<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:54:41 UTC</creation_date>
  <update_date>2020-05-11 20:40:06 UTC</update_date>
  <accession>BMDB0002368</accession>
  <secondary_accessions>
    <accession>BMDB02368</accession>
  </secondary_accessions>
  <name>Nervonic acid</name>
  <description/>
  <synonyms>
    <synonym>(Z)-15-Tetracosenoic acid</synonym>
    <synonym>(Z)-Tetracos-15-enoic acid</synonym>
    <synonym>15cis-Tetracosenoic acid</synonym>
    <synonym>cis-15-Tetracosenoic acid</synonym>
    <synonym>cis-Delta(15)-Tetracosenoic acid</synonym>
    <synonym>Nervonsaeure</synonym>
    <synonym>Selacholeic acid</synonym>
    <synonym>(Z)-15-Tetracosenoate</synonym>
    <synonym>(Z)-Tetracos-15-enoate</synonym>
    <synonym>15cis-Tetracosenoate</synonym>
    <synonym>cis-15-Tetracosenoate</synonym>
    <synonym>cis-delta(15)-Tetracosenoate</synonym>
    <synonym>cis-Δ(15)-tetracosenoate</synonym>
    <synonym>cis-Δ(15)-tetracosenoic acid</synonym>
    <synonym>Selacholeate</synonym>
    <synonym>Nervonate</synonym>
    <synonym>(15Z)-Tetracos-15-enoate</synonym>
    <synonym>(15Z)-Tetracos-15-enoic acid</synonym>
    <synonym>(15Z)-Tetracosenoate</synonym>
    <synonym>(15Z)-Tetracosenoic acid</synonym>
    <synonym>15-Tetracosenoate</synonym>
    <synonym>15-Tetracosenoic acid</synonym>
    <synonym>15Z-Tetracosenoate</synonym>
    <synonym>15Z-Tetracosenoic acid</synonym>
    <synonym>cis-15-Teracosenoate</synonym>
    <synonym>cis-15-Teracosenoic acid</synonym>
    <synonym>cis-15-Tetracosenate</synonym>
    <synonym>cis-15-Tetracosenic acid</synonym>
    <synonym>cis-Selacholeate</synonym>
    <synonym>cis-Selacholeic acid</synonym>
    <synonym>trans-Tetracos-15-enoic acid</synonym>
    <synonym>(15Z)-15-Tetracosenoic acid</synonym>
    <synonym>FA(24:1(15Z))</synonym>
    <synonym>FA(24:1n9)</synonym>
    <synonym>Nevonic acid</synonym>
    <synonym>Nervonic acid</synonym>
  </synonyms>
  <chemical_formula>C24H46O2</chemical_formula>
  <average_molecular_weight>366.6208</average_molecular_weight>
  <monisotopic_moleculate_weight>366.349780716</monisotopic_moleculate_weight>
  <iupac_name>(15Z)-tetracos-15-enoic acid</iupac_name>
  <traditional_iupac>nervonic acid</traditional_iupac>
  <cas_registry_number>506-37-6</cas_registry_number>
  <smiles>CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C24H46O2/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/h9-10H,2-8,11-23H2,1H3,(H,25,26)/b10-9-</inchi>
  <inchikey>GWHCXVQVJPWHRF-KTKRTIGZSA-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>Monounsaturated fatty acids</external_descriptor>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>tetracosenoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>9.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>9.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(15Z)-tetracos-15-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>366.6208</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>366.349780716</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H46O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H46O2/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/h9-10H,2-8,11-23H2,1H3,(H,25,26)/b10-9-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GWHCXVQVJPWHRF-KTKRTIGZSA-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>115.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>49.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>21</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::NmrTwoD</type>
      <spectrum_id>1821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>135645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>143379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2236959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2842995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2842996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2842997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2865429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2865430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2865431</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Placenta</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB002934</foodb_id>
  <chemspider_id>4444565</chemspider_id>
  <pubchem_compound_id>5281120</pubchem_compound_id>
  <chebi_id>44247</chebi_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <kegg_id>C08323</kegg_id>
  <drugbank_id/>
  <knapsack_id>C00001230</knapsack_id>
  <meta_cyc_id/>
  <bigg_id>2218012</bigg_id>
  <wikipedia_id>Nervonic acid</wikipedia_id>
  <metlin_id>262</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
