<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2018-06-25 21:54:26 UTC</creation_date>
  <update_date>2020-06-04 20:59:24 UTC</update_date>
  <accession>BMDB0062151</accession>
  <secondary_accessions>
    <accession>BMDB62151</accession>
  </secondary_accessions>
  <name>10E, 12E-Octadecadienoic acid</name>
  <description>10E, 12E-Octadecadienoic acid, also known as 10E, 12E-octadecadienoate or 10,12-linoleic acid, 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. 10E, 12E-Octadecadienoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.</description>
  <synonyms>
    <synonym>10,12-Linoleic acid</synonym>
    <synonym>10,12-Octadecadienoate</synonym>
    <synonym>10,12-Octadecadienoic acid</synonym>
    <synonym>10E, 12E-Octadecadienoate</synonym>
  </synonyms>
  <chemical_formula>C18H32O2</chemical_formula>
  <average_molecular_weight>280.452</average_molecular_weight>
  <monisotopic_moleculate_weight>280.24023027</monisotopic_moleculate_weight>
  <iupac_name>(10E,12E)-octadeca-10,12-dienoic acid</iupac_name>
  <traditional_iupac>(10E,12E)-octadeca-10,12-dienoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H]\C(CCCCC)=C(\[H])/C(/[H])=C(\[H])CCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-9H,2-5,10-17H2,1H3,(H,19,20)/b7-6+,9-8+</inchi>
  <inchikey>GKJZMAHZJGSBKD-BLHCBFLLSA-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>
    <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>
    <direct_parent>Lineolic acids and derivatives</direct_parent>
    <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>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state/>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(10E,12E)-octadeca-10,12-dienoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>280.452</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>280.24023027</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]\C(CCCCC)=C(\[H])/C(/[H])=C(\[H])CCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H32O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-9H,2-5,10-17H2,1H3,(H,19,20)/b7-6+,9-8+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GKJZMAHZJGSBKD-BLHCBFLLSA-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>88.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</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>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1241554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1241555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1241556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1356964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1356965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1356966</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>21.15</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>7.82</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>337.56</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>162.79</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>315.81</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>584.13</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id/>
  <pubchem_compound_id>5282801</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <foodb_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
