<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:11:56 UTC</creation_date>
  <update_date>2019-11-26 03:11:53 UTC</update_date>
  <accession>FDB015577</accession>
  <name>Tormentic acid</name>
  <description>Tormentic acid, also known as tormentate, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Tormentic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Tormentic acid can be found in loquat and olive, which makes tormentic acid a potential biomarker for the consumption of these food products. Tormentic acid is a bio-active isolate of Luehea divaricata and Agrimonia eupatoria. Tormentic acid derivatives have been synthesized and researched .</description>
  <synonyms>
    <synonym>2,3,19-Trihydroxyurs-12-en-28-oic acid (2alpha,3beta)-</synonym>
    <synonym>Tomentic acid</synonym>
    <synonym>Tormentic acid</synonym>
    <synonym>Urs-12-en-28-oic acid, 2,3,19-trihydroxy-, (2alpha,3beta)-</synonym>
  </synonyms>
  <chemical_formula>C30H48O5</chemical_formula>
  <average_molecular_weight>488.6991</average_molecular_weight>
  <monisotopic_moleculate_weight>488.350174646</monisotopic_moleculate_weight>
  <iupac_name>(1R,2R,4aS,6aS,6bR,10R,11R,12aR,12bR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid</iupac_name>
  <traditional_iupac>(1R,2R,4aS,6aS,6bR,10R,11R,12aR,12bR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid</traditional_iupac>
  <cas_registry_number>13850-16-3</cas_registry_number>
  <smiles>CC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C)C5CCC34C)C2C1(C)O)C(O)=O</smiles>
  <inchi>InChI=1S/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)</inchi>
  <inchikey>OXVUXGFZHDKYLS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as taraxastane, ursane, and bauerane triterpenoids. These are triterpenoids with a structure based on either the taraxastane, ursane, or bauerane skeleton. These are obtained by methyl migration in ring E of the oleanane backbone.</description>
    <direct_parent>Taraxastane, ursane, and bauerane 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 name="" source="FooDB" kind=""/>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 273°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>4.27</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>4.64</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(1R,2R,4aS,6aS,6bR,10R,11R,12aR,12bR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>488.6991</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>488.350174646</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C)C5CCC34C)C2C1(C)O)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C30H48O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>OXVUXGFZHDKYLS-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>97.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>136.66</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>56.54</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>505804</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Loquat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Eriobotrya japonica</name_scientific>
      <ncbi_taxonomy_id>32224</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Olive</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Olea europaea</name_scientific>
      <ncbi_taxonomy_id>4146</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Hypoglycemic</name>
      <id>1017</id>
      <definition>A drug which lowers the blood glucose level.</definition>
    </health_effect>
  </health_effects>
</compound>
