<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:25 UTC</creation_date>
  <update_date>2020-06-04 20:32:44 UTC</update_date>
  <accession>BMDB0000251</accession>
  <secondary_accessions>
    <accession>BMDB00251</accession>
  </secondary_accessions>
  <name>Taurine</name>
  <description>Taurine, also known as taufon or 2-sulfoethylamine, belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom). Taurine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Taurine exists in all living species, ranging from bacteria to humans. Taurine is a potentially toxic compound. Taurine has been found to be associated with several diseases known as perillyl alcohol administration for cancer treatment, schizophrenia, irritable bowel syndrome, and sulfite oxidase deficiency, isolated; also taurine has been linked to the inborn metabolic disorders including maple syrup urine disease.</description>
  <synonyms>
    <synonym>2-Aminoethanesulfonic acid</synonym>
    <synonym>2-Aminoethyl sulfonate</synonym>
    <synonym>Aminoethylsulfonic acid</synonym>
    <synonym>beta-Aminoethylsulfonic acid</synonym>
    <synonym>2-Aminoethanesulfonate</synonym>
    <synonym>2-Aminoethanesulphonate</synonym>
    <synonym>2-Aminoethanesulphonic acid</synonym>
    <synonym>2-Aminoethyl sulfonic acid</synonym>
    <synonym>2-Aminoethyl sulphonate</synonym>
    <synonym>2-Aminoethyl sulphonic acid</synonym>
    <synonym>Aminoethylsulfonate</synonym>
    <synonym>Aminoethylsulphonate</synonym>
    <synonym>Aminoethylsulphonic acid</synonym>
    <synonym>b-Aminoethylsulfonate</synonym>
    <synonym>b-Aminoethylsulfonic acid</synonym>
    <synonym>b-Aminoethylsulphonate</synonym>
    <synonym>b-Aminoethylsulphonic acid</synonym>
    <synonym>beta-Aminoethylsulfonate</synonym>
    <synonym>beta-Aminoethylsulphonate</synonym>
    <synonym>beta-Aminoethylsulphonic acid</synonym>
    <synonym>Β-aminoethylsulfonate</synonym>
    <synonym>Β-aminoethylsulfonic acid</synonym>
    <synonym>Β-aminoethylsulphonate</synonym>
    <synonym>Β-aminoethylsulphonic acid</synonym>
    <synonym>1-Aminoethane-2-sulfonate</synonym>
    <synonym>1-Aminoethane-2-sulfonic acid</synonym>
    <synonym>2-Aminoethylsulfonate</synonym>
    <synonym>2-Aminoethylsulfonic acid</synonym>
    <synonym>2-Sulfoethylamine</synonym>
    <synonym>Taurine hydrochloride</synonym>
    <synonym>Taurine zinc salt (2:1)</synonym>
    <synonym>Taurine, monopotassium salt</synonym>
    <synonym>Taufon</synonym>
    <synonym>Tauphon</synonym>
  </synonyms>
  <chemical_formula>C2H7NO3S</chemical_formula>
  <average_molecular_weight>125.147</average_molecular_weight>
  <monisotopic_moleculate_weight>125.014663785</monisotopic_moleculate_weight>
  <iupac_name>2-aminoethane-1-sulfonic acid</iupac_name>
  <traditional_iupac>taurine</traditional_iupac>
  <cas_registry_number>107-35-7</cas_registry_number>
  <smiles>NCCS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)</inchi>
  <inchikey>XOAAWQZATWQOTB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic sulfonic acids and derivatives</class>
    <sub_class>Organosulfonic acids and derivatives</sub_class>
    <direct_parent>Organosulfonic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkanesulfonic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Sulfonyls</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkanesulfonic acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Sulfonyl</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>amino sulfonic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>300 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>80.7 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-aminoethane-1-sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>125.147</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>125.014663785</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H7NO3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XOAAWQZATWQOTB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>24.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Taurine and Hypotaurine Metabolism</name>
      <smpdb_id>SMP0087214</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>166328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>166456</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>80 +/- 20</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>33-41</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>33-47</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Brain</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Epidermis</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Erythrocyte</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Fibroblasts</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Intestine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Kidney</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Leukocyte</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>2243 +/- 1186</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows</comment>
      <references>
        <reference>
          <reference_text>Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019.</reference_text>
          <pubmed_id>31867104</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus Thoracis Muscle</biospecimen>
      <concentration_value>480 +/- 146</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Mammary Gland</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform.</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951.</reference_text>
          <pubmed_id>31873721</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Mammary Gland</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform.</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951.</reference_text>
          <pubmed_id>31873721</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10 - 30</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>NRC. 1989. Recommended Dietary Allowances.  10th ed. Natl. Acad. Press, Washington, DC.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>327 - 621</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>37 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>41 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>38 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>37 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Neuron</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Pancreas</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Placenta</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Platelet</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Prostate Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Retina</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Ruminal Fluid</biospecimen>
      <concentration_value>8 +/- 7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Ruminal Fluid</biospecimen>
      <concentration_value>1.07 +/- 0.007</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Ruminal Fluid</biospecimen>
      <concentration_value>36.2 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus Muscle</biospecimen>
      <concentration_value>844 +/- 301</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>1510 +/- 296</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>1091</chemspider_id>
  <drugbank_id>DB01956</drugbank_id>
  <foodb_id>FDB003191</foodb_id>
  <kegg_id>C00245</kegg_id>
  <pdbe_id/>
  <chebi_id>15891</chebi_id>
  <pubchem_compound_id>1123</pubchem_compound_id>
  <meta_cyc_id>TAURINE</meta_cyc_id>
  <knapsack_id>C00048188</knapsack_id>
  <wikipedia_id>Taurine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34373</bigg_id>
  <metlin_id>31</metlin_id>
  <synthesis_reference>Hu, Libo; Zhu, Hui; Du, Da-Ming; Xu, Jiaxi. Efficient synthesis of taurine and structurally diverse substituted taurines from aziridines. Journal of Organic Chemistry  (2007),  72(12),  4543-4546.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>NRC. 1989. Recommended Dietary Allowances.  10th ed. Natl. Acad. Press, Washington, DC.</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00862</protein_accession>
      <name>Glutamate decarboxylase 1</name>
      <uniprot_id>Q0VCA1</uniprot_id>
      <gene_name>GAD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01376</protein_accession>
      <name>Acidic amino acid decarboxylase GADL1</name>
      <uniprot_id>A6QM00</uniprot_id>
      <gene_name>GADL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01848</protein_accession>
      <name>Glycine receptor subunit alpha-1</name>
      <uniprot_id>P57695</uniprot_id>
      <gene_name>GLRA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02539</protein_accession>
      <name>Sodium- and chloride-dependent taurine transporter</name>
      <uniprot_id>Q9MZ34</uniprot_id>
      <gene_name>SLC6A6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02851</protein_accession>
      <name>Glutathione hydrolase 6</name>
      <uniprot_id>A7YWM1</uniprot_id>
      <gene_name>GGT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
