<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 23:01:33 UTC</creation_date>
  <update_date>2020-05-21 16:26:59 UTC</update_date>
  <accession>BMDB0002757</accession>
  <secondary_accessions>
    <accession>BMDB02757</accession>
  </secondary_accessions>
  <name>Cysteic acid</name>
  <description>Cysteic acid, also known as cysteic acid or Cysteic acid, 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). Cysteic acid is possibly soluble (in water) and a very strong basic compound (based on its pKa). Cysteic acid exists in all living species, ranging from bacteria to humans. Cysteic acid participates in a number of enzymatic reactions, within cattle. In particular, Cysteic acid can be converted into taurine through the action of the enzyme cysteine sulfinic acid decarboxylase. In addition, Cysteic acid can be converted into taurine; which is catalyzed by the enzyme glutamate decarboxylase 1. In cattle, cysteic acid is involved in the metabolic pathway called the taurine and hypotaurine metabolism pathway.</description>
  <synonyms>
    <synonym>3-Sulfoalanine</synonym>
    <synonym>beta-Sulfoalanine</synonym>
    <synonym>Cysteine sulfonic acid</synonym>
    <synonym>3-Sulphoalanine</synonym>
    <synonym>b-Sulfoalanine</synonym>
    <synonym>b-Sulphoalanine</synonym>
    <synonym>beta-Sulphoalanine</synonym>
    <synonym>Β-sulfoalanine</synonym>
    <synonym>Β-sulphoalanine</synonym>
    <synonym>Cysteine sulfonate</synonym>
    <synonym>Cysteine sulphonate</synonym>
    <synonym>Cysteine sulphonic acid</synonym>
    <synonym>Cysteate</synonym>
    <synonym>2-Amino-3-sulfopropanoate</synonym>
    <synonym>2-Amino-3-sulfopropanoic acid</synonym>
    <synonym>2-Amino-3-sulfopropionate</synonym>
    <synonym>2-Amino-3-sulfopropionic acid</synonym>
    <synonym>Cepteate</synonym>
    <synonym>Cepteic acid</synonym>
    <synonym>Cipteate</synonym>
    <synonym>Cipteic acid</synonym>
    <synonym>Cysteinate</synonym>
    <synonym>Cysteinesulfonate</synonym>
    <synonym>Cysteinesulfonic acid</synonym>
    <synonym>Cysteinic acid</synonym>
    <synonym>Cysterate</synonym>
    <synonym>Cysteric acid</synonym>
    <synonym>L-Cysteate</synonym>
    <synonym>L-Cysteic acid</synonym>
    <synonym>3 Sulfoalanine</synonym>
    <synonym>Acid, cysteic</synonym>
    <synonym>beta Sulfoalanine</synonym>
  </synonyms>
  <chemical_formula>C3H7NO5S</chemical_formula>
  <average_molecular_weight>169.156</average_molecular_weight>
  <monisotopic_moleculate_weight>169.004493029</monisotopic_moleculate_weight>
  <iupac_name>2-amino-3-sulfopropanoic acid</iupac_name>
  <traditional_iupac>cysteic acid</traditional_iupac>
  <cas_registry_number>498-40-8</cas_registry_number>
  <smiles>NC(CS(O)(=O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)</inchi>
  <inchikey>XVOYSCVBGLVSOL-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>
    <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>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkanesulfonic acids</alternative_parent>
      <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>Organosulfonic acids</alternative_parent>
      <alternative_parent>Sulfonyls</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkanesulfonic acid</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>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid</substituent>
      <substituent>Organosulfonic acid or derivatives</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>alanine derivative</external_descriptor>
      <external_descriptor>amino sulfonic acid</external_descriptor>
      <external_descriptor>carboxyalkanesulfonic acid</external_descriptor>
      <external_descriptor>cysteine derivative</external_descriptor>
      <external_descriptor>non-proteinogenic alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-3-sulfopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>169.156</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>169.004493029</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CS(O)(=O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7NO5S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XVOYSCVBGLVSOL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>117.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</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>Taurine and Hypotaurine Metabolism</name>
      <smpdb_id>SMP0087214</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2227320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2227414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2229721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2229744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2232037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2232174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2234354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2234571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2238310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2239290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2244603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2245528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2246718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2247554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2248715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2249682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>130695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>138429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128944</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>128957</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</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>Liver</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>
  </normal_concentrations>
  <kegg_id>C00506</kegg_id>
  <foodb_id>FDB023061</foodb_id>
  <drugbank_id/>
  <chemspider_id>23942</chemspider_id>
  <pubchem_compound_id>25701</pubchem_compound_id>
  <chebi_id>21260</chebi_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <wikipedia_id>Cysteic_acid</wikipedia_id>
  <knapsack_id/>
  <bigg_id>35186</bigg_id>
  <metlin_id>332</metlin_id>
  <synthesis_reference>Zhao, Chong-tao; Wang, Qing-ping; Lin, Wan-zhen; Chen, Ping.  Synthesis of L-cysteic acid by indirect electrooxidation.    Jingxi Huagong  (2003),  20(4),  237-238, 253.</synthesis_reference>
  <general_references>
  </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_associations>
</metabolite>
