<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2018-08-27 17:29:51 UTC</creation_date>
  <update_date>2020-06-04 22:03:15 UTC</update_date>
  <accession>BMDB0062589</accession>
  <secondary_accessions>
    <accession>BMDB62589</accession>
  </secondary_accessions>
  <name>11Z-hexadecenoic acid</name>
  <description>11Z-Hexadecenoic acid, also known as (Z)-11-hexadecenoate, 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. 11Z-Hexadecenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.</description>
  <synonyms>
    <synonym>(Z)-11-Hexadecenoic acid</synonym>
    <synonym>11-Hexadecenoic acid</synonym>
    <synonym>(Z)-11-Hexadecenoate</synonym>
    <synonym>11-Hexadecenoate</synonym>
    <synonym>11Z-Hexadecenoate</synonym>
    <synonym>cis-Palmitvaccenate</synonym>
    <synonym>(11Z)-Hexadecenoic acid</synonym>
    <synonym>FA(16:1(11Z))</synonym>
    <synonym>(11Z)-11-Hexadecenoic acid</synonym>
    <synonym>Hexadec-11(Z)-enoic acid</synonym>
    <synonym>cis-11-Hexadecenoic acid</synonym>
    <synonym>delta11-Hexadecenoic acid</synonym>
    <synonym>Δ11-Hexadecenoic acid</synonym>
  </synonyms>
  <chemical_formula>C16H30O2</chemical_formula>
  <average_molecular_weight>254.414</average_molecular_weight>
  <monisotopic_moleculate_weight>254.224580206</monisotopic_moleculate_weight>
  <iupac_name>(11Z)-hexadec-11-enoic acid</iupac_name>
  <traditional_iupac>11-hexadecenoic acid</traditional_iupac>
  <cas_registry_number>2271-34-3</cas_registry_number>
  <smiles>CCCC\C=C/CCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h5-6H,2-4,7-15H2,1H3,(H,17,18)/b6-5-</inchi>
  <inchikey>JGMYDQCXGIMHLL-WAYWQWQTSA-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>hexadecenoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state/>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(11Z)-hexadec-11-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>254.414</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>254.224580206</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCC\C=C/CCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H30O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h5-6H,2-4,7-15H2,1H3,(H,17,18)/b6-5-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JGMYDQCXGIMHLL-WAYWQWQTSA-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>78.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</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::CMs</type>
      <spectrum_id>36061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>909259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>909260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>909261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>956017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>956018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>956019</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>13088.9</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Calf-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>11320.13</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. With growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>12656.54</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Without growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>10600.83</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Yearling-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>310.83</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>236.94</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>1488.44</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>1794.52</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>9399.6</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>10946.49</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/>
      <comment>Two pasteurized milk brands from the Middle Eastern Region of Paraná State By Gas Chromatography (n = 15)</comment>
      <references>
        <reference>
          <reference_text>Julliana Isabelle Simionato, Juliana Carla Garcia, Geraldo Tadeu dos Santos, Cláudio Celestino Oliveira, Jesui Vergilio Visentainera and Nilson Evelázio de Souza. Validation of the Determination of Fatty Acids in Milk by Gas Chromatography. J. Braz. Chem. Soc., Vol. 21, No. 3, 520-524, 2010.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id/>
  <pubchem_compound_id>5312414</pubchem_compound_id>
  <chebi_id>35464</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <foodb_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Julliana Isabelle Simionato, Juliana Carla Garcia, Geraldo Tadeu dos Santos, Cláudio Celestino Oliveira, Jesui Vergilio Visentainera and Nilson Evelázio de Souza. Validation of the Determination of Fatty Acids in Milk by Gas Chromatography. J. Braz. Chem. Soc., Vol. 21, No. 3, 520-524, 2010.</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
