<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-08-15 08:51:30 -0600</creation_date>
  <update_date>2015-06-03 17:22:00 -0600</update_date>
  <accession>ECMDB21644</accession>
  <m2m_id>M2MDB002038</m2m_id>
  <name>2-Dehydro-3-deoxy-L-rhamnonate</name>
  <description>2-dehydro-3-deoxy-l-rhamnonate belongs to the class of Keto Fatty Acids. These are fatty acids containing a ketone group attached to the acyl chain.</description>
  <synonyms>
    <synonym>2-Dehydro-3,6-dideoxy-L-mannonate</synonym>
    <synonym>2-Dehydro-3,6-dideoxy-L-mannonic acid</synonym>
    <synonym>2-Dehydro-3-deoxy-L-rhamnonate</synonym>
    <synonym>2-Dehydro-3-deoxy-L-rhamnonic acid</synonym>
    <synonym>3,6-Dideoxy-L-arabino-hex-2-ulosonate</synonym>
    <synonym>3,6-Dideoxy-L-arabino-hex-2-ulosonic acid</synonym>
  </synonyms>
  <chemical_formula>C6H10O5</chemical_formula>
  <average_molecular_weight>162.1406</average_molecular_weight>
  <monisotopic_moleculate_weight>162.05282343</monisotopic_moleculate_weight>
  <iupac_name>(4R,5S)-4,5-dihydroxy-2-oxohexanoic acid</iupac_name>
  <traditional_iupac>(4R,5S)-4,5-dihydroxy-2-oxohexanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@](C)(O)[C@]([H])(O)CC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H10O5/c1-3(7)4(8)2-5(9)6(10)11/h3-4,7-8H,2H2,1H3,(H,10,11)/t3-,4+/m0/s1</inchi>
  <inchikey>FRIWJYNKZPJVRL-IUYQGCFVSA-N</inchikey>
  <state/>
  <cellular_locations>
    <cellular_location>Cytoplasm</cellular_location>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.19e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-0.73</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>3.06</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(4R,5S)-4,5-dihydroxy-2-oxohexanoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>162.1406</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>162.05282343</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>[H][C@@](C)(O)[C@]([H])(O)CC(=O)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C6H10O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C6H10O5/c1-3(7)4(8)2-5(9)6(10)11/h3-4,7-8H,2H2,1H3,(H,10,11)/t3-,4+/m0/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>FRIWJYNKZPJVRL-IUYQGCFVSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>94.83</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>34.77</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>14.59</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</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>Fructose and mannose metabolism</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00051</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>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1083610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32200</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id>49852300</pubchem_compound_id>
  <chemspider_id>26331139</chemspider_id>
  <kegg_id>C03979</kegg_id>
  <chebi_id>18078</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <foodb_id/>
  <general_references>
    <reference>
      <reference_text>Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A</reference_text>
      <pubmed_id/>
    </reference>
  </general_references>
  <synthesis_reference/>
  <msds_url/>
  <enzymes>
    <enzyme>
      <name>2-keto-3-deoxy-L-rhamnonate aldolase</name>
      <uniprot_id>P76469</uniprot_id>
      <uniprot_name>RHMA_ECOLI</uniprot_name>
      <gene_name>rhmA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P76469.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>L-rhamnonate dehydratase</name>
      <uniprot_id>P77215</uniprot_id>
      <uniprot_name>RHMD_ECOLI</uniprot_name>
      <gene_name>rhmD</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P77215.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
  </transporters>
  <reactions>
    <reaction_text>2-Dehydro-3-deoxy-L-rhamnonate &lt;&gt; Lactaldehyde + Pyruvic acid + (S)-Lactaldehyde</reaction_text>
    <kegg_reaction_id>R02261</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>L-Rhamnonate + L-Rhamnonate &lt;&gt; 2-Dehydro-3-deoxy-L-rhamnonate + Water</reaction_text>
    <kegg_reaction_id>R03774</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>2-Dehydro-3-deoxy-L-rhamnonate &gt; Pyruvic acid + D-Lactaldehyde</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>L-Rhamnonate &gt; 2-Dehydro-3-deoxy-L-rhamnonate + Water</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>2 2-Dehydro-3-deoxy-L-rhamnonate &lt;&gt; Lactaldehyde + Pyruvic acid + (S)-Lactaldehyde</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
