<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:35 UTC</creation_date>
  <update_date>2020-05-21 16:27:10 UTC</update_date>
  <accession>BMDB0001352</accession>
  <secondary_accessions>
    <accession>BMDB01352</accession>
  </secondary_accessions>
  <name>Hydroxypyruvic acid</name>
  <description>Hydroxypyruvic acid, also known as Hydroxypyruvic acid or OH-pyr, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Hydroxypyruvic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Hydroxypyruvic acid exists in all living organisms, ranging from bacteria to humans. Hydroxypyruvic acid and L-alanine can be biosynthesized from pyruvic acid and L-serine through its interaction with the enzyme serine--pyruvate aminotransferase. In cattle, hydroxypyruvic acid is involved in the metabolic pathway called the glycine and serine metabolism pathway.</description>
  <synonyms>
    <synonym>3-Hydroxypyruvate</synonym>
    <synonym>3-Hydroxypyruvic acid</synonym>
    <synonym>Hydroxypyruvate</synonym>
    <synonym>3-Hydroxy-2-oxopropanoate</synonym>
    <synonym>3-Hydroxy-2-oxopropanoic acid</synonym>
    <synonym>beta-Hydroxypyruvate</synonym>
    <synonym>OH-Pyr</synonym>
    <synonym>OH-Pyruvate</synonym>
    <synonym>2-Oxo-3-hydroxypropanoic acid</synonym>
    <synonym>2-Oxo-3-hydroxypropionic acid</synonym>
    <synonym>3-Hydroxy-2-oxopropionic acid</synonym>
    <synonym>Hydroxypyruvic acid</synonym>
    <synonym>beta-Hydroxypyruvic acid</synonym>
    <synonym>β-Hydroxypyruvic acid</synonym>
  </synonyms>
  <chemical_formula>C3H4O4</chemical_formula>
  <average_molecular_weight>104.0615</average_molecular_weight>
  <monisotopic_moleculate_weight>104.010958616</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxy-2-oxopropanoic acid</iupac_name>
  <traditional_iupac>hydroxypyruvic acid</traditional_iupac>
  <cas_registry_number>1113-60-6</cas_registry_number>
  <smiles>OCC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h4H,1H2,(H,6,7)</inchi>
  <inchikey>HHDDCCUIIUWNGJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Beta hydroxy acids and derivatives</sub_class>
    <direct_parent>Beta hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Keto acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>3-hydroxy monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxy-2-oxopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>104.0615</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>104.010958616</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H4O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h4H,1H2,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HHDDCCUIIUWNGJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>19.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.17</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>-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>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>130903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>138637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2245682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2724749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2724750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2724751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2957085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2957086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2957087</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>C00168</kegg_id>
  <foodb_id>FDB030913</foodb_id>
  <chemspider_id>939</chemspider_id>
  <drugbank_id>DB02951</drugbank_id>
  <pubchem_compound_id>964</pubchem_compound_id>
  <chebi_id>30841</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00007563</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34120</bigg_id>
  <wikipedia_id>Hydroxypyruvic_acid</wikipedia_id>
  <metlin_id>482</metlin_id>
  <meta_cyc_id>OH-PYR</meta_cyc_id>
  <synthesis_reference>Behal, Francis J.  Hydroxypyruvic acid formation in Aspergillus niger.    Archives of Biochemistry and Biophysics  (1960),  88  110-12.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01367</protein_accession>
      <name>Serine--pyruvate aminotransferase</name>
      <uniprot_id>A7MBF1</uniprot_id>
      <gene_name>AGXT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
