<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:26 UTC</creation_date>
  <update_date>2020-02-24 19:10:33 UTC</update_date>
  <accession>FDB002592</accession>
  <name>cis-p-Coumaric acid</name>
  <description>Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. cis-p-Coumaric acid is found in coriander.</description>
  <synonyms>
    <synonym>(2Z)-3-(4-Hydroxyphenyl)acrylate</synonym>
    <synonym>(2Z)-3-(4-Hydroxyphenyl)acrylic acid</synonym>
    <synonym>(Z)-3-(4-Hydroxyphenyl)-2-propenoate</synonym>
    <synonym>(Z)-3-(4-Hydroxyphenyl)-2-propenoic acid</synonym>
    <synonym>(Z)-P-Coumarate</synonym>
    <synonym>(Z)-P-Coumaric acid</synonym>
    <synonym>(Z)-P-Hydroxycinnamate</synonym>
    <synonym>(Z)-P-Hydroxycinnamic acid</synonym>
    <synonym>cis-4-Hydroxycinnamate</synonym>
    <synonym>cis-4-Hydroxycinnamic acid</synonym>
    <synonym>cis-p-coumarate</synonym>
    <synonym>cis-p-Coumaric acid</synonym>
    <synonym>cis-P-Coumarinate</synonym>
    <synonym>cis-P-Coumarinic acid</synonym>
    <synonym>cis-P-Hydroxycinnamate</synonym>
    <synonym>cis-P-Hydroxycinnamic acid</synonym>
  </synonyms>
  <chemical_formula>C9H8O3</chemical_formula>
  <average_molecular_weight>164.158</average_molecular_weight>
  <monisotopic_moleculate_weight>164.047344122</monisotopic_moleculate_weight>
  <iupac_name>(2Z)-3-(4-hydroxyphenyl)prop-2-enoic acid</iupac_name>
  <traditional_iupac>cis-p-coumaric acid</traditional_iupac>
  <cas_registry_number>4501-31-9</cas_registry_number>
  <smiles>OC(=O)\C=C/C1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3-</inchi>
  <inchikey>NGSWKAQJJWESNS-UTCJRWHESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.</description>
    <direct_parent>Hydroxycinnamic acids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Cinnamic acids and derivatives</class>
    <sub_class>Hydroxycinnamic acids and derivatives</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cinnamic acids</alternative_parent>
      <alternative_parent>Coumaric acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cinnamic acid</substituent>
      <substituent>Coumaric acid</substituent>
      <substituent>Coumaric acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxycinnamic acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Styrene</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>4-coumaric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.02e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 134-134.5 dec. (subl. from 124°)</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>1.83</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>3.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2Z)-3-(4-hydroxyphenyl)prop-2-enoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>164.158</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>164.047344122</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC(=O)\C=C/C1=CC=C(O)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C9H8O3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3-</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>NGSWKAQJJWESNS-UTCJRWHESA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>57.53</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>45.04</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>16.28</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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>3956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>3957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>3958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2418400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2418401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2418402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2543504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2543505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2543506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>42079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>167778</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB30677</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce32764660&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Coriander</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Coriandrum sativum</name_scientific>
      <ncbi_taxonomy_id>4047</ncbi_taxonomy_id>
      <average_value>85.65</average_value>
      <max_value>144.0</max_value>
      <min_value>27.3</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Grape wine</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
      <average_value>0.0</average_value>
      <max_value>0.0</max_value>
      <min_value>0.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Pear</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Pyrus communis</name_scientific>
      <ncbi_taxonomy_id>23211</ncbi_taxonomy_id>
      <average_value>3.2175</average_value>
      <max_value>18.275</max_value>
      <min_value>0.0</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
