<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:29 UTC</creation_date>
  <update_date>2019-11-26 03:07:52 UTC</update_date>
  <accession>FDB013016</accession>
  <name>Glabrolide</name>
  <description>Constituent of Glycyrrhiza glabra (licorice) and Glycyrrhiza uralensis (Chinese licorice). Glabrolide is found in herbs and spices.</description>
  <synonyms>
    <synonym>3b-Hydroxy-11-oxo-12-oleanen-30,22b-olide</synonym>
    <synonym>Glabrolide</synonym>
  </synonyms>
  <chemical_formula>C30H44O4</chemical_formula>
  <average_molecular_weight>468.668</average_molecular_weight>
  <monisotopic_moleculate_weight>468.323959896</monisotopic_moleculate_weight>
  <iupac_name>11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-16,22-dione</iupac_name>
  <traditional_iupac>11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-16,22-dione</traditional_iupac>
  <cas_registry_number>10401-33-9</cas_registry_number>
  <smiles>CC12CC(OC1=O)C1(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC34C)C1C2</smiles>
  <inchi>InChI=1S/C30H44O4/c1-25(2)20-8-11-30(7)23(28(20,5)10-9-21(25)32)19(31)14-17-18-15-26(3)16-22(34-24(26)33)27(18,4)12-13-29(17,30)6/h14,18,20-23,32H,8-13,15-16H2,1-7H3</inchi>
  <inchikey>SSHDNSCEQSPWIM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.</description>
    <direct_parent>Triterpenoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Triterpenoids</sub_class>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Gamma butyrolactones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxepanes</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Caprolactone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Gamma butyrolactone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Lactone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxepane</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.73e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 360-365°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>5.46</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>17.79</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-0.84</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-16,22-dione</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>468.668</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>468.323959896</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC12CC(OC1=O)C1(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC34C)C1C2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C30H44O4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C30H44O4/c1-25(2)20-8-11-30(7)23(28(20,5)10-9-21(25)32)19(31)14-17-18-15-26(3)16-22(34-24(26)33)27(18,4)12-13-29(17,30)6/h14,18,20-23,32H,8-13,15-16H2,1-7H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>SSHDNSCEQSPWIM-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>63.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>132.29</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>54.13</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</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::CMs</type>
      <spectrum_id>22756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>43904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>130706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>138440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2692433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2692434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2692435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2990360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2990361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2990362</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB34515</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce32311cc0&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Herbs and Spices</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
