<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-10-03 18:40:51 UTC</creation_date>
  <update_date>2020-06-04 20:33:22 UTC</update_date>
  <accession>BMDB0006323</accession>
  <secondary_accessions>
    <accession>BMDB06323</accession>
  </secondary_accessions>
  <name>Tetracosapentaenoic acid (24:5n-3)</name>
  <description>Tetracosapentaenoic acid (24:5N-3), also known as 9Z,12Z,15Z,18Z,21Z-tetracosapentaenoate or 24:5 (N-3), belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Tetracosapentaenoic acid (24:5N-3) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Tetracosapentaenoic acid (24:5N-3) participates in a number of enzymatic reactions, within cattle. In particular, Tetracosapentaenoic acid (24:5N-3) can be biosynthesized from docosapentaenoic acid (22N-3) through the action of the enzyme elongation OF very long chain fatty acids protein 4. In addition, Tetracosapentaenoic acid (24:5N-3) can be converted into tetracosahexaenoic acid; which is catalyzed by the enzyme fatty acid desaturase 2. In cattle, tetracosapentaenoic acid (24:5N-3) is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway.</description>
  <synonyms>
    <synonym>24:5 (N-3)</synonym>
    <synonym>24:5 (Omega-3)</synonym>
    <synonym>9Z,12Z,15Z,18Z,21Z-Tetracosapentaenoic acid</synonym>
    <synonym>all-cis-Tetracosa-9,12,15,18,21-pentaenoic acid</synonym>
    <synonym>9Z,12Z,15Z,18Z,21Z-Tetracosapentaenoate</synonym>
    <synonym>all-cis-Tetracosa-9,12,15,18,21-pentaenoate</synonym>
    <synonym>Tetracosapentaenoate (24:5N-3)</synonym>
    <synonym>(9Z,12Z,15Z,18Z,21Z)-Tetracosapentaenate</synonym>
    <synonym>(9Z,12Z,15Z,18Z,21Z)-Tetracosapentaenoate</synonym>
    <synonym>(9Z,12Z,15Z,18Z,21Z)-Tetracosapentaenoic acid</synonym>
    <synonym>Tetracosapentaenate</synonym>
  </synonyms>
  <chemical_formula>C24H38O2</chemical_formula>
  <average_molecular_weight>358.5573</average_molecular_weight>
  <monisotopic_moleculate_weight>358.28718046</monisotopic_moleculate_weight>
  <iupac_name>(9Z,12Z,15Z,18Z,21Z)-tetracosa-9,12,15,18,21-pentaenoic acid</iupac_name>
  <traditional_iupac>(9Z,12Z,15Z,18Z,21Z)-tetracosa-9,12,15,18,21-pentaenoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C24H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-23H2,1H3,(H,25,26)/b4-3-,7-6-,10-9-,13-12-,16-15-</inchi>
  <inchikey>NPTIBOCVSPURCS-JLNKQSITSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Very long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</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>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</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>
      <substituent>Very long-chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>omega-3 fatty acid</external_descriptor>
      <external_descriptor>tetracosapentaenoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(9Z,12Z,15Z,18Z,21Z)-tetracosa-9,12,15,18,21-pentaenoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>358.5573</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>358.28718046</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H38O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-23H2,1H3,(H,25,26)/b4-3-,7-6-,10-9-,13-12-,16-15-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NPTIBOCVSPURCS-JLNKQSITSA-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>119.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>44.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>17</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>
    <pathway>
      <name>Alpha Linolenic Acid and Linoleic Acid Metabolism</name>
      <smpdb_id>SMP0087171</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2678536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2678537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2678538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3030089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3030090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3030091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>161711</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2203.276 +/- 529.902</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>948.245 +/- 390.454</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2091.718 +/- 446.233</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB023890</foodb_id>
  <chemspider_id>30776540</chemspider_id>
  <pubchem_compound_id>52921801</pubchem_compound_id>
  <chebi_id>77360</chebi_id>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-7421</meta_cyc_id>
  <bigg_id>2219655</bigg_id>
  <wikipedia_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP02859</protein_accession>
      <name>Elongation of very long chain fatty acids protein 5</name>
      <uniprot_id>Q2KJD9</uniprot_id>
      <gene_name>ELOVL5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
