<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:13:03 UTC</creation_date>
  <update_date>2019-11-26 03:14:43 UTC</update_date>
  <accession>FDB017365</accession>
  <name>Bicyclogermacrene</name>
  <description>Constituent of the peel oil of Citrus junos (yuzu). Bicyclogermacrene is found in many foods, some of which are common oregano, lemon balm, hyssop, and orange mint.</description>
  <synonyms>
    <synonym>N(6)-(n-threonylcarbonyl)adenosine</synonym>
  </synonyms>
  <chemical_formula>C15H24</chemical_formula>
  <average_molecular_weight>204.3511</average_molecular_weight>
  <monisotopic_moleculate_weight>204.187800768</monisotopic_moleculate_weight>
  <iupac_name>(2Z,6Z)-3,7,11,11-tetramethylbicyclo[8.1.0]undeca-2,6-diene</iupac_name>
  <traditional_iupac>(2Z,6Z)-3,7,11,11-tetramethylbicyclo[8.1.0]undeca-2,6-diene</traditional_iupac>
  <cas_registry_number>24703-35-3</cas_registry_number>
  <smiles>C\C1=C\CC\C(C)=C/C2C(CC1)C2(C)C</smiles>
  <inchi>InChI=1S/C15H24/c1-11-6-5-7-12(2)10-14-13(9-8-11)15(14,3)4/h6,10,13-14H,5,7-9H2,1-4H3/b11-6-,12-10-</inchi>
  <inchikey>VPDZRSSKICPUEY-SUYBHAEQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as bicyclogermacrane and isolepidozane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the bicyclogermacrane (3,7,11,11-tetramethylbicyclo[8.1.0]undecane, 9CI) skeleton or the isolepidozane skeleton.</description>
    <direct_parent>Bicyclogermacrane and isolepidozane 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 homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Branched unsaturated hydrocarbons</alternative_parent>
      <alternative_parent>Cyclic olefins</alternative_parent>
      <alternative_parent>Polycyclic hydrocarbons</alternative_parent>
      <alternative_parent>Unsaturated aliphatic hydrocarbons</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Bicyclogermacrane sesquiterpenoid</substituent>
      <substituent>Branched unsaturated hydrocarbon</substituent>
      <substituent>Cyclic olefin</substituent>
      <substituent>Hydrocarbon</substituent>
      <substituent>Olefin</substituent>
      <substituent>Polycyclic hydrocarbon</substituent>
      <substituent>Unsaturated aliphatic hydrocarbon</substituent>
      <substituent>Unsaturated hydrocarbon</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.37e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>4.46</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2Z,6Z)-3,7,11,11-tetramethylbicyclo[8.1.0]undeca-2,6-diene</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>204.3511</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>204.187800768</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>C\C1=C\CC\C(C)=C/C2C(CC1)C2(C)C</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C15H24</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C15H24/c1-11-6-5-7-12(2)10-14-13(9-8-11)15(14,3)4/h6,10,13-14H,5,7-9H2,1-4H3/b11-6-,12-10-</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>VPDZRSSKICPUEY-SUYBHAEQSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>68.52</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>25.91</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>0</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>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>131991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>139725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>103491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>103492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>103493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>169545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>169546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>169547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2284543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2284544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2284545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3081783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3081784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3081785</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB38137</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce3192f608&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Citrus</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Common oregano</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Origanum vulgare</name_scientific>
      <ncbi_taxonomy_id>39352</ncbi_taxonomy_id>
      <average_value>19.55</average_value>
      <max_value>19.55</max_value>
      <min_value>19.55</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Coriander</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Coriandrum sativum</name_scientific>
      <ncbi_taxonomy_id>4047</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Hyssop</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Hyssopus officinalis</name_scientific>
      <ncbi_taxonomy_id>39324</ncbi_taxonomy_id>
      <average_value>76.4</average_value>
      <max_value>76.4</max_value>
      <min_value>76.4</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Lemon balm</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Melissa officinalis</name_scientific>
      <ncbi_taxonomy_id>39338</ncbi_taxonomy_id>
      <average_value>0.45</average_value>
      <max_value>0.45</max_value>
      <min_value>0.45</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Orange mint</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mentha aquatica</name_scientific>
      <ncbi_taxonomy_id>190902</ncbi_taxonomy_id>
      <average_value>0.45</average_value>
      <max_value>0.45</max_value>
      <min_value>0.45</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Parsley</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Petroselinum crispum</name_scientific>
      <ncbi_taxonomy_id>4043</ncbi_taxonomy_id>
      <average_value>0.516</average_value>
      <max_value>0.516</max_value>
      <min_value>0.516</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Sweet bay</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Laurus nobilis</name_scientific>
      <ncbi_taxonomy_id>85223</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sweet marjoram</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Origanum majorana</name_scientific>
      <ncbi_taxonomy_id>268884</ncbi_taxonomy_id>
      <average_value>4.05</average_value>
      <max_value>4.05</max_value>
      <min_value>4.05</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>green</name>
    </flavor>
    <flavor>
      <name>wood</name>
    </flavor>
    <flavor>
      <name>woody</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
