<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 23:05:00 UTC</creation_date>
  <update_date>2020-05-21 16:29:05 UTC</update_date>
  <accession>BMDB0003514</accession>
  <secondary_accessions>
    <accession>BMDB03514</accession>
  </secondary_accessions>
  <name>Alpha-D-Glucose 1,6-bisphosphate</name>
  <description>Alpha-D-Alpha-d-alpha-d-glucose 1,6-bisphosphate, also known as α-Alphalpha-d-alpha-d-glucose 1,6-bisphosphate or alpha-d-glucose 1,6-bisphosphate, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Alpha-D-Alpha-d-alpha-d-glucose 1,6-bisphosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Alpha-D-Alpha-d-alpha-d-glucose 1,6-bisphosphate exists in all living species, ranging from bacteria to humans. Alpha-D-Alpha-d-alpha-d-glucose 1,6-bisphosphate and 3-phosphoglyceric acid can be biosynthesized from glucose 1-phosphate and glyceric acid 1,3-biphosphate through the action of the enzyme alpha-d-glucose 1,6-bisphosphate synthase. In cattle, Alpha-Alpha-alphalpha-d-alpha-d-glucose 1,6-bisphosphate is involved in the metabolic pathway called the starch and sucrose metabolism pathway.</description>
  <synonyms>
    <synonym>alpha-D-Glucose 1,6-biphosphate</synonym>
    <synonym>D-Glucose 1,6-biphosphate</synonym>
    <synonym>D-Glucose 1,6-bisphosphate</synonym>
    <synonym>a-D-Glucose 1,6-biphosphate</synonym>
    <synonym>a-D-Glucose 1,6-biphosphoric acid</synonym>
    <synonym>alpha-D-Glucose 1,6-biphosphoric acid</synonym>
    <synonym>Α-D-glucose 1,6-biphosphate</synonym>
    <synonym>Α-D-glucose 1,6-biphosphoric acid</synonym>
    <synonym>D-Glucose 1,6-biphosphoric acid</synonym>
    <synonym>D-Glucose 1,6-bisphosphoric acid</synonym>
    <synonym>a-D-Glucose 1,6-bisphosphate</synonym>
    <synonym>a-D-Glucose 1,6-bisphosphoric acid</synonym>
    <synonym>alpha-D-Glucose 1,6-bisphosphoric acid</synonym>
    <synonym>Α-D-glucose 1,6-bisphosphate</synonym>
    <synonym>Α-D-glucose 1,6-bisphosphoric acid</synonym>
    <synonym>a-D-Glucose 1,6-bis(dihydrogen phosphate)</synonym>
    <synonym>a-D-Glucose 1,6-diphosphate</synonym>
    <synonym>alpha-D-1,6-Bis(dihydrogen phosphate) glucopyranose</synonym>
    <synonym>alpha-D-Glucose 1,6-bis(dihydrogen phosphate)</synonym>
    <synonym>alpha-D-Glucose 1,6-diphosphate</synonym>
    <synonym>alpha-delta-1,6-Bis(dihydrogen phosphate) glucopyranose</synonym>
    <synonym>alpha-delta-Glucose 1,6-bis(dihydrogen phosphate)</synonym>
    <synonym>alpha-delta-Glucose 1,6-bisphosphate</synonym>
    <synonym>alpha-delta-Glucose 1,6-diphosphate</synonym>
    <synonym>D-Glucose 1,6-diphosphate</synonym>
    <synonym>delta-Glucose 1,6-diphosphate</synonym>
    <synonym>Glucose 1,6-bisphosphate</synonym>
    <synonym>Glucose 1,6-diphosphate</synonym>
    <synonym>beta-D-Glucose 1,6-(bis)phosphate</synonym>
    <synonym>Glucose-1,6-diphosphate</synonym>
    <synonym>Glucose-1,6-bisphosphate</synonym>
    <synonym>alpha-Glucose 1,6-diphosphate</synonym>
    <synonym>Α-D-glucose 1,6-diphosphate</synonym>
    <synonym>Α-glucose 1,6-diphosphate</synonym>
    <synonym>alpha-D-Glucose 1,6-bisphosphate</synonym>
  </synonyms>
  <chemical_formula>C6H14O12P2</chemical_formula>
  <average_molecular_weight>340.1157</average_molecular_weight>
  <monisotopic_moleculate_weight>339.996048936</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>10139-18-1</cas_registry_number>
  <smiles>O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H](OP(O)(O)=O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H14O12P2/c7-3-2(1-16-19(10,11)12)17-6(5(9)4(3)8)18-20(13,14)15/h2-9H,1H2,(H2,10,11,12)(H2,13,14,15)/t2-,3-,4+,5-,6-/m1/s1</inchi>
  <inchikey>RWHOZGRAXYWRNX-VFUOTHLCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.</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>Hexose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</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>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hexose phosphate</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>D-glucose 1,6-bisphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>logp</kind>
      <value>-4.374</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>340.1157</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>339.996048936</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H](OP(O)(O)=O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H14O12P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H14O12P2/c7-3-2(1-16-19(10,11)12)17-6(5(9)4(3)8)18-20(13,14)15/h2-9H,1H2,(H2,10,11,12)(H2,13,14,15)/t2-,3-,4+,5-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RWHOZGRAXYWRNX-VFUOTHLCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>203.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>57.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</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>0</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>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>134252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>141986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28101</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Placenta</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01231</kegg_id>
  <foodb_id>FDB023185</foodb_id>
  <chemspider_id>74362</chemspider_id>
  <pubchem_compound_id>82400</pubchem_compound_id>
  <drugbank_id>DB02835</drugbank_id>
  <chebi_id>18148</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id>ALPHA-GLUCOSE-16-BISPHOSPHATE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP02984</protein_accession>
      <name>PGM2L1 protein</name>
      <uniprot_id>A5PKH8</uniprot_id>
      <gene_name>PGM2L1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
