<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 04:30:42 UTC</creation_date>
  <update_date>2026-05-14 17:22:54 UTC</update_date>
  <accession/>
  <common_name>Urocanic acid</common_name>
  <class>SmallMolecule</class>
  <description>Urocanic acid is an organic compound with the chemical formula C6H6N2O2 and an average molecular weight of 138.12 g/mol. Urocanic acid belongs to the imidazoles, a subclass of azoles within the organic compounds. In an industrial context, the compound is utilized as a UV stabilizer.

The substance is found in or released from five recorded sources. Within the category of food, food processing, and cookware, it is associated with the processing of meats, the processing of fish, and the preparation of vinegar. Additionally, it is found in electrical and electronic equipment, specifically in antennas and auxiliary devices. Regarding its biological activity, urocanic acid has one recorded protein target, which is urocanate hydratase (hutU).</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>Imidazoleacrylic acid</synonym>
  </synonyms>
  <chemical_formula>C6H6N2O2</chemical_formula>
  <average_molecular_weight>138.124</average_molecular_weight>
  <monisotopic_moleculate_weight>138.042927446</monisotopic_moleculate_weight>
  <iupac_name>(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid</iupac_name>
  <traditional_iupac>trans-urocanic acid</traditional_iupac>
  <cas_registry_number>104-98-3</cas_registry_number>
  <smiles>OC(=O)\C=C\C1=CNC=N1</smiles>
  <inchi>InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+</inchi>
  <inchikey>LOIYMIARKYCTBW-OWOJBTEDSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Azoles</class>
    <sub_class>Imidazoles</sub_class>
    <direct_parent>Imidazolyl carboxylic acids and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazolyl carboxylic acid 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>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>urocanic acid</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0000009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0000044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidinemia</name>
      <smpdb_id>SMP0000191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidinemia</name>
      <smpdb_id>SMP0125711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Keratinization</name>
      <smpdb_id>SMP0674009</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-1</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.25e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>138.124</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>138.042927446</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)\C=C\C1=CNC=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H6N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LOIYMIARKYCTBW-OWOJBTEDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>65.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</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>
  </predicted_properties>
  <route_of_exposure/>
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  <use_source/>
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  <symptoms/>
  <treatment/>
  <drugbank_id>DB01971</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>736715</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>643824</chemspider_id>
  <kegg_id/>
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  <chebi_id/>
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  <wikipidia/>
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</compound>
