<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-05-31 14:04:10 -0600</creation_date>
  <update_date>2015-10-15 16:14:30 -0600</update_date>
  <accession>ECMDB04069</accession>
  <m2m_id>M2MDB000595</m2m_id>
  <name>L-Fuculose</name>
  <description>L-fuculose is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose.  Fuculose or 6-deoxy-tagatose is a ketohexose deoxy sugar. (WikiPedia)</description>
  <synonyms>
    <synonym>6-Deoxy-L-lyxo-hex-2-ulose</synonym>
    <synonym>6-Deoxy-L-tagatose</synonym>
    <synonym>Fuculose</synonym>
  </synonyms>
  <chemical_formula>C6H12O5</chemical_formula>
  <average_molecular_weight>164.157</average_molecular_weight>
  <monisotopic_moleculate_weight>164.068473486</monisotopic_moleculate_weight>
  <iupac_name>(3R,4R,5S)-1,3,4,5-tetrahydroxyhexan-2-one</iupac_name>
  <traditional_iupac>L-fuculose</traditional_iupac>
  <cas_registry_number>2438-80-4</cas_registry_number>
  <smiles>CC(O)C(O)C(O)C(=O)CO</smiles>
  <inchi>InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h3,5-8,10-11H,2H2,1H3</inchi>
  <inchikey>QZNPNKJXABGCRC-UHFFFAOYSA-N</inchikey>
  <state></state>
  <cellular_locations>
    <cellular_location>Cytosol</cellular_location>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.88e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>150 - 153</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-2.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>10.47</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(3R,4R,5S)-1,3,4,5-tetrahydroxyhexan-2-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>164.157</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>164.068473486</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(O)C(O)C(O)C(=O)CO</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C6H12O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h3,5-8,10-11H,2H2,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>QZNPNKJXABGCRC-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>97.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>36.02</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>15.48</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>4</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>
    <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>
    <pathway>
      <name>fucose degradation</name>
      <ecocyc_pathway_id>FUCCAT-PWY</ecocyc_pathway_id>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>35550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>48113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>161385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3224926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3224927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3224928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3224929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3224930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3224931</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id>6857362</pubchem_compound_id>
  <chemspider_id>5256704</chemspider_id>
  <kegg_id>C01721</kegg_id>
  <chebi_id>17617</chebi_id>
  <biocyc_id>L-FUCULOSE</biocyc_id>
  <het_id/>
  <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>
    <reference>
      <reference_text>van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.</reference_text>
      <pubmed_id>17765195</pubmed_id>
    </reference>
    <reference>
      <reference_text>Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.</reference_text>
      <pubmed_id>18331064</pubmed_id>
    </reference>
  </general_references>
  <synthesis_reference></synthesis_reference>
  <msds_url/>
  <enzymes>
    <enzyme>
      <name>L-fuculokinase</name>
      <uniprot_id>P11553</uniprot_id>
      <uniprot_name>FUCK_ECOLI</uniprot_name>
      <gene_name>fucK</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P11553.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>L-fucose isomerase</name>
      <uniprot_id>P69922</uniprot_id>
      <uniprot_name>FUCI_ECOLI</uniprot_name>
      <gene_name>fucI</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P69922.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
    <enzyme>
      <name>Sugar efflux transporter C</name>
      <uniprot_id>P31436</uniprot_id>
      <uniprot_name>SETC_ECOLI</uniprot_name>
      <gene_name>setC</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P31436.xml</protein_url>
    </enzyme>
  </transporters>
  <reactions>
    <reaction_text>L-Fucose &lt;&gt; L-Fuculose</reaction_text>
    <kegg_reaction_id>R03163</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + L-Fuculose &lt;&gt; ADP + L-Fuculose 1-phosphate + Hydrogen ion</reaction_text>
    <kegg_reaction_id>R03241</kegg_reaction_id>
    <ecocyc_id>FUCULOKIN-RXN</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + L-Fuculose &lt;&gt; ADP + L-Fuculose 1-phosphate</reaction_text>
    <kegg_reaction_id>R03241</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>L-fucose &lt;&gt; L-Fuculose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>FUCISOM-RXN</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>L-Fuculose + Adenosine triphosphate &gt; Hydrogen ion + L-Fuculose 1-phosphate + ADP</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>FUCULOKIN-RXN</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>L-Fucose &gt; L-Fuculose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + L-Fuculose &gt; ADP + L-Fuculose 1-phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
