<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:15:06 UTC</creation_date>
  <update_date>2019-11-26 03:19:06 UTC</update_date>
  <accession>FDB020543</accession>
  <name>L-Fucose</name>
  <description>A constituent of the polysaccharides obtained from gum tragacanthand is) also found in glycoproteins obtained from milk

Fucose is a hexose deoxy sugar with the chemical formula C6H12O5. It is found on N-linked glycans on the mammalian, insect and plant cell surface, and is the fundamental sub-unit of the fucoidan polysaccharide. Alpha1?3 linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy.; Fucose is a hexose sugar with the chemical formula C6H12O5. It is found on N-linked glycans on the mammalian and plant cell surface. Fucose is secreted in urine when the liver is damaged.  Alpha1-&gt;3 linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy.  Two structural features distinguish fucose from other six-carbon sugars present in mammals: the lack of a hydroxyl group on the carbon at the 6-position (C-6) and the L-configuration. In fucose-containing glycan structures, fucosylated glycans, fucose can exist as a terminal modification or serve as an attachment point for adding other sugars.</description>
  <synonyms>
    <synonym>(-)-fucose</synonym>
    <synonym>(-)-l-fucose</synonym>
    <synonym>6-Deoxy-beta-galactose</synonym>
    <synonym>6-Deoxy-D-galactopyranose</synonym>
    <synonym>6-Deoxy-delta-galactopyranose</synonym>
    <synonym>6-Deoxy-L-beta-galactose</synonym>
    <synonym>6-Deoxy-L-galactopyranose</synonym>
    <synonym>6-Deoxy-L-galactose</synonym>
    <synonym>6-Desoxygalactose</synonym>
    <synonym>6-methyloxane-2,3,4,5-tetrol</synonym>
    <synonym>6-methyltetrahydropyran-2,3,4,5-tetraol</synonym>
    <synonym>D-threo-aldose</synonym>
    <synonym>FUC</synonym>
    <synonym>Fucopyranose, L- (7CI)</synonym>
    <synonym>Fucose</synonym>
    <synonym>Fucose, l-</synonym>
    <synonym>L-(-)-fucose</synonym>
    <synonym>L-fucopyranose</synonym>
    <synonym>L-fucose</synonym>
    <synonym>L-galactomethylose</synonym>
    <synonym>L-galactopyranose, 6-deoxy-</synonym>
    <synonym>L-Galactopyranose, 6-deoxy- (9CI)</synonym>
    <synonym>L-Galactose, 6-deoxy-</synonym>
    <synonym>Rhodeose</synonym>
  </synonyms>
  <chemical_formula>C18H36O15</chemical_formula>
  <average_molecular_weight>492.4694</average_molecular_weight>
  <monisotopic_moleculate_weight>492.205420482</monisotopic_moleculate_weight>
  <iupac_name>(3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>L-fucose</traditional_iupac>
  <cas_registry_number>2438-80-4</cas_registry_number>
  <smiles>CC(O)C(O)C(O)C(O)C=O.CC(O)C1OC(O)C(O)C1O.CC1OC(O)C(O)C(O)C1O</smiles>
  <inchi>InChI=1S/3C6H12O5/c1-2(7)5-3(8)4(9)6(10)11-5;1-2-3(7)4(8)5(9)6(10)11-2;1-3(8)5(10)6(11)4(9)2-7/h2*2-10H,1H3;2-6,8-11H,1H3</inchi>
  <inchikey>LSOFIIQFGYOXNZ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <direct_parent>Hexoses</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Deoxy sugars</external_descriptor>
      <external_descriptor>L-fucose</external_descriptor>
      <external_descriptor>fucopyranose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 145° (140-141°)</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-1.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>11.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>492.4694</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>492.205420482</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(O)C(O)C(O)C(O)C=O.CC(O)C1OC(O)C(O)C1O.CC1OC(O)C(O)C(O)C1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C18H36O15</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/3C6H12O5/c1-2(7)5-3(8)4(9)6(10)11-5;1-2-3(7)4(8)5(9)6(10)11-2;1-3(8)5(10)6(11)4(9)2-7/h2*2-10H,1H3;2-6,8-11H,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>LSOFIIQFGYOXNZ-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>90.15</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>34.38</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>15.35</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</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 Degradation</name>
      <smpdb_id>SMP00064</smpdb_id>
      <kegg_map_id>map00051</kegg_map_id>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>166520</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB00174</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>18287</chebi_id>
  <biocyc_id/>
  <het_id>1AH1</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce32509938&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32509780&gt;</reference>
    <reference>#&lt;Reference:0x000055ce325095c8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32509410&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32509258&gt;</reference>
    <reference>#&lt;Reference:0x000055ce325090a0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32508ee8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32508d30&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32508b78&gt;</reference>
    <reference>#&lt;Reference:0x000055ce325089c0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32508808&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32508650&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32508498&gt;</reference>
    <reference>#&lt;Reference:0x000055ce325082e0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32508128&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32507f48&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32507d90&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32507bd8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce325079f8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32507818&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32507660&gt;</reference>
    <reference>#&lt;Reference:0x000055ce325074a8&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Anatidae</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anatidae</name_scientific>
      <ncbi_taxonomy_id>8830</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Beefalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus X Bison bison</name_scientific>
      <ncbi_taxonomy_id>297284</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Bison</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bison bison</name_scientific>
      <ncbi_taxonomy_id>9901</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Buffalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bubalus bubalis</name_scientific>
