<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:13:20 UTC</creation_date>
  <update_date>2015-07-21 06:57:11 UTC</update_date>
  <accession>FDB022394</accession>
  <name>Dolichyl beta-D-glucosyl phosphate</name>
  <description>Dolichyl &amp;#946;-D-glucosyl phosphate is a polyisoprenyl phosphate monosaccharide. Biosynthesis is by Glucosyltransferase in liver mitochondria. (PubMed ID 6450044 ) [HMDB]</description>
  <synonyms>
    <synonym>Dolichol monoate glucose</synonym>
    <synonym>Dolichol monophosphate glucose</synonym>
    <synonym>Dolichyl ate glucose</synonym>
    <synonym>Dolichyl b-D-glucosyl ate</synonym>
    <synonym>Dolichyl b-D-glucosyl phosphate</synonym>
    <synonym>Dolichyl b-D-glucosyl phosphic acid</synonym>
    <synonym>Dolichyl b-delta-glucosyl ate</synonym>
    <synonym>Dolichyl b-delta-glucosyl phosphate</synonym>
    <synonym>Dolichyl b-delta-glucosyl phosphic acid</synonym>
    <synonym>Dolichyl beta-D-glucosyl ate</synonym>
    <synonym>dolichyl beta-D-glucosyl phosphate</synonym>
    <synonym>Dolichyl beta-delta-glucosyl ate</synonym>
    <synonym>dolichyl beta-delta-glucosyl phosphate</synonym>
    <synonym>Dolichyl monoate glucose</synonym>
    <synonym>Dolichyl monophosphate glucose</synonym>
    <synonym>Dolichyl phosphate glucose</synonym>
    <synonym>Dolichyloryl glucose</synonym>
    <synonym>Dolichylphosphoryl glucose</synonym>
  </synonyms>
  <chemical_formula>C21H39O9P</chemical_formula>
  <average_molecular_weight>466.5027</average_molecular_weight>
  <monisotopic_moleculate_weight>466.233169358</monisotopic_moleculate_weight>
  <iupac_name>{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}[(3,7,11-trimethyldodeca-6,10-dien-1-yl)oxy]phosphinic acid</iupac_name>
  <traditional_iupac>[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy((3,7,11-trimethyldodeca-6,10-dien-1-yl)oxy)phosphinic acid</traditional_iupac>
  <cas_registry_number>220496-27-5</cas_registry_number>
  <smiles>[H][C@]1(CO)O[C@@]([H])(OP(O)(=O)OCCC(C)CCC=C(C)CCC=C(C)C)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O</smiles>
  <inchi>InChI=1S/C21H39O9P/c1-14(2)7-5-8-15(3)9-6-10-16(4)11-12-28-31(26,27)30-21-20(25)19(24)18(23)17(13-22)29-21/h7,9,16-25H,5-6,8,10-13H2,1-4H3,(H,26,27)/t16?,17-,18-,19+,20-,21+/m1/s1</inchi>
  <inchikey>RHJMCOLWMXJOGE-OKNYXOPQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.</description>
    <direct_parent>Sesquiterpenoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Sesquiterpenoids</sub_class>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Dialkyl phosphates</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharide 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>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Dialkyl phosphate</substituent>
      <substituent>Farsesane sesquiterpenoid</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sesquiterpenoid</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.18e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.25</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>1.62</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}[(3,7,11-trimethyldodeca-6,10-dien-1-yl)oxy]phosphinic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>466.5027</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>466.233169358</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>[H][C@]1(CO)O[C@@]([H])(OP(O)(=O)OCCC(C)CCC=C(C)CCC=C(C)C)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C21H39O9P</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C21H39O9P/c1-14(2)7-5-8-15(3)9-6-10-16(4)11-12-28-31(26,27)30-21-20(25)19(24)18(23)17(13-22)29-21/h7,9,16-25H,5-6,8,10-13H2,1-4H3,(H,26,27)/t16?,17-,18-,19+,20-,21+/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>RHJMCOLWMXJOGE-OKNYXOPQSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>145.91</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>117.31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>49.83</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>13</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>-1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1085257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181691</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB01054</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>15812</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce2d048570&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Dol-P-Glc:Glc(2)Man(9)GlcNAc(2)-PP-Dol alpha-1,2-glucosyltransferase</name>
      <uniprot_id>Q5BKT4</uniprot_id>
      <uniprot_name/>
      <gene_name>ALG10</gene_name>
    </enzyme>
    <enzyme>
      <name>Dolichyl pyrophosphate Man9GlcNAc2 alpha-1,3-glucosyltransferase</name>
      <uniprot_id>Q9Y672</uniprot_id>
      <uniprot_name/>
      <gene_name>ALG6</gene_name>
    </enzyme>
    <enzyme>
      <name>Dolichyl-phosphate beta-glucosyltransferase</name>
      <uniprot_id>Q9Y673</uniprot_id>
      <uniprot_name/>
      <gene_name>ALG5</gene_name>
    </enzyme>
    <enzyme>
      <name>Probable dolichyl pyrophosphate Glc1Man9GlcNAc2 alpha-1,3-glucosyltransferase</name>
      <uniprot_id>Q9BVK2</uniprot_id>
      <uniprot_name/>
      <gene_name>ALG8</gene_name>
    </enzyme>
    <enzyme>
      <name>Putative Dol-P-Glc:Glc(2)Man(9)GlcNAc(2)-PP-Dol alpha-1,2-glucosyltransferase</name>
      <uniprot_id>Q5I7T1</uniprot_id>
      <uniprot_name/>
      <gene_name>ALG10B</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
