<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:14:05 UTC</creation_date>
  <update_date>2019-11-26 03:16:59 UTC</update_date>
  <accession>FDB019015</accession>
  <name>N2-gamma-L-Glutamyl-L-ornithine</name>
  <description>Constituent of the edible shiitake mushroom (Lentinus edodes)

Found in human urine. - PubMed reference: 1148212; ; Gamma-glutamylornithine has been identified in urine from patients with the HHH syndrome (hyperornithinemia, hyperammonemia and homocitrullinuria) and with gyrate atrophy associated with hyperornithinemia. The amount of gamma-glutamylornithine excreted was 10-15 times higher than that excreted in normal subjects. - PubMed reference: 6547887</description>
  <synonyms>
    <synonym>Gamma glutamyl ornithine</synonym>
    <synonym>Gamma-glu-orn</synonym>
    <synonym>Gamma-glutamylornithine</synonym>
    <synonym>L-gamma-glutamyl-l-ornithine</synonym>
    <synonym>L-Ornithine, N2-L-gamma-glutamyl-, stereoisomer</synonym>
  </synonyms>
  <chemical_formula>C10H19N3O5</chemical_formula>
  <average_molecular_weight>261.275</average_molecular_weight>
  <monisotopic_moleculate_weight>261.132470733</monisotopic_moleculate_weight>
  <iupac_name>2-amino-4-[(4-amino-1-carboxybutyl)-C-hydroxycarbonimidoyl]butanoic acid</iupac_name>
  <traditional_iupac>2-amino-4-[(4-amino-1-carboxybutyl)-C-hydroxycarbonimidoyl]butanoic acid</traditional_iupac>
  <cas_registry_number>56523-61-6</cas_registry_number>
  <smiles>NCCCC(NC(=O)CCC(N)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C10H19N3O5/c11-5-1-2-7(10(17)18)13-8(14)4-3-6(12)9(15)16/h6-7H,1-5,11-12H2,(H,13,14)(H,15,16)(H,17,18)</inchi>
  <inchikey>BBAYFIRFVORJLJ-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>Aliphatic acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Alpha amino acids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</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>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</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>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</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>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>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-4.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.92e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 209°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-5.8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>1.94</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>10.29</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-amino-4-[(4-amino-1-carboxybutyl)-C-hydroxycarbonimidoyl]butanoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>261.275</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>261.132470733</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>NCCCC(NC(=O)CCC(N)C(O)=O)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H19N3O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H19N3O5/c11-5-1-2-7(10(17)18)13-8(14)4-3-6(12)9(15)16/h6-7H,1-5,11-12H2,(H,13,14)(H,15,16)(H,17,18)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>BBAYFIRFVORJLJ-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>159.23</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>61.82</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>26.09</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</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>86283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>86284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>86285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>148548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>148549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>148550</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB02248</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:0x000055ce30f70158&gt;</reference>
    <reference>#&lt;Reference:0x000055ce30f6ff50&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Common mushroom</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Agaricus bisporus</name_scientific>
      <ncbi_taxonomy_id>5341</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mushrooms</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Oyster mushroom</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Pleurotus ostreatus</name_scientific>
      <ncbi_taxonomy_id>5322</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
