<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:13 UTC</creation_date>
  <update_date>2025-11-18 23:37:37 UTC</update_date>
  <accession>FDB012532</accession>
  <name>Levistolide A</name>
  <description>Constituent of Levisticum officinale (lovage). Levistolide A is found in lovage and herbs and spices.</description>
  <synonyms>
    <synonym>Isodiospyrin</synonym>
    <synonym>Isoldiospyrin</synonym>
    <synonym>Levistolide A</synonym>
  </synonyms>
  <chemical_formula>C24H28O4</chemical_formula>
  <average_molecular_weight>380.4767</average_molecular_weight>
  <monisotopic_moleculate_weight>380.198759384</monisotopic_moleculate_weight>
  <iupac_name>(6Z,16Z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione</iupac_name>
  <traditional_iupac>(6Z,16Z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione</traditional_iupac>
  <cas_registry_number>89708-23-6</cas_registry_number>
  <smiles>CCC\C=C1/OC(=O)C2=C1CCC1C3CCC4(C21)\C(OC(=O)C4=C3)=C\CCC</smiles>
  <inchi>InChI=1S/C24H28O4/c1-3-5-7-18-16-10-9-15-14-11-12-24(21(15)20(16)23(26)27-18)17(13-14)22(25)28-19(24)8-6-4-2/h7-8,13-15,21H,3-6,9-12H2,1-2H3/b18-7-,19-8-</inchi>
  <inchikey>UBBRXVRQZJSDAK-DZWUWFSDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.</description>
    <direct_parent>Butenolides</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Dihydrofurans</class>
    <sub_class>Furanones</sub_class>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Enoate esters</alternative_parent>
      <alternative_parent>Enol esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-furanone</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Alpha,beta-unsaturated carboxylic ester</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Enoate ester</substituent>
      <substituent>Enol ester</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.58e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 112-113°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>4.69</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-6.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(6Z,16Z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>380.4767</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>380.198759384</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CCC\C=C1/OC(=O)C2=C1CCC1C3CCC4(C21)\C(OC(=O)C4=C3)=C\CCC</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C24H28O4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C24H28O4/c1-3-5-7-18-16-10-9-15-14-11-12-24(21(15)20(16)23(26)27-18)17(13-14)22(25)28-19(24)8-6-4-2/h7-8,13-15,21H,3-6,9-12H2,1-2H3/b18-7-,19-8-</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>UBBRXVRQZJSDAK-DZWUWFSDSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>52.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>110.23</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>42.13</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>2</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>24376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>166217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2703389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2703390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2703391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3002743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3002744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3002745</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB0034225</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>Herbs and Spices</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Lovage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Levisticum officinale</name_scientific>
      <ncbi_taxonomy_id>48042</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
