<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-05-31 14:01:37 -0600</creation_date>
  <update_date>2015-07-14 14:32:03 -0600</update_date>
  <accession>ECMDB03974</accession>
  <m2m_id>M2MDB000548</m2m_id>
  <name>Oxalosuccinic acid</name>
  <description>Oxalosuccinate is a substrate for cytoplasmic Isocitrate dehydrogenase  and mitochondiral Isocitrate dehydrogenase (mitochondrial).</description>
  <synonyms>
    <synonym>Oxalo-succ</synonym>
    <synonym>Oxalosuccinate</synonym>
    <synonym>Oxalosuccinic acid</synonym>
  </synonyms>
  <chemical_formula>C6H6O7</chemical_formula>
  <average_molecular_weight>190.1076</average_molecular_weight>
  <monisotopic_moleculate_weight>190.011352546</monisotopic_moleculate_weight>
  <iupac_name>1-oxopropane-1,2,3-tricarboxylic acid</iupac_name>
  <traditional_iupac>oxalosuccinate</traditional_iupac>
  <cas_registry_number>1948-82-9</cas_registry_number>
  <smiles>OC(=O)CC(C(O)=O)C(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H6O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2H,1H2,(H,7,8)(H,10,11)(H,12,13)</inchi>
  <inchikey>UFSCUAXLTRFIDC-UHFFFAOYSA-N</inchikey>
  <state>Solid</state>
  <cellular_locations>
    <cellular_location>Cytoplasm</cellular_location>
    <cellular_location>Periplasm</cellular_location>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.47e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-0.37</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>2.38</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-10</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>1-oxopropane-1,2,3-tricarboxylic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>190.1076</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>190.011352546</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC(=O)CC(C(O)=O)C(=O)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C6H6O7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C6H6O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2H,1H2,(H,7,8)(H,10,11)(H,12,13)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>UFSCUAXLTRFIDC-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>128.97</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>35.17</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>14.95</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-3</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>Citrate cycle (TCA cycle)</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00020</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Reductive carboxylate cycle (CO2 fixation)</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00720</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Microbial metabolism in diverse environments</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec01120</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>3033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>288654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3608797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3608798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3608799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3608800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3608801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3608802</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB03974</hmdb_id>
  <pubchem_compound_id>972</pubchem_compound_id>
  <chemspider_id/>
  <kegg_id>C05379</kegg_id>
  <chebi_id/>
  <biocyc_id>OXALO-SUCCINATE</biocyc_id>
  <het_id/>
  <wikipidia>Oxalosuccinic_acid</wikipidia>
  <foodb_id/>
  <general_references>
    <reference>
      <reference_text>Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.</reference_text>
      <pubmed_id>21097882</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.</reference_text>
      <pubmed_id>22080510</pubmed_id>
    </reference>
  </general_references>
  <synthesis_reference>Takeda, Isao; Iguchi, Takashi.  Fermentative production of oxalosuccinic acid from hydrocarbons.    Jpn. Tokkyo Koho  (1972),     3 pp.</synthesis_reference>
  <msds_url/>
  <enzymes>
    <enzyme>
      <name>Isocitrate dehydrogenase [NADP]</name>
      <uniprot_id>P08200</uniprot_id>
      <uniprot_name>IDH_ECOLI</uniprot_name>
      <gene_name>icd</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P08200.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
  </transporters>
  <reactions>
    <reaction_text>Oxalosuccinic acid &lt;&gt; alpha-Ketoglutarate + Carbon dioxide</reaction_text>
    <kegg_reaction_id>R00268</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Isocitric acid + NADP &lt;&gt; Oxalosuccinic acid + NADPH + Hydrogen ion</reaction_text>
    <kegg_reaction_id>R01899</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Oxalosuccinic acid + Hydrogen ion &gt; Oxoglutaric acid + Carbon dioxide</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>RXN-8642</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Isocitric acid + NADP &gt; Oxalosuccinic acid + NADPH + Hydrogen ion</reaction_text>
    <kegg_reaction_id>R01899</kegg_reaction_id>
    <ecocyc_id>RXN-9951</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Isocitric acid + NADP + Oxalosuccinic acid &lt;&gt; alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ion</reaction_text>
    <kegg_reaction_id>R00267 </kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
