<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:34 UTC</creation_date>
  <update_date>2019-11-26 02:58:07 UTC</update_date>
  <accession>FDB002907</accession>
  <name>Glycerol trilinoleate</name>
  <description>Constituent of seed oils rich in linoleic acid, e.g., sunflower oil. Glycerol trilinoleate is found in fats and oils.</description>
  <synonyms>
    <synonym>(Z,Z)-9,12-octadecadienoic acid, 1,2,3-propanetriyl ester</synonym>
    <synonym>1-Linoleoyl-2-linoleoyl-3-linoleoyl-glycerol</synonym>
    <synonym>1,2,3-Propanetriol trilinoleate</synonym>
    <synonym>1,2,3-Propanetriol trilinoleic acid</synonym>
    <synonym>1,2,3-Propenetriol tri(9,12-octadecadienoate)</synonym>
    <synonym>1,2,3-Propenetriol tri(9,12-octadecadienoic acid)</synonym>
    <synonym>1,2,3-Tri-(9Z,12Z-octadecadienoyl)glycerol</synonym>
    <synonym>1,2,3-Tri-(9Z,12Z)-octadecadienoylglycerol</synonym>
    <synonym>9,12-Octadecadienoic acid (Z,Z)-, 1,2,3-propanetriyl ester</synonym>
    <synonym>Glycerol trilinoleate</synonym>
    <synonym>Glyceryl trilinoleate</synonym>
    <synonym>Glyceryl trilinoleic acid</synonym>
    <synonym>Linoleoyl triglyceride</synonym>
    <synonym>Propane-1,2,3-triyl tris((9Z,12Z)-octadeca-9,12-dienoate)</synonym>
    <synonym>TAG(18:2/18:2/18:2)</synonym>
    <synonym>TAG(18:2N6/18:2N6/18:2N6)</synonym>
    <synonym>TAG(18:2W6/18:2W6/18:2W6)</synonym>
    <synonym>TAG(54:6)</synonym>
    <synonym>TG</synonym>
    <synonym>TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</synonym>
    <synonym>TG(18:2/18:2/18:2)</synonym>
    <synonym>TG(18:2N6/18:2N6/18:2N6)</synonym>
    <synonym>TG(18:2omega6/18:2omega6/18:2omega6)</synonym>
    <synonym>TG(18:2W6/18:2W6/18:2W6)</synonym>
    <synonym>TG(54:6)</synonym>
    <synonym>Tracylglycerol(18:2/18:2/18:2)</synonym>
    <synonym>Tracylglycerol(18:2N6/18:2N6/18:2N6)</synonym>
    <synonym>Tracylglycerol(18:2omega6/18:2omega6/18:2omega6)</synonym>
    <synonym>Tracylglycerol(18:2W6/18:2W6/18:2W6)</synonym>
    <synonym>Tracylglycerol(54:6)</synonym>
    <synonym>Triacylglycerol(18:2/18:2/18:2)</synonym>
    <synonym>Triacylglycerol(54:6)</synonym>
    <synonym>Trilinolein</synonym>
  </synonyms>
  <chemical_formula>C57H98O6</chemical_formula>
  <average_molecular_weight>879.3844</average_molecular_weight>
  <monisotopic_moleculate_weight>878.736340868</monisotopic_moleculate_weight>
  <iupac_name>1-[(9E,12E)-octadeca-9,12-dienoyloxy]-3-[(9E,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (9Z,12Z)-octadeca-9,12-dienoate</iupac_name>
  <traditional_iupac>1-[(9E,12E)-octadeca-9,12-dienoyloxy]-3-[(9E,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (9Z,12Z)-octadeca-9,12-dienoate</traditional_iupac>
  <cas_registry_number>537-40-6</cas_registry_number>
  <smiles>CCCCC\C=C\C\C=C\CCCCCCCC(=O)OCC(COC(=O)CCCCCCC\C=C\C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC</smiles>
  <inchi>InChI=1S/C57H98O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h16-21,25-30,54H,4-15,22-24,31-53H2,1-3H3/b19-16-,20-17+,21-18-,28-25+,29-26+,30-27-</inchi>
  <inchikey>HBOQXIRUPVQLKX-VXACIKFCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.</description>
    <direct_parent>Triacylglycerols</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerolipids</class>
    <sub_class>Triradylcglycerols</sub_class>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lineolic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Octadecanoid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Triacyl-sn-glycerol</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>10.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-8.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.88e-06 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp -11°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>19.42</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-6.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>1-[(9E,12E)-octadeca-9,12-dienoyloxy]-3-[(9E,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (9Z,12Z)-octadeca-9,12-dienoate</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>879.3844</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>878.736340868</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CCCCC\C=C\C\C=C\CCCCCCCC(=O)OCC(COC(=O)CCCCCCC\C=C\C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C57H98O6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C57H98O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h16-21,25-30,54H,4-15,22-24,31-53H2,1-3H3/b19-16-,20-17+,21-18-,28-25+,29-26+,30-27-</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>HBOQXIRUPVQLKX-VXACIKFCSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>78.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>275.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>112.34</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>50</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146540</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB05474</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Fats and oils</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Milk (Cow)</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>29.19</average_value>
