<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:23:23 UTC</creation_date>
  <update_date>2025-11-19 02:43:02 UTC</update_date>
  <accession>FDB023021</accession>
  <name>beta-Glycerophosphoric acid</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) [HMDB]</description>
  <synonyms>
    <synonym>1,2,3-Propanetriol, 2-(dihydrogen ate)</synonym>
    <synonym>1,2,3-Propanetriol, 2-(dihydrogen ic acid)</synonym>
    <synonym>1,3-Hydroxy-2-propyl dihydrogen ate</synonym>
    <synonym>1,3-Hydroxy-2-propyl dihydrogen ic acid</synonym>
    <synonym>2-glyceroate</synonym>
    <synonym>2-glyceroic acid</synonym>
    <synonym>2-HYDROXY-1-(hydroxymethyl)ethyl dihydrogen ATE</synonym>
    <synonym>2-HYDROXY-1-(hydroxymethyl)ethyl dihydrogen ic acid</synonym>
    <synonym>b-glyceroate</synonym>
    <synonym>b-glyceroic acid</synonym>
    <synonym>beta-glyceroate</synonym>
    <synonym>beta-glyceroic acid</synonym>
    <synonym>beta-GlyceroOrate</synonym>
    <synonym>beta-glycerooric acid</synonym>
    <synonym>beta-Glycerophosphorate</synonym>
    <synonym>beta-Glycerophosphoric acid</synonym>
    <synonym>Glycerol 2-ate</synonym>
    <synonym>Glycerol 2-ic acid</synonym>
    <synonym>Glycerol-2-ate</synonym>
    <synonym>Glycerol-2-phosphate</synonym>
    <synonym>Glycerol-2-phosphic acid</synonym>
    <synonym>β-glyceroate</synonym>
    <synonym>β-glyceroic 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>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycerophosphates. Glycerophosphates are compounds containing a glycerol linked to a phosphate group.</description>
    <direct_parent>Glycerophosphates</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>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</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>Sn-glycerol-2-phosphate</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>glycerol monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <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::MsIr</type>
      <spectrum_id>1792</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122618</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122619</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122620</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122621</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122622</spectrum_id>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>122626</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122627</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122628</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>122629</spectrum_id>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>122636</spectrum_id>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::MsMs</type>
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      <type>Specdb::MsMs</type>
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      <spectrum_id>439210</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2235827</spectrum_id>
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      <spectrum_id>2237564</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2237891</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2239670</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2240049</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2241681</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2242136</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2243716</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2244185</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2245895</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2252913</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2253544</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2255039</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2255552</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2256951</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2450983</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2450984</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2450985</spectrum_id>
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  </spectra>
  <hmdb_id>HMDB02520</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id>G2H</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce330abdb8&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Anatidae</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anatidae</name_scientific>
      <ncbi_taxonomy_id>8830</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Beefalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus X Bison bison</name_scientific>
      <ncbi_taxonomy_id>297284</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Bison</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bison bison</name_scientific>
      <ncbi_taxonomy_id>9901</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Buffalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bubalus bubalis</name_scientific>
      <ncbi_taxonomy_id>89462</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cattle (Beef, Veal)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus</name_scientific>
      <ncbi_taxonomy_id>9913</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Chicken</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Gallus gallus</name_scientific>
      <ncbi_taxonomy_id>9031</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Columbidae (Dove, Pigeon)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columbidae</name_scientific>
      <ncbi_taxonomy_id>8930</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervidae</name_scientific>
      <ncbi_taxonomy_id>9850</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic goat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capra aegagrus hircus</name_scientific>
      <ncbi_taxonomy_id>9925</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic pig</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa domestica</name_scientific>
      <ncbi_taxonomy_id>9825</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Elk</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervus canadensis</name_scientific>
      <ncbi_taxonomy_id>1574408</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Emu</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Dromaius novaehollandiae</name_scientific>
      <ncbi_taxonomy_id>8790</ncbi_taxonomy_id>
    </food>
    <food>
      <name>European rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryctolagus</name_scientific>
      <ncbi_taxonomy_id>9984</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Greylag goose</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anser anser</name_scientific>
      <ncbi_taxonomy_id>8843</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Guinea hen</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Numida meleagris</name_scientific>
      <ncbi_taxonomy_id>8996</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Horse</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Equus caballus</name_scientific>
      <ncbi_taxonomy_id>9796</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mallard duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anas platyrhynchos</name_scientific>
      <ncbi_taxonomy_id>8839</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/>
    </food>
    <food>
      <name>Mountain hare</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lepus timidus</name_scientific>
      <ncbi_taxonomy_id>62621</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mule deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Odocoileus</name_scientific>
      <ncbi_taxonomy_id>9871</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Ostrich</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Struthio camelus</name_scientific>
      <ncbi_taxonomy_id>8801</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pheasant</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianus colchicus</name_scientific>
      <ncbi_taxonomy_id>9054</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Quail</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianidae</name_scientific>
      <ncbi_taxonomy_id>9005</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Leporidae</name_scientific>
      <ncbi_taxonomy_id>9979</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rock ptarmigan</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lagopus muta</name_scientific>
      <ncbi_taxonomy_id>64668</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sheep (Mutton, Lamb)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ovis aries</name_scientific>
      <ncbi_taxonomy_id>9940</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Squab</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columba</name_scientific>
      <ncbi_taxonomy_id>8931</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Turkey</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Meleagris gallopavo</name_scientific>
      <ncbi_taxonomy_id>9103</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Velvet duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Melanitta fusca</name_scientific>
      <ncbi_taxonomy_id>371864</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild boar</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa</name_scientific>
      <ncbi_taxonomy_id>9823</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
