<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:11 UTC</creation_date>
  <update_date>2025-11-18 23:37:03 UTC</update_date>
  <accession>FDB012466</accession>
  <name>alpha-Eleostearic acid</name>
  <description>Isolated from seed oil of Momordica charantia (bitter melon). alpha-Eleostearic acid is found in bitter gourd and fruits.</description>
  <synonyms>
    <synonym>(9e,11Z,13e)-9,11,13-Octadecatrienoate</synonym>
    <synonym>(9E,11Z,13E)-9,11,13-octadecatrienoic acid</synonym>
    <synonym>(9E,11Z,13E)-octadeca-9,11,13-trienoic acid</synonym>
    <synonym>(9Z,11E,13E)-9,11,13-Octadecatrienoic acid</synonym>
    <synonym>(9Z,11E,13E)-Octadecatrienoic acid</synonym>
    <synonym>(e,Z,e)-9,11,13-Octadecatrienoate</synonym>
    <synonym>(E,Z,E)-9,11,13-octadecatrienoic acid</synonym>
    <synonym>(E,Z,E)-octadeca-9,11,13-trienoic acid</synonym>
    <synonym>9-trans,11-cis,13-trans-Octadecatrienoate</synonym>
    <synonym>9-trans,11-cis,13-trans-Octadecatrienoic acid</synonym>
    <synonym>9,11,13-Octadecatrienoic acid, (E,Z,E)-</synonym>
    <synonym>9t,11c,13t-CLN</synonym>
    <synonym>9t,11c,13t-CLnA</synonym>
    <synonym>9t,11c,13t-Conjugated linolenate</synonym>
    <synonym>9t,11c,13t-Conjugated linolenic acid</synonym>
    <synonym>9t,11c,13t-Linolenate</synonym>
    <synonym>9t,11c,13t-Linolenic acid</synonym>
    <synonym>9trans,11-cis,13trans-Octadecatrienoate</synonym>
    <synonym>9trans,11-cis,13trans-Octadecatrienoic acid</synonym>
    <synonym>a-Eleostearic acid</synonym>
    <synonym>alpha-Eleostearic acid</synonym>
    <synonym>C18:3 N-5 trans, 7 cis, 9 trans</synonym>
    <synonym>Elaeomargarinic acid</synonym>
    <synonym>Elaeostearinic acid</synonym>
    <synonym>Margarolic acid</synonym>
    <synonym>Octadeca-9t,11c,13t-trienoate</synonym>
    <synonym>Octadeca-9t,11c,13t-trienoic acid</synonym>
    <synonym>Octadeca-9t,11c,13t-triensaeure</synonym>
    <synonym>t9,c11,t13-CLN</synonym>
    <synonym>t9,c11,t13-CLnA</synonym>
    <synonym>t9,c11,t13-Conjugated linolenate</synonym>
    <synonym>t9,c11,t13-Conjugated linolenic acid</synonym>
    <synonym>t9,c11,t13-Linolenate</synonym>
    <synonym>t9,c11,t13-Linolenic acid</synonym>
  </synonyms>
  <chemical_formula>C18H30O2</chemical_formula>
  <average_molecular_weight>278.4296</average_molecular_weight>
  <monisotopic_moleculate_weight>278.224580204</monisotopic_moleculate_weight>
  <iupac_name>(9E,11Z,13E)-octadeca-9,11,13-trienoic acid</iupac_name>
  <traditional_iupac>9t,11c,13t-linolenic acid</traditional_iupac>
  <cas_registry_number>544-72-9</cas_registry_number>
  <smiles>CCCC\C=C\C=C/C=C/CCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5+,8-7-,10-9+</inchi>
  <inchikey>CUXYLFPMQMFGPL-MRZTUZPCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.</description>
    <direct_parent>Lineolic acids and derivatives</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Lineolic acids and derivatives</sub_class>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Octadecanoid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>9,11,13-octadecatrienoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.42e-04 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 49-49.2°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>6.06</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>4.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(9E,11Z,13E)-octadeca-9,11,13-trienoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>278.4296</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>278.224580204</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CCCC\C=C\C=C/C=C/CCCCCCCC(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C18H30O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5+,8-7-,10-9+</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>CUXYLFPMQMFGPL-MRZTUZPCSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>37.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>89.64</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>35.91</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>13</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>1</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>14992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>42274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>157887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>72420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>72421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>72422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>131346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>131347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>131348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2725883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2725884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2725885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2956815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2956816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2956817</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB30963</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>38383</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x00007f093c149690&gt;</reference>
    <reference>#&lt;Reference:0x00007f093c1494d8&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Bitter gourd</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Momordica charantia</name_scientific>
      <ncbi_taxonomy_id>3673</ncbi_taxonomy_id>
      <average_value>11815.1</average_value>
      <max_value>11815.1</max_value>
      <min_value>11815.1</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Fruits</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Anti feedant</name>
      <id>275</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Insecticide</name>
      <id>1040</id>
      <definition>Strictly, a substance intended to kill members of the class Insecta.  In common usage, any substance used for preventing, destroying, repelling or controlling insects.</definition>
    </health_effect>
    <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_effects>
</compound>