      <max_value>89.0</max_value>
      <min_value>0.26</min_value>
      <unit>uM</unit>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>2-acylglycerol O-acyltransferase 1</name>
      <uniprot_id>Q96PD6</uniprot_id>
      <uniprot_name/>
      <gene_name>MOGAT1</gene_name>
    </enzyme>
    <enzyme>
      <name>2-acylglycerol O-acyltransferase 2</name>
      <uniprot_id>Q3SYC2</uniprot_id>
      <uniprot_name/>
      <gene_name>MOGAT2</gene_name>
    </enzyme>
    <enzyme>
      <name>2-acylglycerol O-acyltransferase 3</name>
      <uniprot_id>Q86VF5</uniprot_id>
      <uniprot_name/>
      <gene_name>MOGAT3</gene_name>
    </enzyme>
    <enzyme>
      <name>Apolipoprotein A-I</name>
      <uniprot_id>P02647</uniprot_id>
      <uniprot_name/>
      <gene_name>APOA1</gene_name>
    </enzyme>
    <enzyme>
      <name>Apolipoprotein B-100</name>
      <uniprot_id>P04114</uniprot_id>
      <uniprot_name/>
      <gene_name>APOB</gene_name>
    </enzyme>
    <enzyme>
      <name>Apolipoprotein E</name>
      <uniprot_id>P02649</uniprot_id>
      <uniprot_name/>
      <gene_name>APOE</gene_name>
    </enzyme>
    <enzyme>
      <name>Carnitine O-palmitoyltransferase 1, liver isoform</name>
      <uniprot_id>P50416</uniprot_id>
      <uniprot_name/>
      <gene_name>CPT1A</gene_name>
    </enzyme>
    <enzyme>
      <name>Carnitine O-palmitoyltransferase 1, muscle isoform</name>
      <uniprot_id>Q92523</uniprot_id>
      <uniprot_name/>
      <gene_name>CPT1B</gene_name>
    </enzyme>
    <enzyme>
      <name>Carnitine O-palmitoyltransferase 2, mitochondrial</name>
      <uniprot_id>P23786</uniprot_id>
      <uniprot_name/>
      <gene_name>CPT2</gene_name>
    </enzyme>
    <enzyme>
      <name>Diacylglycerol O-acyltransferase 1</name>
      <uniprot_id>O75907</uniprot_id>
      <uniprot_name/>
      <gene_name>DGAT1</gene_name>
    </enzyme>
    <enzyme>
      <name>Diacylglycerol O-acyltransferase 2</name>
      <uniprot_id>Q96PD7</uniprot_id>
      <uniprot_name/>
      <gene_name>DGAT2</gene_name>
    </enzyme>
    <enzyme>
      <name>Endothelial lipase</name>
      <uniprot_id>Q9Y5X9</uniprot_id>
      <uniprot_name/>
      <gene_name>LIPG</gene_name>
    </enzyme>
    <enzyme>
      <name>Gastric triacylglycerol lipase</name>
      <uniprot_id>P07098</uniprot_id>
      <uniprot_name/>
      <gene_name>LIPF</gene_name>
    </enzyme>
    <enzyme>
      <name>Glycerol-3-phosphate acyltransferase 3</name>
      <uniprot_id>Q53EU6</uniprot_id>
      <uniprot_name/>
      <gene_name>AGPAT9</gene_name>
    </enzyme>
    <enzyme>
      <name>Hepatic triacylglycerol lipase</name>
      <uniprot_id>P11150</uniprot_id>
      <uniprot_name/>
      <gene_name>LIPC</gene_name>
    </enzyme>
    <enzyme>
      <name>Inactive pancreatic lipase-related protein 1</name>
      <uniprot_id>P54315</uniprot_id>
      <uniprot_name/>
      <gene_name>PNLIPRP1</gene_name>
    </enzyme>
    <enzyme>
      <name>Lipoprotein lipase</name>
      <uniprot_id>P06858</uniprot_id>
      <uniprot_name/>
      <gene_name>LPL</gene_name>
    </enzyme>
    <enzyme>
      <name>Liver carboxylesterase 1</name>
      <uniprot_id>P23141</uniprot_id>
      <uniprot_name/>
      <gene_name>CES1</gene_name>
    </enzyme>
    <enzyme>
      <name>Lysosomal acid lipase/cholesteryl ester hydrolase</name>
      <uniprot_id>P38571</uniprot_id>
      <uniprot_name/>
      <gene_name>LIPA</gene_name>
    </enzyme>
    <enzyme>
      <name>Monoglyceride lipase</name>
      <uniprot_id>Q99685</uniprot_id>
      <uniprot_name/>
      <gene_name>MGLL</gene_name>
    </enzyme>
    <enzyme>
      <name>Pancreatic lipase-related protein 2</name>
      <uniprot_id>P54317</uniprot_id>
      <uniprot_name/>
      <gene_name>PNLIPRP2</gene_name>
    </enzyme>
    <enzyme>
      <name>Pancreatic lipase-related protein 3</name>
      <uniprot_id>Q17RR3</uniprot_id>
      <uniprot_name/>
      <gene_name>PNLIPRP3</gene_name>
    </enzyme>
    <enzyme>
      <name>Pancreatic triacylglycerol lipase</name>
      <uniprot_id>P16233</uniprot_id>
      <uniprot_name/>
      <gene_name>PNLIP</gene_name>
    </enzyme>
    <enzyme>
      <name>Patatin-like phospholipase domain-containing protein 2</name>
      <uniprot_id>Q96AD5</uniprot_id>
      <uniprot_name/>
      <gene_name>PNPLA2</gene_name>
    </enzyme>
    <enzyme>
      <name>Patatin-like phospholipase domain-containing protein 3</name>
      <uniprot_id>Q9NST1</uniprot_id>
      <uniprot_name/>
      <gene_name>PNPLA3</gene_name>
    </enzyme>
    <enzyme>
      <name>Patatin-like phospholipase domain-containing protein 4</name>
      <uniprot_id>P41247</uniprot_id>
      <uniprot_name/>
      <gene_name>PNPLA4</gene_name>
    </enzyme>
    <enzyme>
      <name>Protein disulfide-isomerase</name>
      <uniprot_id>P07237</uniprot_id>
      <uniprot_name/>
      <gene_name>P4HB</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
