<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-10-03 18:34:36 UTC</creation_date>
  <update_date>2020-04-22 15:49:11 UTC</update_date>
  <accession>BMDB0012231</accession>
  <secondary_accessions>
    <accession>BMDB12231</accession>
  </secondary_accessions>
  <name>Geranylfarnesyl diphosphate</name>
  <description/>
  <synonyms>
    <synonym>(2E,6E,10E,14E)-Geranylfarnesyl diphosphate</synonym>
    <synonym>2-trans,6-trans,10-trans,14-trans-Geranylfarnesyl diphosphate</synonym>
    <synonym>all-trans-Farnesylgeranyl diphosphate</synonym>
    <synonym>all-trans-Farnesylgeranyl pyrophosphate</synonym>
    <synonym>all-trans-Geranylfarnesyl diphosphate</synonym>
    <synonym>all-trans-Geranylfarnesyl pyrophosphate</synonym>
    <synonym>(2E,6E,10E,14E)-Geranylfarnesyl diphosphoric acid</synonym>
    <synonym>2-trans,6-trans,10-trans,14-trans-Geranylfarnesyl diphosphoric acid</synonym>
    <synonym>all-trans-Farnesylgeranyl diphosphoric acid</synonym>
    <synonym>all-trans-Farnesylgeranyl pyrophosphoric acid</synonym>
    <synonym>all-trans-Geranylfarnesyl diphosphoric acid</synonym>
    <synonym>all-trans-Geranylfarnesyl pyrophosphoric acid</synonym>
    <synonym>Geranylfarnesyl diphosphoric acid</synonym>
    <synonym>all-trans-Pentaprenyl diphosphate</synonym>
    <synonym>Geranylfarnesyl-diphosphate</synonym>
    <synonym>Geranylfarnesyl-PP</synonym>
    <synonym>GFPP</synonym>
    <synonym>Geranylfarnesyl diphosphate</synonym>
    <synonym>all-trans-Pentaprenyl diphosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C25H44O7P2</chemical_formula>
  <average_molecular_weight>518.5602</average_molecular_weight>
  <monisotopic_moleculate_weight>518.256226786</monisotopic_moleculate_weight>
  <iupac_name>{[hydroxy({[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>geranylfarnesyl diphosphate</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C25H44O7P2/c1-21(2)11-7-12-22(3)13-8-14-23(4)15-9-16-24(5)17-10-18-25(6)19-20-31-34(29,30)32-33(26,27)28/h11,13,15,17,19H,7-10,12,14,16,18,20H2,1-6H3,(H,29,30)(H2,26,27,28)/b22-13+,23-15+,24-17+,25-19+</inchi>
  <inchikey>JMVSBFJBMXQNJW-GIXZANJISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as polyprenyl diphosphates. These are prenol lipids in which the diphosphate group is linked to one end of the polyprenol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Polyprenols</sub_class>
    <direct_parent>Polyprenyl diphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Isoprenoid phosphates</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Polyprenyl monophosphates</alternative_parent>
      <alternative_parent>Sesterterpenoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isoprenoid phosphate</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyprenyl diphosphate</substituent>
      <substituent>Polyprenyl monophosphate</substituent>
      <substituent>Sesterterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Acyclic sesterterpenoids</external_descriptor>
      <external_descriptor>Acyclic sesterterpenoids</external_descriptor>
      <external_descriptor>Polyterpenoids</external_descriptor>
      <external_descriptor>pentaprenyl diphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[hydroxy({[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>518.5602</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>518.256226786</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H44O7P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C25H44O7P2/c1-21(2)11-7-12-22(3)13-8-14-23(4)15-9-16-24(5)17-10-18-25(6)19-20-31-34(29,30)32-33(26,27)28/h11,13,15,17,19H,7-10,12,14,16,18,20H2,1-6H3,(H,29,30)(H2,26,27,28)/b22-13+,23-15+,24-17+,25-19+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JMVSBFJBMXQNJW-GIXZANJISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>144.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>57.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</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>0</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>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2364307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2364308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2364309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2602163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2602164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2602165</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB028874</foodb_id>
  <drugbank_id/>
  <chemspider_id>4444258</chemspider_id>
  <kegg_id>C04217</kegg_id>
  <chebi_id>16818</chebi_id>
  <pubchem_compound_id>5280659</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>ALL-TRANS-PENTAPRENYL-DIPHOSPHATE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Geranylfarnesyl pyrophosphate</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
