<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2015-06-11 10:46:25 -0600</creation_date>
  <update_date>2015-08-05 16:22:05 -0600</update_date>
  <accession>ECMDB23898</accession>
  <m2m_id>M2MDB005689</m2m_id>
  <name>L-Ornithine</name>
  <description>An optically active form of ornithine having L-configuration</description>
  <synonyms>
    <synonym>(S)-2,5-Diaminopentanoate</synonym>
    <synonym>(S)-2,5-Diaminopentanoic acid</synonym>
    <synonym>(S)-2,5-Diaminovalerate</synonym>
    <synonym>(S)-2,5-Diaminovaleric acid</synonym>
  </synonyms>
  <chemical_formula>C5H12N2O2</chemical_formula>
  <average_molecular_weight>132.161</average_molecular_weight>
  <monisotopic_moleculate_weight>132.089877638</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2,5-diaminopentanoic acid</iupac_name>
  <traditional_iupac>ornithine</traditional_iupac>
  <cas_registry_number>70-26-8</cas_registry_number>
  <smiles>NCCC[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1</inchi>
  <inchikey>AHLPHDHHMVZTML-BYPYZUCNSA-N</inchikey>
  <state/>
  <cellular_locations>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.72e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-3.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>2.67</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>10.29</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2S)-2,5-diaminopentanoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>132.161</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>132.089877638</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>NCCC[C@H](N)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C5H12N2O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>AHLPHDHHMVZTML-BYPYZUCNSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>89.34</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>33.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>13.85</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>3</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>
    <pathway>
      <name>Glutathione metabolism</name>
      <description>The biosynthesis of glutathione starts with the introduction of L-glutamic acid through either  a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a 
glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione.
This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione. 
</description>
      <pathwhiz_id>PW000833</pathwhiz_id>
      <kegg_map_id>ec00480</kegg_map_id>
      <subject>Metabolic</subject>
    </pathway>
    <pathway>
      <name>Arginine and proline metabolism</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00330</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Metabolic pathways</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>eco01100</kegg_map_id>
      <subject/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>130647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>138381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1054761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1054763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>166442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1212</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id>C00077</kegg_id>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <foodb_id/>
  <general_references>
  </general_references>
  <synthesis_reference/>
  <msds_url/>
  <enzymes>
    <enzyme>
      <name>Ornithine carbamoyltransferase chain I</name>
      <uniprot_id>P04391</uniprot_id>
      <uniprot_name>OTC1_ECOLI</uniprot_name>
      <gene_name>argI</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P04391.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Ornithine carbamoyltransferase chain F</name>
      <uniprot_id>P06960</uniprot_id>
      <uniprot_name>OTC2_ECOLI</uniprot_name>
      <gene_name>argF</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P06960.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Ornithine decarboxylase, constitutive</name>
      <uniprot_id>P21169</uniprot_id>
      <uniprot_name>DCOR_ECOLI</uniprot_name>
      <gene_name>speC</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P21169.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Acetylornithine deacetylase</name>
      <uniprot_id>P23908</uniprot_id>
      <uniprot_name>ARGE_ECOLI</uniprot_name>
      <gene_name>argE</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P23908.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Ornithine decarboxylase, inducible</name>
      <uniprot_id>P24169</uniprot_id>
      <uniprot_name>DCOS_ECOLI</uniprot_name>
      <gene_name>speF</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P24169.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
  </transporters>
  <reactions>
    <reaction_text>N-Acetylornithine + Water &lt;&gt; Acetic acid + Ornithine + L-Ornithine</reaction_text>
    <kegg_reaction_id>R00669</kegg_reaction_id>
    <ecocyc_id>ACETYLORNDEACET-RXN</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Carbamoylphosphate + Ornithine + L-Ornithine &lt;&gt; Citrulline + Hydrogen ion + Phosphate</reaction_text>
    <kegg_reaction_id>R01398</kegg_reaction_id>
    <ecocyc_id>ORNCARBAMTRANSFER-RXN</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Hydrogen ion + Ornithine + L-Ornithine &lt;&gt; Carbon dioxide + Putrescine + Ethylenediamine</reaction_text>
    <kegg_reaction_id>R00670</kegg_reaction_id>
    <ecocyc_id>ORNDECARBOX-RXN</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Carbamoylphosphate + Ornithine + L-Ornithine &lt;&gt; Citrulline + Hydrogen ion + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Hydrogen ion + Ornithine + L-Ornithine &lt;&gt; Carbon dioxide + Putrescine + Ethylenediamine</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>N-Acetylornithine + Water &lt;&gt; Acetic acid + Ornithine + L-Ornithine</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>N-Acetylornithine + Water &lt;&gt; Acetic acid + Ornithine + L-Ornithine</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
