<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:18 UTC</creation_date>
  <update_date>2020-05-21 16:28:33 UTC</update_date>
  <accession>BMDB0001265</accession>
  <secondary_accessions>
    <accession>BMDB01265</accession>
  </secondary_accessions>
  <name>Fucose 1-phosphate</name>
  <description>Fucose 1-phosphate belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Fucose 1-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Fucose 1-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Fucose 1-phosphate can be converted into GDP-L-fucose; which is catalyzed by the enzyme fucose-1-phosphate guanylyltransferase. In addition, Fucose 1-phosphate can be biosynthesized from L-fucose through its interaction with the enzyme L-fucose kinase. In cattle, fucose 1-phosphate is involved in the metabolic pathway called the fructose and mannose degradation pathway.</description>
  <synonyms>
    <synonym>6-Deoxy-1-O-phosphono-L-galactopyranose</synonym>
    <synonym>6-Deoxy-L-galactose 1-phosphate</synonym>
    <synonym>L-Fucose 1-phosphate</synonym>
    <synonym>6-Deoxy-L-galactose 1-phosphoric acid</synonym>
    <synonym>L-Fucose 1-phosphoric acid</synonym>
    <synonym>Fucose 1-phosphoric acid</synonym>
    <synonym>(3,4,5-Trihydroxy-6-methyl-tetrahydropyran-2-yl)oxyphosphonate</synonym>
    <synonym>(3,4,5-Trihydroxy-6-methyl-tetrahydropyran-2-yl)oxyphosphonic acid</synonym>
    <synonym>6-Deoxy-L-galactopyranose 1-(dihydrogen phosphate)</synonym>
    <synonym>Fuculose 1-phosphate</synonym>
    <synonym>L-Fucose-1P</synonym>
  </synonyms>
  <chemical_formula>C6H13O8P</chemical_formula>
  <average_molecular_weight>244.1364</average_molecular_weight>
  <monisotopic_moleculate_weight>244.034803904</monisotopic_moleculate_weight>
  <iupac_name>{[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>fuculose 1-phosphate</traditional_iupac>
  <cas_registry_number>16562-58-6</cas_registry_number>
  <smiles>C[C@@H]1OC(OP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H13O8P/c1-2-3(7)4(8)5(9)6(13-2)14-15(10,11)12/h2-9H,1H3,(H2,10,11,12)/t2-,3+,4+,5-,6?/m0/s1</inchi>
  <inchikey>PTVXQARCLQPGIR-DHVFOXMCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharide phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</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>Alkyl phosphate</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>deoxyaldohexose phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.16</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)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>244.1364</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>244.034803904</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H]1OC(OP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O8P/c1-2-3(7)4(8)5(9)6(13-2)14-15(10,11)12/h2-9H,1H3,(H2,10,11,12)/t2-,3+,4+,5-,6?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PTVXQARCLQPGIR-DHVFOXMCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>136.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355803</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>388911</chemspider_id>
  <kegg_id>C02985</kegg_id>
  <pubchem_compound_id>439871</pubchem_compound_id>
  <foodb_id>FDB022520</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>28319</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>40955</bigg_id>
  <wikipedia_id/>
  <metlin_id>6120</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP02887</protein_accession>
      <name>Fucose-1-phosphate guanylyltransferase</name>
      <uniprot_id>E1B9U5</uniprot_id>
      <gene_name>FPGT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02888</protein_accession>
      <name>FUK protein</name>
      <uniprot_id>A6QP44</uniprot_id>
      <gene_name>FCSK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
