<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-07-30 14:54:59 -0600</creation_date>
  <update_date>2015-06-03 17:20:55 -0600</update_date>
  <accession>ECMDB21222</accession>
  <m2m_id>M2MDB001630</m2m_id>
  <name>Glycerol 2-phosphate</name>
  <description>Glycerol-2-phosphate is a component of glycerolipid metabolism.  It is formed in minor quanitites, as the alpha glycerophosphorate is preferentially formed in this manner.  Also used as a biological buffer (Sigma-Aldrich). </description>
  <synonyms>
    <synonym>&amp;beta;-glycerol-phosphate</synonym>
    <synonym>&amp;beta;-glycerol-phosphoric acid</synonym>
    <synonym>1,2,3-Propanetriol, 2-(dihydrogen phosphate)</synonym>
    <synonym>1,2,3-Propanetriol, 2-(dihydrogen phosphoric acid)</synonym>
    <synonym>1,3-Hydroxy-2-propyl dihydrogen phosphate</synonym>
    <synonym>1,3-Hydroxy-2-propyl dihydrogen phosphoric acid</synonym>
    <synonym>2-Glycerophosphate</synonym>
    <synonym>2-Glycerophosphoric acid</synonym>
    <synonym>2-HYDROXY-1-(HYDROXYMETHYL)ETHYL DIHYDROGEN PHOSPHATE</synonym>
    <synonym>2-HYDROXY-1-(hydroxymethyl)ethyl dihydrogen phosphoric acid</synonym>
    <synonym>B-Glycerol-phosphate</synonym>
    <synonym>b-Glycerol-phosphoric acid</synonym>
    <synonym>b-Glycerophosphate</synonym>
    <synonym>b-Glycerophosphorate</synonym>
    <synonym>b-Glycerophosphoric acid</synonym>
    <synonym>Beta-Glycerol-phosphate</synonym>
    <synonym>beta-Glycerol-phosphoric acid</synonym>
    <synonym>beta-Glycerophosphate</synonym>
    <synonym>Beta-Glycerophosphorate</synonym>
    <synonym>Beta-Glycerophosphoric acid</synonym>
    <synonym>Glycerol 2-(dihydrogen phosphate)</synonym>
    <synonym>Glycerol 2-(dihydrogen phosphoric acid)</synonym>
    <synonym>Glycerol 2-phosphate</synonym>
    <synonym>Glycerol 2-phosphoric acid</synonym>
    <synonym>Glycerol-2-phosphate</synonym>
    <synonym>Glycerol-2-phosphoric acid</synonym>
    <synonym>β-Glycerol-phosphate</synonym>
    <synonym>β-Glycerol-phosphoric acid</synonym>
    <synonym>β-Glycerophosphate</synonym>
    <synonym>β-Glycerophosphorate</synonym>
    <synonym>β-Glycerophosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C3H9O6P</chemical_formula>
  <average_molecular_weight>172.0737</average_molecular_weight>
  <monisotopic_moleculate_weight>172.013674532</monisotopic_moleculate_weight>
  <iupac_name>[(1,3-dihydroxypropan-2-yl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>β-glycerophosphorate</traditional_iupac>
  <cas_registry_number>17181-54-3</cas_registry_number>
  <smiles>OCC(CO)OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C3H9O6P/c4-1-3(2-5)9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)</inchi>
  <inchikey>DHCLVCXQIBBOPH-UHFFFAOYSA-N</inchikey>
  <state>Solid</state>
  <cellular_locations>
    <cellular_location>Cytosol</cellular_location>
    <cellular_location>Extra-organism</cellular_location>
    <cellular_location>Periplasm</cellular_location>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.07e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>1.13</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>[(1,3-dihydroxypropan-2-yl)oxy]phosphonic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>172.0737</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>172.013674532</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OCC(CO)OP(O)(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C3H9O6P</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C3H9O6P/c4-1-3(2-5)9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>DHCLVCXQIBBOPH-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>107.22</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>31.39</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>13.29</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>4</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>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>158135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2235827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2237564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2237891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2239670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2240049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2241681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2242136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2243716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2244185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2245895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2252913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2253544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2255039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2255552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2256951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2450983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2450984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2450985</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB02520</hmdb_id>
  <pubchem_compound_id>2526</pubchem_compound_id>
  <chemspider_id>2431</chemspider_id>
  <kegg_id>C02979</kegg_id>
  <chebi_id>17270</chebi_id>
  <biocyc_id>CPD-536</biocyc_id>
  <het_id>G2H</het_id>
  <wikipidia/>
  <foodb_id/>
  <general_references>
    <reference>
