<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:06:10 UTC</creation_date>
  <update_date>2025-11-18 22:55:46 UTC</update_date>
  <accession>FDB004293</accession>
  <name>Steridonic acid</name>
  <description>Stearidonic acid, also known as SDA or stearidonate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Stearidonic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is biosynthesized from linolenic acid by the enzyme delta-6-desaturase. Natural sources of this fatty acid are in the blackcurrant and echium, and the cyanobacterium spirulina (a rich source of vitamins and minerals). Stearidonic acid is found in dietary plant oils which are metabolized to longer-chain, more unsaturated (n-3) polyunsaturated fatty acids (PUFA). These oils appear to possess hypotriglyceridemic properties typically associated with fish oils (PMID: 15173404). Stearidonic acid may be used as a precursor to increase the eicosapentaenoic acid (EPA) content of human lipids and that combinations of gamma-linolenic acid and stearidonic acid can be used to manipulate the fatty acid compositions of lipid pools in subtle ways. Such effects may offer new strategies for manipulation of cell composition to influence cellular responses and functions in desirable ways (PMID: 15120716).</description>
  <synonyms>
  </synonyms>
  <chemical_formula>C18H28O2</chemical_formula>
  <average_molecular_weight>276.4137</average_molecular_weight>
  <monisotopic_moleculate_weight>276.20893014</monisotopic_moleculate_weight>
  <iupac_name>(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid</iupac_name>
  <traditional_iupac>stearidonic acid</traditional_iupac>
  <cas_registry_number>20290-75-9</cas_registry_number>
  <smiles>CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O</smiles>
  <inchi>InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12-</inchi>
  <inchikey>JIWBIWFOSCKQMA-LTKCOYKYSA-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>Polyunsaturated fatty acids</external_descriptor>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>octadecatetraenoic acid</external_descriptor>
      <external_descriptor>omega-3 fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.02e-04 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>5.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>4.92</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>276.4137</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>276.20893014</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C18H28O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12-</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>JIWBIWFOSCKQMA-LTKCOYKYSA-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>90.75</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>33.11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>12</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>15577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>39036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>162103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>103929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>103930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>103931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>170097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>170098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>170099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476242</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB0006547</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Anatidae</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anatidae</name_scientific>
      <ncbi_taxonomy_id>8830</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Beefalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus X Bison bison</name_scientific>
      <ncbi_taxonomy_id>297284</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Bison</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bison bison</name_scientific>
      <ncbi_taxonomy_id>9901</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Borage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Borago officinalis</name_scientific>
      <ncbi_taxonomy_id>13363</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Buffalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bubalus bubalis</name_scientific>
      <ncbi_taxonomy_id>89462</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cattle (Beef, Veal)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus</name_scientific>
      <ncbi_taxonomy_id>9913</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Chicken</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Gallus gallus</name_scientific>
      <ncbi_taxonomy_id>9031</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Columbidae (Dove, Pigeon)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columbidae</name_scientific>
      <ncbi_taxonomy_id>8930</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervidae</name_scientific>
      <ncbi_taxonomy_id>9850</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic goat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capra aegagrus hircus</name_scientific>
      <ncbi_taxonomy_id>9925</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic pig</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa domestica</name_scientific>
      <ncbi_taxonomy_id>9825</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Elk</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervus canadensis</name_scientific>
      <ncbi_taxonomy_id>1574408</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Emu</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Dromaius novaehollandiae</name_scientific>
      <ncbi_taxonomy_id>8790</ncbi_taxonomy_id>
    </food>
    <food>
      <name>European rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryctolagus</name_scientific>
      <ncbi_taxonomy_id>9984</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Greylag goose</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anser anser</name_scientific>
      <ncbi_taxonomy_id>8843</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Guinea hen</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Numida meleagris</name_scientific>
      <ncbi_taxonomy_id>8996</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Horse</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Equus caballus</name_scientific>
      <ncbi_taxonomy_id>9796</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mallard duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anas platyrhynchos</name_scientific>
      <ncbi_taxonomy_id>8839</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mountain hare</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lepus timidus</name_scientific>
      <ncbi_taxonomy_id>62621</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mule deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Odocoileus</name_scientific>
      <ncbi_taxonomy_id>9871</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Ostrich</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Struthio camelus</name_scientific>
      <ncbi_taxonomy_id>8801</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pheasant</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianus colchicus</name_scientific>
      <ncbi_taxonomy_id>9054</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Quail</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianidae</name_scientific>
      <ncbi_taxonomy_id>9005</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Leporidae</name_scientific>
      <ncbi_taxonomy_id>9979</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rock ptarmigan</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lagopus muta</name_scientific>
      <ncbi_taxonomy_id>64668</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sheep (Mutton, Lamb)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ovis aries</name_scientific>
      <ncbi_taxonomy_id>9940</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Squab</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columba</name_scientific>
      <ncbi_taxonomy_id>8931</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Turkey</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Meleagris gallopavo</name_scientific>
      <ncbi_taxonomy_id>9103</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Velvet duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Melanitta fusca</name_scientific>
      <ncbi_taxonomy_id>371864</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild boar</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa</name_scientific>
      <ncbi_taxonomy_id>9823</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
