1.0 2011-09-21 00:35:16 UTC 2015-07-21 06:57:53 UTC FDB023818 Dityrosine Dityrosine 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] Bityrosine O,o-dityrosine o,o'-dityrosine C18H20N2O6 360.3612 360.132136382 2-amino-3-{4-[4-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3-hydroxyphenyl}propanoic acid 2-amino-3-{4-[4-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3-hydroxyphenyl}propanoic acid 980-21-2 NC(CC1=CC(O)=C(C=C1)C1=CC=C(CC(N)C(O)=O)C=C1O)C(O)=O 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) 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 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. Lignans, neolignans and related compounds Organic compounds Lignans, neolignans and related compounds Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alpha amino acids Amino acids Amphetamines and derivatives Aralkylamines Biphenyls and derivatives Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds Phenylalanine and derivatives Phenylpropanoic acids 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3-phenylpropanoic-acid Alpha-amino acid Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Amphetamine or derivatives Aralkylamine Aromatic homomonocyclic compound Benzenoid Biphenyl Carbonyl group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Hydrocarbon derivative Monocyclic benzene moiety Neolignan skeleton Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol Phenylalanine or derivatives Primary aliphatic amine Primary amine Solid logp -2.78 ALOGPS logs -3.84 ALOGPS solubility 5.16e-02 g/l ALOGPS logp -3.3 ChemAxon pka_strongest_acidic 1.56 ChemAxon pka_strongest_basic 9.94 ChemAxon iupac 2-amino-3-{4-[4-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3-hydroxyphenyl}propanoic acid ChemAxon average_mass 360.3612 ChemAxon mono_mass 360.132136382 ChemAxon smiles NC(CC1=CC(O)=C(C=C1)C1=CC=C(CC(N)C(O)=O)C=C1O)C(O)=O ChemAxon formula C18H20N2O6 ChemAxon inchi 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) ChemAxon inchikey FHOZGLMQYMAREG-UHFFFAOYSA-N ChemAxon polar_surface_area 167.1 ChemAxon refractivity 93.27 ChemAxon polarizability 37.15 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 15180 Specdb::CMs 38947 Specdb::CMs 152850 Specdb::MsMs 67995 Specdb::MsMs 67996 Specdb::MsMs 67997 Specdb::MsMs 125937 Specdb::MsMs 125938 Specdb::MsMs 125939 Specdb::MsMs 2771189 Specdb::MsMs 2771190 Specdb::MsMs 2771191 Specdb::MsMs 2907801 Specdb::MsMs 2907802 Specdb::MsMs 2907803 Specdb::NmrOneD 150100 Specdb::NmrOneD 150101 Specdb::NmrOneD 150102 Specdb::NmrOneD 150103 Specdb::NmrOneD 150104 Specdb::NmrOneD 150105 Specdb::NmrOneD 150106 Specdb::NmrOneD 150107 Specdb::NmrOneD 150108 Specdb::NmrOneD 150109 Specdb::NmrOneD 150110 Specdb::NmrOneD 150111 Specdb::NmrOneD 150112 Specdb::NmrOneD 150113 Specdb::NmrOneD 150114 Specdb::NmrOneD 150115 Specdb::NmrOneD 150116 Specdb::NmrOneD 150117 Specdb::NmrOneD 150118 Specdb::NmrOneD 150119 HMDB06045 #<Reference:0x00007f08ff156cd8> #<Reference:0x00007f08ff156b20> #<Reference:0x00007f08ff1568f0> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823