<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-07-30 14:55:05 -0600</creation_date>
  <update_date>2015-10-02 02:25:53 -0600</update_date>
  <accession>ECMDB21238</accession>
  <m2m_id>M2MDB001646</m2m_id>
  <name>L-Threonine O-3-phosphate</name>
  <description>In E. coli, acid phosphatase / phosphotransferase and alkaline phosphatase are the enzymes that catalyze the chemical reaction L-threonine 3-O-phosphate[periplasmic space] + H2O[periplasmic space] -&gt; L-threonine[periplasmic space] + phosphate[periplasmic space], where L-Threonine O-3-phosphate is a substrate (EcoCyc compound: L-THREONINE-O-3-PHOSPHATE).</description>
  <synonyms>
    <synonym>(2S,3R)-2-amino-3-hydroxybutanoate</synonym>
    <synonym>(2S,3R)-2-amino-3-hydroxybutanoate 3-phosphate</synonym>
    <synonym>(2S,3R)-2-amino-3-hydroxybutanoic acid</synonym>
    <synonym>(2S,3R)-2-amino-3-hydroxybutanoic acid 3-phosphate</synonym>
    <synonym>(2S,3R)-2-amino-3-Hydroxybutanoic acid 3-phosphoric acid</synonym>
    <synonym>L-Threonine O-3-phosphate</synonym>
    <synonym>L-Threonine O-3-phosphoric acid</synonym>
    <synonym>L-Threonine O-phosphate</synonym>
    <synonym>L-Threonine O-phosphoric acid</synonym>
    <synonym>L-Threonine phosphate</synonym>
    <synonym>L-Threonine phosphoric acid</synonym>
    <synonym>O-Phospho-L-threonine</synonym>
    <synonym>O-Phosphono-L-threonine</synonym>
    <synonym>O3-phosphothreonine</synonym>
    <synonym>Phospho-L-threonine</synonym>
    <synonym>Phosphothreonine</synonym>
    <synonym>Synonyms    Sources</synonym>
    <synonym>Threonine phosphate ester</synonym>
    <synonym>Threonine phosphoric acid ester</synonym>
    <synonym>Threoninium dihydrogen phosphate</synonym>
    <synonym>Threoninium dihydrogen phosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C4H10NO6P</chemical_formula>
  <average_molecular_weight>199.0991</average_molecular_weight>
  <monisotopic_moleculate_weight>199.024573569</monisotopic_moleculate_weight>
  <iupac_name>(2S,3R)-2-amino-3-(phosphonooxy)butanoic acid</iupac_name>
  <traditional_iupac>phosphothreonine</traditional_iupac>
  <cas_registry_number>1114-81-4</cas_registry_number>
  <smiles>C[C@@H](OP(O)(O)=O)[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C4H10NO6P/c1-2(3(5)4(6)7)11-12(8,9)10/h2-3H,5H2,1H3,(H,6,7)(H2,8,9,10)/t2-,3+/m1/s1</inchi>
  <inchikey>USRGIUJOYOXOQJ-GBXIJSLDSA-N</inchikey>
  <state>Solid</state>
  <cellular_locations>
    <cellular_location>Extra-organism</cellular_location>
    <cellular_location>Periplasm</cellular_location>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.35e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-2.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>1.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>9.47</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2S,3R)-2-amino-3-(phosphonooxy)butanoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>199.0991</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>199.024573569</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>C[C@@H](OP(O)(O)=O)[C@H](N)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C4H10NO6P</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C4H10NO6P/c1-2(3(5)4(6)7)11-12(8,9)10/h2-3H,5H2,1H3,(H,6,7)(H2,8,9,10)/t2-,3+/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>USRGIUJOYOXOQJ-GBXIJSLDSA-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>37.33</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>15.43</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>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>39592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>138005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>145739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>93311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2757513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2757514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2757515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2947995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2947996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2947997</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB11185</hmdb_id>
  <pubchem_compound_id>3246323</pubchem_compound_id>
  <chemspider_id>2497038</chemspider_id>
  <kegg_id>C12147</kegg_id>
  <chebi_id>37525</chebi_id>
  <biocyc_id>L-THREONINE-O-3-PHOSPHATE</biocyc_id>
  <het_id>TPO</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>Kataoka, H., Nakai, K., Katagiri, Y., Makita, M. (1993). "Analysis of free and bound O-phosphoamino acids in urine by gas chromatography with flame photometric detection." Biomed Chromatogr 7:184-188.</reference_text>
      <pubmed_id>7693088</pubmed_id>
    </reference>
  </general_references>
  <synthesis_reference/>
  <msds_url>http://hmdb.ca/system/metabolites/msds/000/009/915/original/HMDB11185.pdf?1358461243</msds_url>
  <enzymes>
    <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>
  </enzymes>
  <transporters>
    <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>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>Water + L-Threonine O-3-phosphate &gt; Phosphate + L-Threonine</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
