<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-10-03 18:10:23 UTC</creation_date>
  <update_date>2020-05-21 16:28:09 UTC</update_date>
  <accession>BMDB0010616</accession>
  <secondary_accessions>
    <accession>BMDB10616</accession>
  </secondary_accessions>
  <name>PG(18:1(11Z)/16:1(9Z))</name>
  <description>PG(18:1(11Z)/16:1(9Z)), also known as GPG(18:1/16:1) or GPG(34:2), belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(18:1(11Z)/16:1(9Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). PG(18:1(11Z)/16:1(9Z)) exists in all living organisms, ranging from bacteria to humans. PG(18:1(11Z)/16:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, PG(18:1(11Z)/16:1(9Z)) can be biosynthesized from PGP(18:1(11Z)/16:1(9Z)) through its interaction with the enzyme phosphatidylglycerophosphatase and protein-tyrosine phosphatase 1. Furthermore, PG(18:1(11Z)/16:1(9Z)) and CDP-DG(18:1(11Z)/18:1(9Z)) can be converted into CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(9Z)) and cytidine monophosphate through its interaction with the enzyme cardiolipin synthase. Furthermore, PG(18:1(11Z)/16:1(9Z)) can be biosynthesized from PGP(18:1(11Z)/16:1(9Z)); which is mediated by the enzyme phosphatidylglycerophosphatase and protein-tyrosine phosphatase 1. Furthermore, PG(18:1(11Z)/16:1(9Z)) and CDP-DG(18:1(9Z)/16:1(9Z)) can be converted into CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:1(9Z)) and cytidine monophosphate; which is catalyzed by the enzyme cardiolipin synthase. Furthermore, PG(18:1(11Z)/16:1(9Z)) can be biosynthesized from PGP(18:1(11Z)/16:1(9Z)); which is catalyzed by the enzyme phosphatidylglycerophosphatase and protein-tyrosine phosphatase 1. Finally, PG(18:1(11Z)/16:1(9Z)) and CDP-DG(18:2(9Z,12Z)/18:2(9Z,12Z)) can be converted into CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) and cytidine monophosphate through the action of the enzyme cardiolipin synthase. In cattle, PG(18:1(11Z)/16:1(9Z)) is involved in a few metabolic pathways, which include cardiolipin biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(9Z)) pathway, cardiolipin biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:1(9Z)) pathway, and cardiolipin biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) pathway.</description>
  <synonyms>
    <synonym>1-(11Z-Octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)</synonym>
    <synonym>1-Vaccenoyl-2-palmitoleoyl-sn-glycero-3-phosphoglycerol</synonym>
    <synonym>GPG(18:1/16:1)</synonym>
    <synonym>GPG(18:1N7/16:1N7)</synonym>
    <synonym>GPG(18:1W7/16:1W7)</synonym>
    <synonym>GPG(34:2)</synonym>
    <synonym>PG(18:1/16:1)</synonym>
    <synonym>PG(18:1N7/16:1N7)</synonym>
    <synonym>PG(18:1W7/16:1W7)</synonym>
    <synonym>PG(34:2)</synonym>
    <synonym>Phosphatidylglycerol(18:1/16:1)</synonym>
    <synonym>Phosphatidylglycerol(18:1n7/16:1n7)</synonym>
    <synonym>Phosphatidylglycerol(18:1W7/16:1W7)</synonym>
    <synonym>Phosphatidylglycerol(34:2)</synonym>
    <synonym>1-(11Z-Octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoglycerol</synonym>
    <synonym>PG(18:1(11Z)/16:1(9Z))</synonym>
  </synonyms>
  <chemical_formula>C40H75O10P</chemical_formula>
  <average_molecular_weight>746.9913</average_molecular_weight>
  <monisotopic_moleculate_weight>746.509785132</monisotopic_moleculate_weight>
  <iupac_name>[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid</iupac_name>
  <traditional_iupac>(2S)-2,3-dihydroxypropoxy(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxyphosphinic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC</smiles>
  <inchi>InChI=1S/C40H75O10P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-39(43)47-35-38(36-49-51(45,46)48-34-37(42)33-41)50-40(44)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h13-16,37-38,41-42H,3-12,17-36H2,1-2H3,(H,45,46)/b15-13-,16-14-/t37-,38+/m0/s1</inchi>
  <inchikey>ICYKSOZJGJBBNU-GFJSAGKOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerophospholipids</class>
    <sub_class>Glycerophosphoglycerols</sub_class>
    <direct_parent>Phosphatidylglycerols</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Dialkyl phosphates</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diacylglycerophosphoglycerol</substituent>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dialkyl phosphate</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>8.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>11.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>746.9913</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>746.509785132</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C40H75O10P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C40H75O10P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-39(43)47-35-38(36-49-51(45,46)48-34-37(42)33-41)50-40(44)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h13-16,37-38,41-42H,3-12,17-36H2,1-2H3,(H,45,46)/b15-13-,16-14-/t37-,38+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ICYKSOZJGJBBNU-GFJSAGKOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>148.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>206.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>88.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>40</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</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>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078695</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2815102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2815103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2815104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>773800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>773801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>773802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>773803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>773804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>773805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>773806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>773807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>773808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>336637</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>All Tissues</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>
  <chemspider_id>24768115</chemspider_id>
  <pubchem_compound_id>53480615</pubchem_compound_id>
  <chebi_id>89271</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <foodb_id>FDB027766</foodb_id>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP02836</protein_accession>
      <name>Protein tyrosine phosphatase mitochondrial 1</name>
      <uniprot_id>Q2NKZ7</uniprot_id>
      <gene_name>PTPMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
