1.02011-09-21 00:35:16 UTC2015-07-21 06:57:53 UTCFDB023818DityrosineDityrosine 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) [HMDB]BityrosineO,o-dityrosineo,o'-dityrosineC18H20N2O6360.3612360.1321363822-amino-3-{4-[4-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3-hydroxyphenyl}propanoic acid2-amino-3-{4-[4-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3-hydroxyphenyl}propanoic acid980-21-2NC(CC1=CC(O)=C(C=C1)C1=CC=C(CC(N)C(O)=O)C=C1O)C(O)=OInChI=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)FHOZGLMQYMAREG-UHFFFAOYSA-N 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 C9ยด 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.Lignans, neolignans and related compoundsOrganic compoundsLignans, neolignans and related compoundsAromatic homomonocyclic compounds1-hydroxy-2-unsubstituted benzenoids1-hydroxy-4-unsubstituted benzenoidsAlpha amino acidsAmino acidsAmphetamines and derivativesAralkylaminesBiphenyls and derivativesCarbonyl compoundsCarboxylic acidsDicarboxylic acids and derivativesHydrocarbon derivativesMonoalkylaminesOrganic oxidesOrganopnictogen compoundsPhenylalanine and derivativesPhenylpropanoic acids1-hydroxy-2-unsubstituted benzenoid1-hydroxy-4-unsubstituted benzenoid3-phenylpropanoic-acidAlpha-amino acidAlpha-amino acid or derivativesAmineAmino acidAmino acid or derivativesAmphetamine or derivativesAralkylamineAromatic homomonocyclic compoundBenzenoidBiphenylCarbonyl groupCarboxylic acidCarboxylic acid derivativeDicarboxylic acid or derivativesHydrocarbon derivativeMonocyclic benzene moietyNeolignan skeletonOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhenolPhenylalanine or derivativesPrimary aliphatic aminePrimary amineSolidlogp-2.78logs-3.84solubility5.16e-02 g/llogp-3.3pka_strongest_acidic1.56pka_strongest_basic9.94iupac2-amino-3-{4-[4-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3-hydroxyphenyl}propanoic acidaverage_mass360.3612mono_mass360.132136382smilesNC(CC1=CC(O)=C(C=C1)C1=CC=C(CC(N)C(O)=O)C=C1O)C(O)=OformulaC18H20N2O6inchiInChI=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)inchikeyFHOZGLMQYMAREG-UHFFFAOYSA-Npolar_surface_area167.1refractivity93.27polarizability37.15rotatable_bond_count7acceptor_count8donor_count6physiological_charge0formal_charge0Specdb::CMs15180Specdb::CMs38947Specdb::CMs152850Specdb::MsMs67995Specdb::MsMs67996Specdb::MsMs67997Specdb::MsMs125937Specdb::MsMs125938Specdb::MsMs125939Specdb::MsMs2771189Specdb::MsMs2771190Specdb::MsMs2771191Specdb::MsMs2907801Specdb::MsMs2907802Specdb::MsMs2907803Specdb::NmrOneD150100Specdb::NmrOneD150101Specdb::NmrOneD150102Specdb::NmrOneD150103Specdb::NmrOneD150104Specdb::NmrOneD150105Specdb::NmrOneD150106Specdb::NmrOneD150107Specdb::NmrOneD150108Specdb::NmrOneD150109Specdb::NmrOneD150110Specdb::NmrOneD150111Specdb::NmrOneD150112Specdb::NmrOneD150113Specdb::NmrOneD150114Specdb::NmrOneD150115Specdb::NmrOneD150116Specdb::NmrOneD150117Specdb::NmrOneD150118Specdb::NmrOneD150119HMDB06045#<Reference:0x0000555675ca58c0>#<Reference:0x0000555675ca5708>#<Reference:0x0000555675ca5550>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823