<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:07:24 UTC</creation_date>
  <update_date>2025-11-18 23:03:20 UTC</update_date>
  <accession>FDB006999</accession>
  <name>Manool</name>
  <description>Manool, also known as (+)-manool, is a member of the class of compounds known as diterpenoids. Diterpenoids are terpene compounds formed by four isoprene units. Manool is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Manool can be found in common sage, which makes manool a potential biomarker for the consumption of this food product. </description>
  <synonyms>
    <synonym>2-Ketoepimanool</synonym>
    <synonym>Labda-8(20),14-dien-13-ol, (13R)-</synonym>
    <synonym>Labda-8(20),14-dien-13-ol, (13R)- (8CI)</synonym>
    <synonym>Labda-8(20),14-dien-13-ol, (13S)-</synonym>
    <synonym>Manool</synonym>
  </synonyms>
  <chemical_formula>C20H34O</chemical_formula>
  <average_molecular_weight>290.4834</average_molecular_weight>
  <monisotopic_moleculate_weight>290.26096571</monisotopic_moleculate_weight>
  <iupac_name>5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]-3-methylpent-1-en-3-ol</iupac_name>
  <traditional_iupac>5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]-3-methylpent-1-en-3-ol</traditional_iupac>
  <cas_registry_number>596-85-0</cas_registry_number>
  <smiles>CC(O)(CC[C@H]1C(=C)CC[C@H]2C(C)(C)CCC[C@]12C)C=C</smiles>
  <inchi>InChI=1S/C20H34O/c1-7-19(5,21)14-11-16-15(2)9-10-17-18(3,4)12-8-13-20(16,17)6/h7,16-17,21H,1-2,8-14H2,3-6H3/t16-,17-,19?,20+/m0/s1</inchi>
  <inchikey>CECREIRZLPLYDM-OQLBXJDTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.</description>
    <direct_parent>Diterpenoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Diterpenoids</sub_class>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Diterpenoid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Labdane diterpenoid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.37e-04 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>5.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>18.33</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-1.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]-3-methylpent-1-en-3-ol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>290.4834</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>290.26096571</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(O)(CC[C@H]1C(=C)CC[C@H]2C(C)(C)CCC[C@]12C)C=C</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C20H34O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C20H34O/c1-7-19(5,21)14-11-16-15(2)9-10-17-18(3,4)12-8-13-20(16,17)6/h7,16-17,21H,1-2,8-14H2,3-6H3/t16-,17-,19?,20+/m0/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>CECREIRZLPLYDM-OQLBXJDTSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>20.23</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>91.08</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>36.33</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>1</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>96762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>96763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>96764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>161334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>161335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>161336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603532</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>Common sage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Salvia officinalis</name_scientific>
      <ncbi_taxonomy_id>38868</ncbi_taxonomy_id>
    </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>Termitifuge</name>
      <id>1350</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_effects>
</compound>
