<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 23:18:47 UTC</creation_date>
  <update_date>2020-04-22 15:16:24 UTC</update_date>
  <accession>BMDB0005806</accession>
  <secondary_accessions>
    <accession>BMDB05806</accession>
  </secondary_accessions>
  <name>Gamma-terpinene</name>
  <description/>
  <synonyms>
    <synonym>1,4-p-Menthadiene</synonym>
    <synonym>1-Isopropyl-4-methyl-1,4-cyclohexadiene</synonym>
    <synonym>1-Isopropyl-4-methylcyclohexa-1,4-diene</synonym>
    <synonym>1-Methyl-4-(1-methylethyl)-1,4-cyclohexadiene</synonym>
    <synonym>1-Methyl-4-propan-2-ylcyclohexa-1,4-diene</synonym>
    <synonym>4-Isopropyl-1-methyl-1,4-cyclohexadiene</synonym>
    <synonym>Crithmene</synonym>
    <synonym>Moslene</synonym>
    <synonym>p-Mentha-1,4-diene</synonym>
    <synonym>g-Terpinene</synonym>
    <synonym>Γ-terpinene</synonym>
    <synonym>1-Methyl-4-(propan-2-yl)cyclohexa-1,4-diene</synonym>
    <synonym>alpha Terpinene</synonym>
    <synonym>gamma Terpinene</synonym>
    <synonym>gamma-Terpinen</synonym>
    <synonym>Terpinene</synonym>
    <synonym>1-Methyl-4-isopropyl-1,4-cyclohexadiene</synonym>
    <synonym>gamma-Terpinene</synonym>
    <synonym>γ-Terpinen</synonym>
  </synonyms>
  <chemical_formula>C10H16</chemical_formula>
  <average_molecular_weight>136.238</average_molecular_weight>
  <monisotopic_moleculate_weight>136.125200515</monisotopic_moleculate_weight>
  <iupac_name>1-methyl-4-(propan-2-yl)cyclohexa-1,4-diene</iupac_name>
  <traditional_iupac>α terpinene</traditional_iupac>
  <cas_registry_number>99-85-4</cas_registry_number>
  <smiles>CC(C)C1=CCC(C)=CC1</smiles>
  <inchi>InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,7-8H,5-6H2,1-3H3</inchi>
  <inchikey>YKFLAYDHMOASIY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Hydrocarbons</super_class>
    <class>Unsaturated hydrocarbons</class>
    <sub_class>Branched unsaturated hydrocarbons</sub_class>
    <direct_parent>Branched unsaturated hydrocarbons</direct_parent>
    <alternative_parents>
      <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>Olefin</substituent>
      <substituent>Unsaturated aliphatic hydrocarbon</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Cyclic monoterpenes</external_descriptor>
      <external_descriptor>Menthane monoterpenoids</external_descriptor>
      <external_descriptor>Menthane monoterpenoids</external_descriptor>
      <external_descriptor>a monoterpenoid</external_descriptor>
      <external_descriptor>monoterpene</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-10 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.00868 mg/mL at 22 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.5</value>
      <source>LI,J &amp; PERDUE,EM (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-methyl-4-(propan-2-yl)cyclohexa-1,4-diene</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>136.238</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>136.125200515</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)C1=CCC(C)=CC1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,7-8H,5-6H2,1-3H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YKFLAYDHMOASIY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.61</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>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</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::NmrOneD</type>
      <spectrum_id>2747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>103757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>162006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1471132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1471133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2358006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2358007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2358008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2604479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2604480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2604481</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB015968</foodb_id>
  <chemspider_id>7181</chemspider_id>
  <knapsack_id>C00003061</knapsack_id>
  <pubchem_compound_id>7461</pubchem_compound_id>
  <kegg_id>C09900</kegg_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <chebi_id>10577</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>CPD-8736</meta_cyc_id>
  <wikipedia_id>Terpinene</wikipedia_id>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Richter, Friedrich; Wolff, Werner; Presting, W.  g-Terpinene. II.    Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen  (1930),  63B  1714-21.  CODEN: BDCBAD  ISSN:0365-9488.  CAN 24:46537  AN 1930:46537</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
