crosslink. Dityrosine has also been found in oxidative/nitrative stress under a variety of conditions and biological systems. In this regard, it has been used as an important biomarker for oxidatively modified proteins during UV and gamma-irradiation, aging, and exposure to oxygen free radicals, nitrogen dioxide, peroxynitrite, and lipid hydroperoxides. Renewed interest in dityrosine and other tyrosine oxidation products as clinical indicators of oxidative modification has driven the development of important techniques for the specific analysis and quantification of these molecules. The presence of elevated levels of dityrosine in mammalian tissue and urine samples has been measured by chromatographic separation followed by mass spectrometry GC-MS and HPLC-MS/MS. Increases in dityrosine levels have been associated with pathologies such as eye cataracts, atherosclerosis, acute inflammation, and Alzheimer's disease. The continued development of, and increased accessibility to, improved mass spectrometric instrumentation will expand the capability, feasibility, and sensitivity with which specific biomarkers like dityrosine can be measured. (PMID: 17019703 ).
Structure
Data?1563860828
Synonyms
ValueSource
BityrosineHMDB
O,O'-dityrosineHMDB
O,O-DityrosineHMDB
2-Amino-3-[4'-(2-amino-2-carboxyethyl)-2,2'-dihydroxy-[1,1'-biphenyl]-4-yl]propanoateGenerator
Chemical FormulaC18H20N2O6
Average Molecular Weight360.3612
Monoisotopic Molecular Weight360.132136382
IUPAC Name2-amino-3-{4-[4-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3-hydroxyphenyl}propanoic acid
Traditional Name2-amino-3-{4-[4-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3-hydroxyphenyl}propanoic acid
CAS Registry Number980-21-2
SMILES
NC(CC1=CC(O)=C(C=C1)C1=CC=C(CC(N)C(O)=O)C=C1O)C(O)=O
InChI Identifier
InChI=1S/C18H20N2O6/c19-13(17(23)24)5-9-1-3-11(15(21)7-9)12-4-2-10(8-16(12)22)6-14(20)18(25)26/h1-4,7-8,13-14,21-22H,5-6,19-20H2,(H,23,24)(H,25,26)
InChI KeyFHOZGLMQYMAREG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassNot Available
Sub ClassNot Available
Direct ParentLignans, neolignans and related compounds
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • Neolignan skeleton
  • Biphenyl
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary aliphatic amine
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

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 Solubility0.052 g/LALOGPS
logP-2.8ALOGPS
logP-3.3ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
pKa (Strongest Basic)9.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area167.1 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity93.27 m³·mol⁻¹ChemAxon
Polarizability37.15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00r6-4094000000-69cfcedbb99c8bb8cb22Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0ff0-5100039000-cb3449936fc7a3cc50b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02t9-0039000000-ec7ae91410eca2c163aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0094000000-70dc4b0fd9a69a9afbb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0090000000-6bfa163a49d5227bf160Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-baf07a29301dbcc652a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-2529000000-229b9b59e584d12c9814Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-9811000000-f784f768398cc5e8fa4eSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.0052 +/- 0.00065 umol/mmol creatinineAdult (>18 years old)BothSmoking details
Associated Disorders and Diseases
Disease References
Smoking
  1. Orhan H, Coolen S, Meerman JH: Quantification of urinary o,o'-dityrosine, a biomarker for oxidative damage to proteins, by high performance liquid chromatography with triple quadrupole tandem mass spectrometry. A comparison with ion-trap tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Nov 15;827(1):104-8. [PubMed:15878312 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023818
KNApSAcK IDNot Available
Chemspider ID21233943
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477799
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Abdelrahim M, Morris E, Carver J, Facchina S, White A, Verma A: Liquid chromatographic assay of dityrosine in human cerebrospinal fluid. J Chromatogr B Biomed Sci Appl. 1997 Aug 29;696(2):175-82. [PubMed:9323538 ]
  2. Galeazzi L, Ronchi P, Franceschi C, Giunta S: In vitro peroxidase oxidation induces stable dimers of beta-amyloid (1-42) through dityrosine bridge formation. Amyloid. 1999 Mar;6(1):7-13. [PubMed:10211406 ]
  3. DiMarco T, Giulivi C: Current analytical methods for the detection of dityrosine, a biomarker of oxidative stress, in biological samples. Mass Spectrom Rev. 2007 Jan-Feb;26(1):108-20. [PubMed:17019703 ]