<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:15 UTC</creation_date>
  <update_date>2019-11-26 03:07:10 UTC</update_date>
  <accession>FDB012599</accession>
  <name>3-(Methylseleno)alanine</name>
  <description>Se-Methylselenocysteine (SeMSC) is a naturally occurring seleno-amino acid that is synthesized by plants such as garlic, astragalus, onions and broccoli. Unlike selenomethionine, which is incorporated into proteins in place of methionine, SeMSC is not incorporated into any proteins, thereby being fully available for the synthesis of selenium-containing enzymes such as glutathione peroxidase. 3-(Methylseleno)alanine is found in many foods, some of which are common cabbage, white cabbage, lima bean, and cauliflower.</description>
  <synonyms>
    <synonym>(2R)-2-amino-3-methylselanylpropanoic acid</synonym>
    <synonym>(R)-2-Amino-3-(methylseleno)propionic acid</synonym>
    <synonym>3-(methylseleno)-L-Alanine</synonym>
    <synonym>3-(Methylseleno)alanine, 9CI</synonym>
    <synonym>C4H9NO2Se</synonym>
    <synonym>L-Alanine, 3-(methylseleno)-</synonym>
    <synonym>L-Methylselenocysteine</synonym>
    <synonym>L-se-methylselenocysteine</synonym>
    <synonym>Methyl-L-selenocysteine</synonym>
    <synonym>Methylselenocysteine</synonym>
    <synonym>Se-(methyl)selenocysteine hydrochloride</synonym>
    <synonym>Se-methyl-l-selenocysteine</synonym>
    <synonym>Se-methyl-seleno-l-cysteine</synonym>
    <synonym>Se-methyl-selenocysteine</synonym>
    <synonym>Se-Methylselenocysteine</synonym>
    <synonym>Selenium methyl cysteine</synonym>
    <synonym>Selenium-methylselenocystine</synonym>
    <synonym>Selenohomocysteine</synonym>
    <synonym>Selenomethylselenocysteine</synonym>
    <synonym>Selenomethylselenocysteine, (l)-isomer</synonym>
    <synonym>SEMC</synonym>
  </synonyms>
  <chemical_formula>C4H9NO2Se</chemical_formula>
  <average_molecular_weight>182.08</average_molecular_weight>
  <monisotopic_moleculate_weight>182.979850365</monisotopic_moleculate_weight>
  <iupac_name>2-amino-3-(methylselanyl)propanoic acid</iupac_name>
  <traditional_iupac>se-methylselenocysteine</traditional_iupac>
  <cas_registry_number>26046-90-2</cas_registry_number>
  <smiles>C[Se]CC(N)C(O)=O</smiles>
  <inchi>InChI=1S/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)</inchi>
  <inchikey>XDSSPSLGNGIIHP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <direct_parent>Alpha amino acids</direct_parent>
    <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>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <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>Selenoethers</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</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>Selenoether</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>non-proteinogenic alpha-amino acid</external_descriptor>
      <external_descriptor>selenocysteines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.56e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-3.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>1.46</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>8.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-amino-3-(methylselanyl)propanoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>182.08</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>182.979850365</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>C[Se]CC(N)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C4H9NO2Se</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>XDSSPSLGNGIIHP-UHFFFAOYSA-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>38.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>12.72</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</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>
  <pathways>
    <pathway>
      <name>Selenoamino Acid Metabolism</name>
      <smpdb_id>SMP00029</smpdb_id>
      <kegg_map_id>map00450</kegg_map_id>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>42497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>43404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>43405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>43406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>138807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>138808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>138809</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB04113</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>27812</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce31d3c4f8&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Cauliflower</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Brassica oleracea var. botrytis</name_scientific>
      <ncbi_taxonomy_id>3715</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common cabbage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Brassica oleracea</name_scientific>
      <ncbi_taxonomy_id>3712</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Garden onion</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Allium cepa</name_scientific>
      <ncbi_taxonomy_id>4679</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Garlic</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Allium sativum</name_scientific>
      <ncbi_taxonomy_id>4682</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Lima bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phaseolus lunatus</name_scientific>
      <ncbi_taxonomy_id>3884</ncbi_taxonomy_id>
    </food>
    <food>
      <name>White cabbage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Brassica oleracea L. var. capitata L. f. alba DC.</name_scientific>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Gamma-glutamyltransferase 5</name>
      <uniprot_id>P36269</uniprot_id>
      <uniprot_name/>
      <gene_name>GGT5</gene_name>
    </enzyme>
    <enzyme>
      <name>Gamma-glutamyltransferase 6</name>
      <uniprot_id>Q6P531</uniprot_id>
      <uniprot_name/>
      <gene_name>GGT6</gene_name>
    </enzyme>
    <enzyme>
      <name>Gamma-glutamyltransferase 7</name>
      <uniprot_id>Q9UJ14</uniprot_id>
      <uniprot_name/>
      <gene_name>GGT7</gene_name>
    </enzyme>
    <enzyme>
      <name>Gamma-glutamyltranspeptidase 1</name>
      <uniprot_id>P19440</uniprot_id>
      <uniprot_name/>
      <gene_name>GGT1</gene_name>
    </enzyme>
    <enzyme>
      <name>Kynurenine--oxoglutarate transaminase 1</name>
      <uniprot_id>Q16773</uniprot_id>
      <uniprot_name/>
      <gene_name>CCBL1</gene_name>
    </enzyme>
    <enzyme>
      <name>Kynurenine--oxoglutarate transaminase 3</name>
      <uniprot_id>Q6YP21</uniprot_id>
      <uniprot_name/>
      <gene_name>CCBL2</gene_name>
    </enzyme>
    <enzyme>
      <name>Selenocysteine lyase</name>
      <uniprot_id>Q96I15</uniprot_id>
      <uniprot_name/>
      <gene_name>SCLY</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Anti neoplastic</name>
      <id>465</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</definition>
    </health_effect>
  </health_effects>
</compound>
