<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:59 UTC</creation_date>
  <update_date>2025-11-18 22:54:10 UTC</update_date>
  <accession>FDB003856</accession>
  <name>Germacrene D</name>
  <description>Germacrene d, also known as germacrene d, (s-(e,e))-isomer, is a member of the class of compounds known as germacrane sesquiterpenoids. Germacrane sesquiterpenoids are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Germacrene d can be found in a number of food items such as peppermint, roman camomile, hyssop, and common walnut, which makes germacrene d a potential biomarker for the consumption of these food products. </description>
  <synonyms>
    <synonym>(+)-germacrene d</synonym>
    <synonym>(1E,5E,7betaH)-germacra-1(10),4(15),5-triene</synonym>
    <synonym>(1E,5E,7xi)-germacra-1(10),4(15),5-triene</synonym>
    <synonym>1-Methyl-5-methylene-7-(1-methylethyl)-1,6-cyclodecadiene</synonym>
    <synonym>1,6-Cyclodecadiene, 1-methyl-5-methylene-7-(1-methylethyl)-</synonym>
    <synonym>1(10),4(14),5-Germacratriene</synonym>
    <synonym>8-Isopropyl-1-methyl-5-methylene-1,6-cyclodecadiene</synonym>
    <synonym>D-germacrene</synonym>
    <synonym>Germacren d</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>(1E,6E,8S)-1-methyl-5-methylidene-8-(propan-2-yl)cyclodeca-1,6-diene</iupac_name>
  <traditional_iupac>(-)-germacrene D</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(C)[C@@H]1CC\C(C)=C\CCC(=C)\C=C\1</smiles>
  <inchi>InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h7-8,10,12,15H,3,5-6,9,11H2,1-2,4H3/b10-8+,14-7+/t15-/m0/s1</inchi>
  <inchikey>GAIBLDCXCZKKJE-RXJOXMPGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups.</description>
    <direct_parent>Germacrane 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 homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Branched unsaturated hydrocarbons</alternative_parent>
      <alternative_parent>Cyclic olefins</alternative_parent>
      <alternative_parent>Unsaturated aliphatic hydrocarbons</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Branched unsaturated hydrocarbon</substituent>
      <substituent>Cyclic olefin</substituent>
      <substituent>Germacrane sesquiterpenoid</substituent>
      <substituent>Hydrocarbon</substituent>
      <substituent>Olefin</substituent>
      <substituent>Unsaturated aliphatic hydrocarbon</substituent>
      <substituent>Unsaturated hydrocarbon</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>germacrene D</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.16e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>4.92</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(1E,6E,8S)-1-methyl-5-methylidene-8-(propan-2-yl)cyclodeca-1,6-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>CC(C)[C@@H]1CC\C(C)=C\CCC(=C)\C=C\1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C15H24</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h7-8,10,12,15H,3,5-6,9,11H2,1-2,4H3/b10-8+,14-7+/t15-/m0/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>GAIBLDCXCZKKJE-RXJOXMPGSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>70.55</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>25.86</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</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::EiMs</type>
      <spectrum_id>3114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3599533</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Caraway</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Carum carvi</name_scientific>
      <ncbi_taxonomy_id>48032</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>66.6</average_value>
      <max_value>66.6</max_value>
      <min_value>66.6</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Common walnut</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Juglans regia</name_scientific>
      <ncbi_taxonomy_id>51240</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cornmint</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mentha arvensis</name_scientific>
      <ncbi_taxonomy_id>292239</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Dill</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anethum graveolens</name_scientific>
      <ncbi_taxonomy_id>40922</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Fig</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ficus carica</name_scientific>
      <ncbi_taxonomy_id>3494</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Ginger</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zingiber officinale</name_scientific>
      <ncbi_taxonomy_id>94328</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>92.233333</average_value>
      <max_value>155.2</max_value>
      <min_value>10.5</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>54.2</average_value>
      <max_value>54.2</max_value>
      <min_value>54.2</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Nutmeg</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Myristica fragrans</name_scientific>
      <ncbi_taxonomy_id>51089</ncbi_taxonomy_id>
    </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>7.75</average_value>
      <max_value>7.75</max_value>
      <min_value>7.75</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Papaya</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Carica papaya</name_scientific>
      <ncbi_taxonomy_id>3649</ncbi_taxonomy_id>
    </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>0.69</average_value>
      <max_value>0.69</max_value>
      <min_value>0.69</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Pepper (Spice)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Piper nigrum</name_scientific>
      <ncbi_taxonomy_id>13216</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Peppermint</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mentha X piperita</name_scientific>
      <ncbi_taxonomy_id>34256</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Roman camomile</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Chamaemelum nobile</name_scientific>
      <ncbi_taxonomy_id>99037</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Safflower</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Carthamus tinctorius</name_scientific>
      <ncbi_taxonomy_id>4222</ncbi_taxonomy_id>
      <average_value>0.004</average_value>
      <max_value>0.004</max_value>
      <min_value>0.004</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Spearmint</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mentha spicata</name_scientific>
      <ncbi_taxonomy_id>29719</ncbi_taxonomy_id>
      <average_value>449.5</average_value>
      <max_value>449.5</max_value>
      <min_value>449.5</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Sweet basil</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ocimum basilicum</name_scientific>
      <ncbi_taxonomy_id>39350</ncbi_taxonomy_id>
      <average_value>3.5</average_value>
      <max_value>3.5</max_value>
      <min_value>3.5</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Winter savory</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Satureja montana</name_scientific>
      <ncbi_taxonomy_id>49988</ncbi_taxonomy_id>
      <average_value>5.0</average_value>
      <max_value>5.0</max_value>
      <min_value>5.0</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Pesticide</name>
      <id>1210</id>
      <definition>Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.</definition>
    </health_effect>
    <health_effect>
      <name>Pheromone</name>
      <id>1214</id>
      <definition>A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.</definition>
    </health_effect>
  </health_effects>
</compound>
