<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-05-31 14:00:23 -0600</creation_date>
  <update_date>2015-06-03 15:54:32 -0600</update_date>
  <accession>ECMDB03840</accession>
  <m2m_id>M2MDB000525</m2m_id>
  <name>Phosphoroselenoic acid</name>
  <description>Phosphoroselenoic acid, H3SePO3, is the activated selenium donor compound required for the biosynthesis of selenocysteyl-tRNA, the precursor of specific selenocysteine residues in bacterial and mammalian selenoproteins. Selenocysteine is often called the 21st amino acid, because Sec has a specific tRNA and codon UGA, and shares a major stop codon UGA. A number of enzymes have selenocysteine, residues and in some cases at their active sites. Proteins containing the 21st amino acid, selenocysteine (Sec), have been described in all three domains of life. (PMID: 18156471)</description>
  <synonyms>
    <synonym>Monoselenophosphate</synonym>
    <synonym>Monoselenophosphorate</synonym>
    <synonym>Monoselenophosphoric acid</synonym>
    <synonym>Phosphoroselenoate</synonym>
    <synonym>Selenophosphate</synonym>
    <synonym>Selenophosphorate</synonym>
    <synonym>Selenophosphoric acid</synonym>
    <synonym>SePO3</synonym>
    <synonym>Trihydroxidoselenidophosphorus</synonym>
    <synonym>[P(OH)3Se]</synonym>
  </synonyms>
  <chemical_formula>H3O3PSe</chemical_formula>
  <average_molecular_weight>160.96</average_molecular_weight>
  <monisotopic_moleculate_weight>161.898502302</monisotopic_moleculate_weight>
  <iupac_name>hydroxy(selanylidene)phosphonous acid</iupac_name>
  <traditional_iupac>selenophosphoric acid</traditional_iupac>
  <cas_registry_number>25758-66-1</cas_registry_number>
  <smiles>OP(O)(O)=[Se]</smiles>
  <inchi>InChI=1S/H3O3PSe/c1-4(2,3)5/h(H3,1,2,3,5)</inchi>
  <inchikey>JRPHGDYSKGJTKZ-UHFFFAOYSA-N</inchikey>
  <state>Solid</state>
  <cellular_locations>
    <cellular_location>Cytosol</cellular_location>
  </cellular_locations>
  <predicted_properties>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-1.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>-6.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>hydroxy(selanylidene)phosphonous acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>160.96</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>161.898502302</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OP(O)(O)=[Se]</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>H3O3PSe</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/H3O3PSe/c1-4(2,3)5/h(H3,1,2,3,5)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>JRPHGDYSKGJTKZ-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>60.69</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>26.32</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>7.23</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
    <pathway>
      <name>Selenoamino acid metabolism</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00450</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Aminoacyl-tRNA biosynthesis</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00970</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Metabolic pathways</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>eco01100</kegg_map_id>
      <subject/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>136167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>143901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2733900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2733901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2733902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2971608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2971609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2971610</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB03840</hmdb_id>
  <pubchem_compound_id>1092</pubchem_compound_id>
  <chemspider_id>1061</chemspider_id>
  <kegg_id>C05172</kegg_id>
  <chebi_id>16144</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <foodb_id/>
  <general_references>
    <reference>
      <reference_text>Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.</reference_text>
      <pubmed_id>22080510</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lobanov, A. V., Hatfield, D. L., Gladyshev, V. N. (2008). "Selenoproteinless animals: selenophosphate synthetase SPS1 functions in a pathway unrelated to selenocysteine biosynthesis." Protein Sci 17:176-182.</reference_text>
      <pubmed_id>18156471</pubmed_id>
    </reference>
  </general_references>
  <synthesis_reference>Ephraim, F.; Majler, E.  Selenophosphates.    Berichte der Deutschen Chemischen Gesellschaft  (1910),  43  277-85. </synthesis_reference>
  <msds_url/>
  <enzymes>
    <enzyme>
      <name>L-seryl-tRNA(Sec) selenium transferase</name>
      <uniprot_id>P0A821</uniprot_id>
      <uniprot_name>SELA_ECOLI</uniprot_name>
      <gene_name>selA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0A821.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Selenide, water dikinase</name>
      <uniprot_id>P16456</uniprot_id>
      <uniprot_name>SELD_ECOLI</uniprot_name>
      <gene_name>selD</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P16456.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>tRNA 2-selenouridine synthase</name>
      <uniprot_id>P33667</uniprot_id>
      <uniprot_name>SELU_ECOLI</uniprot_name>
      <gene_name>selU</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P33667.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
  </transporters>
  <reactions>
    <reaction_text>Adenosine triphosphate + Water + Selenium &gt; Adenosine monophosphate + Phosphate + Phosphoroselenoic acid</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Phosphoroselenoic acid &gt; Hydrogen ion + Phosphate + L-Selenocysteinyl-tRNA(Sec)</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Hydrogen selenide + Water &lt;&gt; Adenosine monophosphate + Phosphoroselenoic acid + Phosphate</reaction_text>
    <kegg_reaction_id>R03595</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>L-Seryl-tRNA(Sec) + Phosphoroselenoic acid + L-Seryl-tRNA(Sec) &lt;&gt; L-Selenocysteinyl-tRNA(Sec) + Phosphate + L-Selenocysteinyl-tRNA(Sec)</reaction_text>
    <kegg_reaction_id>R08219</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>L-seryl-tRNA(Sec) + Phosphoroselenoic acid &gt; L-selenocysteinyl-tRNA(Sec) + Inorganic phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Hydrogen selenide + Water &gt; Adenosine monophosphate + Phosphoroselenoic acid + Inorganic phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>5-Methylaminomethyl-2-thiouridine + Phosphoroselenoic acid &gt; 5-Methylaminomethyl-2-selenouridine + Inorganic phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Hydrogen selenide + Water &lt;&gt; Adenosine monophosphate + Phosphoroselenoic acid + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>L-Seryl-tRNA(Sec) + Phosphoroselenoic acid &lt;&gt; L-Selenocysteinyl-tRNA(Sec) + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
