<?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>2025-11-19 00:56:21 UTC</update_date>
  <accession>FDB015576</accession>
  <name>Euscaphic acid</name>
  <description>Constituent of Coleus amboinicus (Cuban oregano). Euscaphic acid is found in loquat and herbs and spices.</description>
  <synonyms>
    <synonym>Acuminatic acid</synonym>
    <synonym>Euscaphic acid</synonym>
    <synonym>Jacarandic acid</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,8aR,10S,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,8aR,10S,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>53155-25-2</cas_registry_number>
  <smiles>[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@](C)(O)[C@H](C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)C[C@@H](O)[C@@H](O)C2(C)C</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)/t17-,19-,20+,21-,22-,23-,26+,27-,28-,29-,30+/m1/s1</inchi>
  <inchikey>OXVUXGFZHDKYLS-QUFHAEKXSA-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 homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Dammarenes</external_descriptor>
      <external_descriptor>Ursanes</external_descriptor>
      <external_descriptor>hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>pentacyclic triterpenoid</external_descriptor>
      <external_descriptor>triol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.13e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 270-271° (264°)</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,8aR,10S,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>[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@](C)(O)[C@H](C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)C[C@@H](O)[C@@H](O)C2(C)C</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)/t17-,19-,20+,21-,22-,23-,26+,27-,28-,29-,30+/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>OXVUXGFZHDKYLS-QUFHAEKXSA-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>56.47</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>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>44954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>148128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2731854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2731855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2731856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2977634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2977635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2977636</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB36651</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:0x000055ce3258aa88&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>
    <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>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