      <ncbi_taxonomy_id>89462</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Caraway</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Carum carvi</name_scientific>
      <ncbi_taxonomy_id>48032</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cattle (Beef, Veal)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus</name_scientific>
      <ncbi_taxonomy_id>9913</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Chicken</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Gallus gallus</name_scientific>
      <ncbi_taxonomy_id>9031</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Columbidae (Dove, Pigeon)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columbidae</name_scientific>
      <ncbi_taxonomy_id>8930</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Corn</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zea mays</name_scientific>
      <ncbi_taxonomy_id>4577</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervidae</name_scientific>
      <ncbi_taxonomy_id>9850</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic goat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capra aegagrus hircus</name_scientific>
      <ncbi_taxonomy_id>9925</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic pig</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa domestica</name_scientific>
      <ncbi_taxonomy_id>9825</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Elk</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervus canadensis</name_scientific>
      <ncbi_taxonomy_id>1574408</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Emu</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Dromaius novaehollandiae</name_scientific>
      <ncbi_taxonomy_id>8790</ncbi_taxonomy_id>
    </food>
    <food>
      <name>European rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryctolagus</name_scientific>
      <ncbi_taxonomy_id>9984</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Flaxseed</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Linum usitatissimum</name_scientific>
      <ncbi_taxonomy_id>4006</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Garden tomato</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Solanum lycopersicum</name_scientific>
      <ncbi_taxonomy_id>4081</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Grape wine</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
      <average_value>0.0</average_value>
      <max_value>0.0</max_value>
      <min_value>0.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Greylag goose</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anser anser</name_scientific>
      <ncbi_taxonomy_id>8843</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Guinea hen</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Numida meleagris</name_scientific>
      <ncbi_taxonomy_id>8996</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Horse</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Equus caballus</name_scientific>
      <ncbi_taxonomy_id>9796</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mallard duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anas platyrhynchos</name_scientific>
      <ncbi_taxonomy_id>8839</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Milk (Cow)</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>26.016364</average_value>
      <max_value>35.0</max_value>
      <min_value>15.36</min_value>
      <unit>uM</unit>
    </food>
    <food>
      <name>Milk and milk products</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Mountain hare</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lepus timidus</name_scientific>
      <ncbi_taxonomy_id>62621</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mule deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Odocoileus</name_scientific>
      <ncbi_taxonomy_id>9871</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mung bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Vigna radiata</name_scientific>
      <ncbi_taxonomy_id>157791</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Ostrich</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Struthio camelus</name_scientific>
      <ncbi_taxonomy_id>8801</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pheasant</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianus colchicus</name_scientific>
      <ncbi_taxonomy_id>9054</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Potato</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Solanum tuberosum</name_scientific>
      <ncbi_taxonomy_id>4113</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Quail</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianidae</name_scientific>
      <ncbi_taxonomy_id>9005</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Leporidae</name_scientific>
      <ncbi_taxonomy_id>9979</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rock ptarmigan</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lagopus muta</name_scientific>
      <ncbi_taxonomy_id>64668</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sheep (Mutton, Lamb)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ovis aries</name_scientific>
      <ncbi_taxonomy_id>9940</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Squab</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columba</name_scientific>
      <ncbi_taxonomy_id>8931</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Turkey</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Meleagris gallopavo</name_scientific>
      <ncbi_taxonomy_id>9103</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Velvet duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Melanitta fusca</name_scientific>
      <ncbi_taxonomy_id>371864</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild boar</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa</name_scientific>
      <ncbi_taxonomy_id>9823</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Acetylcholinesterase</name>
      <uniprot_id>P22303</uniprot_id>
      <uniprot_name/>
      <gene_name>ACHE</gene_name>
    </enzyme>
    <enzyme>
      <name>L-fucose kinase</name>
      <uniprot_id>Q8N0W3</uniprot_id>
      <uniprot_name/>
      <gene_name>FUK</gene_name>
    </enzyme>
    <enzyme>
      <name>Plasma alpha-L-fucosidase</name>
      <uniprot_id>Q9BTY2</uniprot_id>
      <uniprot_name/>
      <gene_name>FUCA2</gene_name>
    </enzyme>
    <enzyme>
      <name>Tissue alpha-L-fucosidase</name>
      <uniprot_id>P04066</uniprot_id>
      <uniprot_name/>
      <gene_name>FUCA1</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
