<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 23:03:28 UTC</creation_date>
  <update_date>2020-05-21 16:26:51 UTC</update_date>
  <accession>BMDB0003288</accession>
  <secondary_accessions>
    <accession>BMDB03288</accession>
  </secondary_accessions>
  <name>Selenocysteine</name>
  <description>Selenocysteine, also known as Selenocysteine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Selenocysteine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Selenocysteine exists in all living species, ranging from bacteria to humans. Selenocysteine participates in a number of enzymatic reactions, within cattle. In particular, Selenocysteine can be converted into L-alanine and hydrogen selenide; which is mediated by the enzyme selenocysteine lyase. In addition, Selenocysteine and 2-ketobutyric acid can be biosynthesized from selenocystathionine; which is mediated by the enzyme cystathionine gamma-lyase. In cattle, selenocysteine is involved in the metabolic pathway called the selenoamino acid metabolism pathway.</description>
  <synonyms>
    <synonym>3-Selenyl-L-alanine</synonym>
    <synonym>L-Selenocystein</synonym>
    <synonym>L-Selenozystein</synonym>
    <synonym>(2R)-2-Amino-3-selanylpropanoate</synonym>
    <synonym>(2R)-2-Amino-3-selanylpropanoic acid</synonym>
    <synonym>3-Seleno-alanine</synonym>
    <synonym>3-Selenoalanine</synonym>
    <synonym>L-Selenocysteine</synonym>
  </synonyms>
  <chemical_formula>C3H7NO2Se</chemical_formula>
  <average_molecular_weight>168.05</average_molecular_weight>
  <monisotopic_moleculate_weight>168.964200301</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-amino-3-selanylpropanoic acid</iupac_name>
  <traditional_iupac>L-selenocysteine</traditional_iupac>
  <cas_registry_number>3614-08-2</cas_registry_number>
  <smiles>N[C@@H](C[SeH])C(O)=O</smiles>
  <inchi>InChI=1S/C3H7NO2Se/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1</inchi>
  <inchikey>ZKZBPNGNEQAJSX-REOHCLBHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Selenols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organoselenium compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Selenol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-alanine derivative</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
      <external_descriptor>selenocysteine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-amino-3-selanylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>168.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>168.964200301</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](C[SeH])C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7NO2Se</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7NO2Se/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZKZBPNGNEQAJSX-REOHCLBHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>33.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.67</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>3</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>Selenoamino Acid Metabolism</name>
      <smpdb_id>SMP0087161</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>153066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35882</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2717892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2717893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2717894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2963673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2963674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2963675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135569</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <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>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>Testis</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>Thyroid Gland</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>
  </normal_concentrations>
  <drugbank_id>DB02345</drugbank_id>
  <foodb_id>FDB002262</foodb_id>
  <chemspider_id>23436</chemspider_id>
  <kegg_id>C05688</kegg_id>
  <pubchem_compound_id>25076</pubchem_compound_id>
  <chebi_id>16633</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00034230</knapsack_id>
  <meta_cyc_id>L-SELENOCYSTEINE</meta_cyc_id>
  <wikipedia_id>Selenocysteine</wikipedia_id>
  <bigg_id>46290</bigg_id>
  <metlin_id>3292</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00391</protein_accession>
      <name>Ethanolaminephosphotransferase 1</name>
      <uniprot_id>Q17QM4</uniprot_id>
      <gene_name>SELENOI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00501</protein_accession>
      <name>Thioredoxin reductase 2, mitochondrial</name>
      <uniprot_id>Q9N2I8</uniprot_id>
      <gene_name>TXNRD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00539</protein_accession>
      <name>Selenocysteine lyase</name>
      <uniprot_id>A2VDS1</uniprot_id>
      <gene_name>SCLY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00540</protein_accession>
      <name>Thioredoxin reductase 1, cytoplasmic</name>
      <uniprot_id>O62768</uniprot_id>
      <gene_name>TXNRD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00541</protein_accession>
      <name>Phospholipid hydroperoxide glutathione peroxidase</name>
      <uniprot_id>Q9N2J2</uniprot_id>
      <gene_name>GPX4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00542</protein_accession>
      <name>Glutathione peroxidase 3</name>
      <uniprot_id>P37141</uniprot_id>
      <gene_name>GPX3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00543</protein_accession>
      <name>Iodothyronine deiodinase</name>
      <uniprot_id>Q5I3B0</uniprot_id>
      <gene_name>DIO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00544</protein_accession>
      <name>Glutathione peroxidase 1</name>
      <uniprot_id>P00435</uniprot_id>
      <gene_name>GPX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00545</protein_accession>
      <name>Iodothyronine deiodinase</name>
      <uniprot_id>Q9BDR5</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00546</protein_accession>
      <name>Type II iodothyronine deiodinase</name>
      <uniprot_id>Q5I3B2</uniprot_id>
      <gene_name>DIO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00547</protein_accession>
      <name>Methionine-R-sulfoxide reductase B1</name>
      <uniprot_id>Q3MHL9</uniprot_id>
      <gene_name>MSRB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00548</protein_accession>
      <name>Thyroxine 5-deiodinase</name>
      <uniprot_id>Q5I3B1</uniprot_id>
      <gene_name>DIO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00818</protein_accession>
      <name>Cystathionine gamma-lyase</name>
      <uniprot_id>Q58DW2</uniprot_id>
      <gene_name>CTH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01619</protein_accession>
      <name>Thioredoxin reductase-like selenoprotein T</name>
      <uniprot_id>A6QP01</uniprot_id>
      <gene_name>SELENOT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01620</protein_accession>
      <name>Selenoprotein S</name>
      <uniprot_id>Q2KI76</uniprot_id>
      <gene_name>SELENOS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01621</protein_accession>
      <name>Selenoprotein P</name>
      <uniprot_id>P49907</uniprot_id>
      <gene_name>SELENOP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01622</protein_accession>
      <name>Selenoprotein K</name>
      <uniprot_id>Q32PE3</uniprot_id>
      <gene_name>SELENOK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01623</protein_accession>
      <name>Selenoprotein F</name>
      <uniprot_id>A8YXY3</uniprot_id>
      <gene_name>SELENOF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
