<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-05-31 14:36:46 -0600</creation_date>
  <update_date>2015-09-16 14:50:11 -0600</update_date>
  <accession>ECMDB20276</accession>
  <m2m_id>M2MDB001116</m2m_id>
  <name>O-Phospho-D-serine</name>
  <description>O-phospho-D-serine is a phosphoric ester of serine and phosphoric acid. Phosphorylated serine residues are often referred to as phosphoserine.  Phosphoserine is a component of many proteins. The phosphorylation of the alcohol functional group in serine to produce phosphoserine is catalyzed by various types of kinases.  Free phosphoserine may be found after proteins have been proteolyzed.  Phosphoserine phosphatase is able to dephosphorylate phosphoserince (both L and D forms).
</description>
  <synonyms>
    <synonym>(2S)-2-amino-3-phosphonooxypropanoate</synonym>
    <synonym>(2S)-2-amino-3-phosphonooxypropanoic acid</synonym>
    <synonym>2-Amino-3-(phosphonooxy)propanoate</synonym>
    <synonym>2-Amino-3-(phosphonooxy)propanoic acid</synonym>
    <synonym>3-P-Serine</synonym>
    <synonym>3-Phospho-1-serine</synonym>
    <synonym>3-Phospho-L-serine</synonym>
    <synonym>3-Phospho-serine</synonym>
    <synonym>3-Phosphoserine</synonym>
    <synonym>D -2-Amino-3-hydroxypropanoate 3-phosphate</synonym>
    <synonym>D -2-Amino-3-hydroxypropanoic acid 3-phosphate</synonym>
    <synonym>D -2-amino-3-Hydroxypropanoic acid 3-phosphoric acid</synonym>
    <synonym>D-O-Phosphoserine</synonym>
    <synonym>DL-2-Amino-3-hydroxypropanoate 3-phosphate</synonym>
    <synonym>DL-2-Amino-3-hydroxypropanoic acid 3-phosphate</synonym>
    <synonym>DL-2-amino-3-Hydroxypropanoic acid 3-phosphoric acid</synonym>
    <synonym>DL-O-phosphorylserine</synonym>
    <synonym>DL-O-phosphoserine</synonym>
    <synonym>DL-O-serine phosphate</synonym>
    <synonym>DL-O-Serine phosphoric acid</synonym>
    <synonym>DL-phosphoserine</synonym>
    <synonym>DL-serine dihydrogen phosphate</synonym>
    <synonym>DL-Serine dihydrogen phosphoric acid</synonym>
    <synonym>DL-Serine monophosphate</synonym>
    <synonym>DL-serine monophosphorate</synonym>
    <synonym>DL-serine monophosphoric acid</synonym>
    <synonym>DL-serine, dihydrogen phosphate (ester)</synonym>
    <synonym>DL-Serine, dihydrogen phosphoric acid (ester)</synonym>
    <synonym>DL-sop</synonym>
    <synonym>Energoserina</synonym>
    <synonym>L-Serine, dihydrogen phosphate</synonym>
    <synonym>L-Serine, dihydrogen phosphoric acid</synonym>
    <synonym>O-Phospho-DL-serine</synonym>
    <synonym>O-Phospho-L-serine</synonym>
    <synonym>O-Phosphono-Serine</synonym>
    <synonym>O-Phosphonoserine</synonym>
    <synonym>O-Phosphoserine</synonym>
    <synonym>P-Ser</synonym>
    <synonym>P-Serine</synonym>
    <synonym>Phosphonoserine</synonym>
    <synonym>Phosphorylserine</synonym>
    <synonym>Phosphoserine</synonym>
    <synonym>Serine phosphate</synonym>
    <synonym>Serine phosphoric acid</synonym>
    <synonym>Serine, dihydrogen phosphate (ester) (9CI)</synonym>
    <synonym>Serine, dihydrogen phosphate (ester), DL- (8CI)</synonym>
    <synonym>Serine, dihydrogen phosphoric acid (ester) (9ci)</synonym>
    <synonym>Serine, dihydrogen phosphoric acid (ester), DL- (8ci)</synonym>
    <synonym>Serine-3-p</synonym>
    <synonym>Serine-3-phosphate</synonym>
    <synonym>Serine-3-phosphoric acid</synonym>
    <synonym>Serophen</synonym>
    <synonym>Seryl phosphate</synonym>
    <synonym>Seryl phosphoric acid</synonym>
    <synonym>[1-14c] Serine Dihydrogen Phosphate (ester)</synonym>
    <synonym>[1-14C] Serine dihydrogen phosphoric acid (ester)</synonym>
  </synonyms>
  <chemical_formula>C3H8NO6P</chemical_formula>
  <average_molecular_weight>185.0725</average_molecular_weight>
  <monisotopic_moleculate_weight>185.008923505</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-amino-3-(phosphonooxy)propanoic acid</iupac_name>
  <traditional_iupac>O-phospho-D-serine</traditional_iupac>
  <cas_registry_number>17885-08-4</cas_registry_number>
  <smiles>[H][C@@](N)(COP(O)(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1</inchi>
  <inchikey>BZQFBWGGLXLEPQ-UWTATZPHSA-N</inchikey>
  <state>Solid</state>
  <cellular_locations>
    <cellular_location>Cytoplasm</cellular_location>
    <cellular_location>Periplasm</cellular_location>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.99e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>228 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-3.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>1.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>9.39</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2R)-2-amino-3-(phosphonooxy)propanoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>185.0725</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>185.008923505</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>[H][C@@](N)(COP(O)(O)=O)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C3H8NO6P</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>BZQFBWGGLXLEPQ-UWTATZPHSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>130.08</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>32.91</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>14.06</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>6</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>
    <pathway>
      <name>Glycine, serine and threonine metabolism</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00260</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Methane metabolism</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00680</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Microbial metabolism in diverse environments</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec01120</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>1085320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>333697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3608065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3608066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3608067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3608068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3608069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3608070</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id>106</pubchem_compound_id>
  <chemspider_id>388807</chemspider_id>
  <kegg_id>C02532</kegg_id>
  <chebi_id>37713</chebi_id>
  <biocyc_id>CPD-3722</biocyc_id>
  <het_id/>
  <wikipidia/>
  <foodb_id/>
  <general_references>
    <reference>
      <reference_text>Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.</reference_text>
      <pubmed_id>21097882</pubmed_id>
    </reference>
    <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>
  </general_references>
  <synthesis_reference></synthesis_reference>
  <msds_url/>
  <enzymes>
    <enzyme>
      <name>Phosphoserine phosphatase</name>
      <uniprot_id>P0AGB0</uniprot_id>
      <uniprot_name>SERB_ECOLI</uniprot_name>
      <gene_name>serB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AGB0.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
  </transporters>
  <reactions>
    <reaction_text>O-Phospho-D-serine + Water &gt; L-Serine + Inorganic phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Phosphoserine + O-Phospho-D-serine + Water &lt;&gt; L-Serine + D-Serine + Phosphate</reaction_text>
    <kegg_reaction_id>R00582 R02853 </kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
