<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:04:41 UTC</creation_date>
  <update_date>2019-11-26 02:55:16 UTC</update_date>
  <accession>FDB000717</accession>
  <name>N-gamma-L-Glutamyl-L-tyrosine</name>
  <description>Isolated from the seeds of Glycine max (soybean)

Gamma-Glutamyltyrosine is made of glutamic acid and tyrosine. o-Tyrosine is a normal human metabolite. Its presence is possible due to the hydroxylation of l-phenylalanine by hydroxyl radical (*OH), and is proposed as an  hydroxy radical biomarker of oxidative damage to proteins. o-Tyrosine might also be included in the diet and absorbed. It has been associated with disease such as Kwashiorkor, a severe form of protein-energy malnutrition. However, many publications mention that the results are inconclusive, and o-tyrosine is not selectively altered by antioxidant intervention, exercise training or age. (PMID: 14670743, 10969271, 9887186). N-gamma-L-Glutamyl-L-tyrosine is found in pulses.</description>
  <synonyms>
    <synonym>g-Glutamyltyrosine</synonym>
    <synonym>Gamma-glutamyltyrosine</synonym>
    <synonym>N-l-gamma-glutamyl-l-tyrosine</synonym>
    <synonym>γ-glutamyltyrosine</synonym>
  </synonyms>
  <chemical_formula>C14H18N2O6</chemical_formula>
  <average_molecular_weight>310.3025</average_molecular_weight>
  <monisotopic_moleculate_weight>310.116486318</monisotopic_moleculate_weight>
  <iupac_name>2-amino-4-{[1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}butanoic acid</iupac_name>
  <traditional_iupac>2-amino-4-{[1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}butanoic acid</traditional_iupac>
  <cas_registry_number>7432-23-7</cas_registry_number>
  <smiles>NC(CCC(=O)NC(CC1=CC=C(O)C=C1)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C14H18N2O6/c15-10(13(19)20)5-6-12(18)16-11(14(21)22)7-8-1-3-9(17)4-2-8/h1-4,10-11,17H,5-7,15H2,(H,16,18)(H,19,20)(H,21,22)</inchi>
  <inchikey>VVLXCWVSSLFQDS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.</description>
    <direct_parent>Dipeptides</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alpha amino acids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Gamma-glutamyl amino acids</alternative_parent>
      <alternative_parent>Glutamine and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalanine and derivatives</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tyrosine and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-dipeptide</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Gamma-glutamyl alpha-amino acid</substituent>
      <substituent>Glutamine or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tyrosine or derivatives</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>9.87e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 221-222° dec.</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-2.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>1.81</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>9.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-amino-4-{[1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}butanoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>310.3025</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>310.116486318</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>NC(CCC(=O)NC(CC1=CC=C(O)C=C1)C(O)=O)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C14H18N2O6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C14H18N2O6/c15-10(13(19)20)5-6-12(18)16-11(14(21)22)7-8-1-3-9(17)4-2-8/h1-4,10-11,17H,5-7,15H2,(H,16,18)(H,19,20)(H,21,22)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>VVLXCWVSSLFQDS-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>149.95</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>75.18</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>30.63</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>150900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>150901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>150902</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB11741</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce31e530a8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31e52ef0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31e52d38&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Pulses</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