      <reference_text>van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.</reference_text>
      <pubmed_id>17765195</pubmed_id>
    </reference>
    <reference>
      <reference_text>Chamberlin BA, Sweeley CC: Metabolic profiles of urinary organic acids recovered from absorbent filter paper. Clin Chem. 1987 Apr;33(4):572-6.</reference_text>
      <pubmed_id>3829393</pubmed_id>
    </reference>
  </general_references>
  <synthesis_reference/>
  <msds_url/>
  <enzymes>
    <enzyme>
      <name>Inositol-1-monophosphatase</name>
      <uniprot_id>P0ADG4</uniprot_id>
      <uniprot_name>SUHB_ECOLI</uniprot_name>
      <gene_name>suhB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0ADG4.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Class B acid phosphatase</name>
      <uniprot_id>P0AE22</uniprot_id>
      <uniprot_name>APHA_ECOLI</uniprot_name>
      <gene_name>aphA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AE22.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>sn-glycerol-3-phosphate import ATP-binding protein UgpC</name>
      <uniprot_id>P10907</uniprot_id>
      <uniprot_name>UGPC_ECOLI</uniprot_name>
      <gene_name>ugpC</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P10907.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>sn-glycerol-3-phosphate transport system permease protein ugpA</name>
      <uniprot_id>P10905</uniprot_id>
      <uniprot_name>UGPA_ECOLI</uniprot_name>
      <gene_name>ugpA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P10905.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>sn-glycerol-3-phosphate transport system permease protein ugpE</name>
      <uniprot_id>P10906</uniprot_id>
      <uniprot_name>UGPE_ECOLI</uniprot_name>
      <gene_name>ugpE</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P10906.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>sn-glycerol-3-phosphate-binding periplasmic protein ugpB</name>
      <uniprot_id>P0AG80</uniprot_id>
      <uniprot_name>UGPB_ECOLI</uniprot_name>
      <gene_name>ugpB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AG80.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
    <enzyme>
      <name>sn-glycerol-3-phosphate import ATP-binding protein UgpC</name>
      <uniprot_id>P10907</uniprot_id>
      <uniprot_name>UGPC_ECOLI</uniprot_name>
      <gene_name>ugpC</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P10907.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>sn-glycerol-3-phosphate transport system permease protein ugpA</name>
      <uniprot_id>P10905</uniprot_id>
      <uniprot_name>UGPA_ECOLI</uniprot_name>
      <gene_name>ugpA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P10905.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>sn-glycerol-3-phosphate transport system permease protein ugpE</name>
      <uniprot_id>P10906</uniprot_id>
      <uniprot_name>UGPE_ECOLI</uniprot_name>
      <gene_name>ugpE</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P10906.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Outer membrane protein N</name>
      <uniprot_id>P77747</uniprot_id>
      <uniprot_name>OMPN_ECOLI</uniprot_name>
      <gene_name>ompN</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P77747.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Outer membrane pore protein E</name>
      <uniprot_id>P02932</uniprot_id>
      <uniprot_name>PHOE_ECOLI</uniprot_name>
      <gene_name>phoE</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P02932.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Outer membrane protein F</name>
      <uniprot_id>P02931</uniprot_id>
      <uniprot_name>OMPF_ECOLI</uniprot_name>
      <gene_name>ompF</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P02931.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>sn-glycerol-3-phosphate-binding periplasmic protein ugpB</name>
      <uniprot_id>P0AG80</uniprot_id>
      <uniprot_name>UGPB_ECOLI</uniprot_name>
      <gene_name>ugpB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AG80.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Outer membrane protein C</name>
      <uniprot_id>P06996</uniprot_id>
      <uniprot_name>OMPC_ECOLI</uniprot_name>
      <gene_name>ompC</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P06996.xml</protein_url>
    </enzyme>
  </transporters>
  <reactions>
    <reaction_text>Adenosine triphosphate + Water + Glycerol 2-phosphate &gt; ADP + Glycerol 2-phosphate + Hydrogen ion + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>TRANS-RXN0-477</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Water + Glycerol 2-phosphate &gt; ADP + Glycerol 2-phosphate + Hydrogen ion + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>TRANS-RXN0-477</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Glycerol 2-phosphate + Water &gt; Glycerol + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Glycerol 2-phosphate + Water + Adenosine triphosphate &gt; Glycerol 2-phosphate + ADP + Hydrogen ion + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>TRANS-RXN0-477</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Glycerol 2-phosphate + Water + Adenosine triphosphate &gt; Glycerol 2-phosphate + ADP + Hydrogen ion + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>TRANS-RXN0-477</ecocyc_id>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
