<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:04 UTC</creation_date>
  <update_date>2020-04-22 15:03:59 UTC</update_date>
  <accession>BMDB0000521</accession>
  <secondary_accessions>
    <accession>BMDB00521</accession>
  </secondary_accessions>
  <name>5Z-Tetradecenoic acid</name>
  <description>5-Tetradecenoic acid, also known as (Z)-5-tetradecenoate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 5-Tetradecenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-Tetradecenoic acid has been linked to the inborn metabolic disorders including very long chain acyl-coa dehydrogenase deficiency.</description>
  <synonyms>
    <synonym>(Z)-5-Tetradecenoic acid</synonym>
    <synonym>cis-5-Tetradecenoic acid</synonym>
    <synonym>(Z)-5-Tetradecenoate</synonym>
    <synonym>cis-5-Tetradecenoate</synonym>
    <synonym>5Z-Tetradecenoate</synonym>
    <synonym>5-Tetradecenoate</synonym>
    <synonym>(5Z)- 5-Tetradecenoate</synonym>
    <synonym>(5Z)- 5-Tetradecenoic acid</synonym>
    <synonym>cis-D5-Tetradecenoate</synonym>
    <synonym>cis-D5-Tetradecenoic acid</synonym>
    <synonym>Physeterate</synonym>
    <synonym>(5Z)-5-Tetradecenoic acid</synonym>
    <synonym>C14:1W9</synonym>
    <synonym>FA(14:1(5Z))</synonym>
    <synonym>FA(14:1n9)</synonym>
    <synonym>Physeteric acid</synonym>
    <synonym>Physoteric acid</synonym>
    <synonym>cis-Tetradec-5-enoate</synonym>
  </synonyms>
  <chemical_formula>C14H26O2</chemical_formula>
  <average_molecular_weight>226.355</average_molecular_weight>
  <monisotopic_moleculate_weight>226.193280076</monisotopic_moleculate_weight>
  <iupac_name>(5Z)-tetradec-5-enoic acid</iupac_name>
  <traditional_iupac>cis-5-tetradecenoic acid</traditional_iupac>
  <cas_registry_number>5684-70-8</cas_registry_number>
  <smiles>CCCCCCCC\C=C/CCCC(O)=O</smiles>
  <inchi>InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h9-10H,2-8,11-13H2,1H3,(H,15,16)/b10-9-</inchi>
  <inchikey>AFGUVBVUFZMJMX-KTKRTIGZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 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>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>Long-chain fatty acid</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>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>monounsaturated fatty acid</external_descriptor>
      <external_descriptor>tetradecenoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5Z)-tetradec-5-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>226.355</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>226.193280076</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCC\C=C/CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H26O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h9-10H,2-8,11-13H2,1H3,(H,15,16)/b10-9-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AFGUVBVUFZMJMX-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>69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</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>292096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2457836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2457837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2457838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2480878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2480879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2480880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>151146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1064813</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022089</foodb_id>
  <pubchem_compound_id>5312400</pubchem_compound_id>
  <chemspider_id>4471825</chemspider_id>
  <knapsack_id/>
  <chebi_id>70716</chebi_id>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5506</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Jin, Shiow Jen; Tserng, Kou Yi.  Metabolic origins of urinary unsaturated dicarboxylic acids.    Biochemistry  (1990),  29(37),  8540-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
