<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:06:40 UTC</creation_date>
  <update_date>2025-11-19 02:40:35 UTC</update_date>
  <accession>FDB021993</accession>
  <name>3-(3-Hydroxyphenyl)propanoic acid</name>
  <description>3-(3-Hydroxyphenyl)propanoic (hMPP) acid is one of the major metabolites of ingested caffeic acid (PMID 15479001) and of the phenolic degradation products of proanthocyanidins (the most abundant polyphenol present in chocolate) by the microflora in the colon (PMID 12663291). mHPP is suspected to have antioxidants properties and is actively absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers (PMID 15479001, 12663291). [HMDB]</description>
  <synonyms>
    <synonym>3-(3-Hydroxy-phenyl)-propanoate</synonym>
    <synonym>3-(3-Hydroxy-phenyl)-propanoic acid</synonym>
    <synonym>3-(3-Hydroxy-phenyl)-propionic acid</synonym>
    <synonym>3-(3-Hydroxyphenyl)propanoate</synonym>
    <synonym>3-(3-Hydroxyphenyl)propanoic acid</synonym>
    <synonym>3-(3-Hydroxyphenyl)propionate</synonym>
    <synonym>3-(3-Hydroxyphenyl)propionic acid</synonym>
    <synonym>3-(m-Hydroxyphenyl)propionate</synonym>
    <synonym>3-(m-Hydroxyphenyl)propionic acid</synonym>
    <synonym>3-Hydroxybenzenepropanoate</synonym>
    <synonym>3-Hydroxybenzenepropanoic acid</synonym>
    <synonym>3-Hydroxydihydrocinnamate</synonym>
    <synonym>3-Hydroxydihydrocinnamic acid</synonym>
    <synonym>3-Hydroxyhydrocinnamic acid</synonym>
    <synonym>3-Hydroxyphenylpropanoate</synonym>
    <synonym>3-Hydroxyphenylpropanoic acid</synonym>
    <synonym>3-Hydroxyphenylpropionate</synonym>
    <synonym>3-Hydroxyphenylpropionic acid</synonym>
    <synonym>b-(3-Hydroxyphenyl)propionate</synonym>
    <synonym>b-(3-Hydroxyphenyl)propionic acid</synonym>
    <synonym>b-(m-Hydroxyphenyl)propionate</synonym>
    <synonym>b-(m-Hydroxyphenyl)propionic acid</synonym>
    <synonym>beta-(3-Hydroxyphenyl)propionate</synonym>
    <synonym>beta-(3-Hydroxyphenyl)propionic acid</synonym>
    <synonym>beta-(m-Hydroxyphenyl)propionate</synonym>
    <synonym>beta-(m-Hydroxyphenyl)propionic acid</synonym>
    <synonym>dihydro-3-Coumarate</synonym>
    <synonym>dihydro-3-Coumaric acid</synonym>
    <synonym>Dihydro-m-coumarate</synonym>
    <synonym>Dihydro-m-coumaric acid</synonym>
    <synonym>m-Hydrocoumaric acid</synonym>
    <synonym>m-hydroxy-Hydrocinnamate</synonym>
    <synonym>m-hydroxy-Hydrocinnamic acid</synonym>
    <synonym>m-Hydroxyphenylpropionate</synonym>
    <synonym>m-Hydroxyphenylpropionic acid</synonym>
    <synonym>β-(m-hydroxyphenyl)propionate</synonym>
    <synonym>β-(m-hydroxyphenyl)propionic acid</synonym>
  </synonyms>
  <chemical_formula>C9H10O3</chemical_formula>
  <average_molecular_weight>166.1739</average_molecular_weight>
  <monisotopic_moleculate_weight>166.062994186</monisotopic_moleculate_weight>
  <iupac_name>3-(3-hydroxyphenyl)propanoic acid</iupac_name>
  <traditional_iupac>3-hydroxyphenylpropionic acid</traditional_iupac>
  <cas_registry_number>621-54-5</cas_registry_number>
  <smiles>OC(=O)CCC1=CC=CC(O)=C1</smiles>
  <inchi>InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)</inchi>
  <inchikey>QVWAEZJXDYOKEH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.</description>
    <direct_parent>Phenylpropanoic acids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Phenylpropanoic acids</class>
    <sub_class/>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</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>
    </substituents>
    <external_descriptors>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.80e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>1.75</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>4.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>3-(3-hydroxyphenyl)propanoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>166.1739</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>166.062994186</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC(=O)CCC1=CC=CC(O)=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C9H10O3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>QVWAEZJXDYOKEH-UHFFFAOYSA-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>43.95</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>16.92</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</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>
    <pathway>
      <name>Metabolsim and Physiological Effects of 4-Ethylphenylsulfate</name>
      <smpdb_id>SMP0125541</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>462</spectrum_id>
    </spectrum>
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      <type>Specdb::CMs</type>
      <spectrum_id>5608</spectrum_id>
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      <type>Specdb::CMs</type>
      <spectrum_id>29889</spectrum_id>
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      <spectrum_id>155067</spectrum_id>
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      <type>Specdb::CMs</type>
      <spectrum_id>1059869</spectrum_id>
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      <type>Specdb::CMs</type>
      <spectrum_id>1059871</spectrum_id>
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      <type>Specdb::CMs</type>
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      <type>Specdb::CMs</type>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::MsMs</type>
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      <spectrum_id>2894728</spectrum_id>
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  </spectra>
  <hmdb_id>HMDB00375</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:0x000055ce31699308&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31699150&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31698f70&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31698d40&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
