<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:07:13 UTC</creation_date>
  <update_date>2025-11-18 23:02:23 UTC</update_date>
  <accession>FDB006615</accession>
  <name>beta-Pinone</name>
  <description>Beta-pinone, also known as B-pinone, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Beta-pinone is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Beta-pinone can be found in pepper (spice), which makes beta-pinone a potential biomarker for the consumption of this food product.</description>
  <synonyms>
    <synonym>(1R)-(+)-Norinone</synonym>
    <synonym>(1R)-6,6-DIMETHYLDICYCLO[3.1.1]HEPTAN-2-ONE</synonym>
    <synonym>&amp;beta;-pinone</synonym>
    <synonym>2-Norpinanone, 6,6-dimethyl-</synonym>
    <synonym>2-Norpinanone, 6,6-dimethyl- (8CI)</synonym>
    <synonym>6,6-Dimethylbicyclo(3.1.1)heptan-2-one</synonym>
    <synonym>6,6-Dimethylbicyclo[3.1.1]heptan-2-one</synonym>
    <synonym>Bicyclo(3.1.1)heptan-2-one, 6,6-dimethyl-</synonym>
    <synonym>Bicyclo(3.1.1)heptan-2-one, 6,6-dimethyl-, (1R)-</synonym>
    <synonym>Bicyclo[3.1.1]heptan-2-one, 6,6-dimethyl-</synonym>
    <synonym>Bicyclo[3.1.1]heptan-2-one, 6,6-dimethyl-, (1R)-</synonym>
    <synonym>Nopinon</synonym>
    <synonym>Nopinone</synonym>
  </synonyms>
  <chemical_formula>C9H14O</chemical_formula>
  <average_molecular_weight>138.2069</average_molecular_weight>
  <monisotopic_moleculate_weight>138.10446507</monisotopic_moleculate_weight>
  <iupac_name>6,6-dimethylbicyclo[3.1.1]heptan-2-one</iupac_name>
  <traditional_iupac>nopinone</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC1(C)C2CC1C(=O)CC2</smiles>
  <inchi>InChI=1S/C9H14O/c1-9(2)6-3-4-8(10)7(9)5-6/h6-7H,3-5H2,1-2H3</inchi>
  <inchikey>XZFDKWMYCUEKSS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.</description>
    <direct_parent>Bicyclic monoterpenoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Monoterpenoids</sub_class>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Bicyclic monoterpenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.23e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-7.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>6,6-dimethylbicyclo[3.1.1]heptan-2-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>138.2069</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>138.10446507</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1(C)C2CC1C(=O)CC2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C9H14O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C9H14O/c1-9(2)6-3-4-8(10)7(9)5-6/h6-7H,3-5H2,1-2H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>XZFDKWMYCUEKSS-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>17.07</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>39.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>16.01</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>1</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::MsMs</type>
      <spectrum_id>105870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105871</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>172485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>172486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>172487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603169</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>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>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
