<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 01:32:09 UTC</creation_date>
  <update_date>2015-07-21 06:59:17 UTC</update_date>
  <accession>FDB027931</accession>
  <name>PA(20:4(5Z,8Z,11Z,14Z)e/2:0)</name>
  <description>2-Acetyl-1-(5Z,8Z,11Z,14Z-eicosatetraenyl)-sn-glycero-phosphate is an ether lipid.  Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. [HMDB]</description>
  <synonyms>
    <synonym>2-Acetyl-1-(5Z,8Z,11Z,14Z-eicosatetraenyl)-sn-glycero-ate</synonym>
    <synonym>2-Acetyl-1-(5Z,8Z,11Z,14Z-eicosatetraenyl)-sn-glycero-phosphate</synonym>
    <synonym>PA(o-20:4(5Z,8Z,11Z,14Z)/2:0)</synonym>
  </synonyms>
  <chemical_formula>C25H43O7P</chemical_formula>
  <average_molecular_weight>486.5785</average_molecular_weight>
  <monisotopic_moleculate_weight>486.274640242</monisotopic_moleculate_weight>
  <iupac_name>[(2R)-2-(acetyloxy)-3-(icosa-5,8,11,14-tetraen-1-yloxy)propoxy]phosphonic acid</iupac_name>
  <traditional_iupac>(2R)-2-(acetyloxy)-3-(icosa-5,8,11,14-tetraen-1-yloxy)propoxyphosphonic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@](COCCCCC=CCC=CCC=CCC=CCCCCC)(COP(O)(O)=O)OC(C)=O</smiles>
  <inchi>InChI=1S/C25H43O7P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-30-22-25(32-24(2)26)23-31-33(27,28)29/h7-8,10-11,13-14,16-17,25H,3-6,9,12,15,18-23H2,1-2H3,(H2,27,28,29)/t25-/m1/s1</inchi>
  <inchikey>LTIFQHVEGFEXBJ-RUZDIDTESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-alkyl,2-acylglycerophosphates. These are glycerophosphates  in which the O-1 atom of the glycerol is bonded to a fatty acid (saturated or unsaturated) through an ether linkage, and the O-2 atom is bonded to another fatty acid through an ester linkage.</description>
    <direct_parent>1-alkyl,2-acylglycerophosphates</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerophospholipids</class>
    <sub_class>Glycerophosphates</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>Dialkyl ethers</alternative_parent>
      <alternative_parent>Glycerol ethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-alkyl,2-acyl-glycerol-3-phosphate</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 ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Glycerol ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</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>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.22e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>6.11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>1.32</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>[(2R)-2-(acetyloxy)-3-(icosa-5,8,11,14-tetraen-1-yloxy)propoxy]phosphonic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>486.5785</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>486.274640242</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>[H][C@@](COCCCCC=CCC=CCC=CCC=CCCCCC)(COP(O)(O)=O)OC(C)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C25H43O7P</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C25H43O7P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-30-22-25(32-24(2)26)23-31-33(27,28)29/h7-8,10-11,13-14,16-17,25H,3-6,9,12,15,18-23H2,1-2H3,(H2,27,28,29)/t25-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>LTIFQHVEGFEXBJ-RUZDIDTESA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>102.29</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>137.25</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>54.43</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>22</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <hmdb_id>HMDB11156</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>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>1-acyl-sn-glycerol-3-phosphate acyltransferase alpha</name>
      <uniprot_id>Q99943</uniprot_id>
      <uniprot_name/>
      <gene_name>AGPAT1</gene_name>
    </enzyme>
    <enzyme>
      <name>1-acyl-sn-glycerol-3-phosphate acyltransferase beta</name>
      <uniprot_id>O15120</uniprot_id>
      <uniprot_name/>
      <gene_name>AGPAT2</gene_name>
    </enzyme>
    <enzyme>
      <name>1-acyl-sn-glycerol-3-phosphate acyltransferase delta</name>
      <uniprot_id>Q9NRZ5</uniprot_id>
      <uniprot_name/>
      <gene_name>AGPAT4</gene_name>
    </enzyme>
    <enzyme>
      <name>1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon</name>
      <uniprot_id>Q9NUQ2</uniprot_id>
      <uniprot_name/>
      <gene_name>AGPAT5</gene_name>
    </enzyme>
    <enzyme>
      <name>1-acyl-sn-glycerol-3-phosphate acyltransferase gamma</name>
      <uniprot_id>Q9NRZ7</uniprot_id>
      <uniprot_name/>
      <gene_name>AGPAT3</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>Lipid phosphate phosphatase-related protein type 4</name>
      <uniprot_id>Q7Z2D5</uniprot_id>
      <uniprot_name/>
      <gene_name>LPPR4</gene_name>
    </enzyme>
    <enzyme>
      <name>Lipid phosphate phosphatase-related protein type 5</name>
      <uniprot_id>Q32ZL2</uniprot_id>
      <uniprot_name/>
      <gene_name>LPPR5</gene_name>
    </enzyme>
    <enzyme>
      <name>Lysocardiolipin acyltransferase 1</name>
      <uniprot_id>Q6UWP7</uniprot_id>
      <uniprot_name/>
      <gene_name>LCLAT1</gene_name>
    </enzyme>
    <enzyme>
      <name>Phosphatidate phosphatase PPAPDC1A</name>
      <uniprot_id>Q5VZY2</uniprot_id>
      <uniprot_name/>
      <gene_name>PPAPDC1A</gene_name>
    </enzyme>
    <enzyme>
      <name>Phosphatidate phosphatase PPAPDC1B</name>
      <uniprot_id>Q8NEB5</uniprot_id>
      <uniprot_name/>
      <gene_name>PPAPDC1B</gene_name>
    </enzyme>
    <enzyme>
      <name>Phospholipase DDHD1</name>
      <uniprot_id>Q8NEL9</uniprot_id>
      <uniprot_name/>
      <gene_name>DDHD1</gene_name>
    </enzyme>
    <enzyme>
      <name>Phospholipase DDHD2</name>
      <uniprot_id>O94830</uniprot_id>
      <uniprot_name/>
      <gene_name>DDHD2</gene_name>
    </enzyme>
    <enzyme>
      <name>Presqualene diphosphate phosphatase</name>
      <uniprot_id>Q8IY26</uniprot_id>
      <uniprot_name/>
      <gene_name>PPAPDC2</gene_name>
    </enzyme>
    <enzyme>
      <name>Probable lipid phosphate phosphatase PPAPDC3</name>
      <uniprot_id>Q8NBV4</uniprot_id>
      <uniprot_name/>
      <gene_name>PPAPDC3</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
