<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:11:42 UTC</creation_date>
  <update_date>2025-11-19 00:53:13 UTC</update_date>
  <accession>FDB015200</accession>
  <name>Homocapsaicin</name>
  <description>Isolated from the pungent principle of red pepper (Capsicum annuum). Homocapsaicin is found in many foods, some of which are green bell pepper, pepper (c. annuum), herbs and spices, and italian sweet red pepper.</description>
  <synonyms>
    <synonym>9-Methyl-N-vanillyl-7-decenamide</synonym>
    <synonym>Homocapsaicin</synonym>
    <synonym>N-[(4-Hydroxy-3-methoxyphenyl)methyl]-9-methyl-7-decenamide, 9CI</synonym>
  </synonyms>
  <chemical_formula>C19H29NO3</chemical_formula>
  <average_molecular_weight>319.4385</average_molecular_weight>
  <monisotopic_moleculate_weight>319.214743799</monisotopic_moleculate_weight>
  <iupac_name>(7E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-9-methyldec-7-enamide</iupac_name>
  <traditional_iupac>homocapsaicin</traditional_iupac>
  <cas_registry_number>58493-48-4</cas_registry_number>
  <smiles>COC1=CC(CNC(=O)CCCCC\C=C\C(C)C)=CC=C1O</smiles>
  <inchi>InChI=1S/C19H29NO3/c1-15(2)9-7-5-4-6-8-10-19(22)20-14-16-11-12-17(21)18(13-16)23-3/h7,9,11-13,15,21H,4-6,8,10,14H2,1-3H3,(H,20,22)/b9-7+</inchi>
  <inchikey>JKIHLSTUOQHAFF-VQHVLOKHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.</description>
    <direct_parent>Methoxyphenols</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Methoxyphenols</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-amine</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>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.47e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 64.5-65.5°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>4.19</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.93</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-0.52</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(7E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-9-methyldec-7-enamide</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>319.4385</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>319.214743799</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=CC(CNC(=O)CCCCC\C=C\C(C)C)=CC=C1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C19H29NO3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C19H29NO3/c1-15(2)9-7-5-4-6-8-10-19(22)20-14-16-11-12-17(21)18(13-16)23-3/h7,9,11-13,15,21H,4-6,8,10,14H2,1-3H3,(H,20,22)/b9-7+</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>JKIHLSTUOQHAFF-VQHVLOKHSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>58.56</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>94.92</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>38.01</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>10</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>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>44817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>158313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>44424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>44425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>44426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>114642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>114643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>114644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2774072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2774073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2774074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2904309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2904310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2904311</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB36329</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:0x000055ce3066dc68&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Green bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
      <average_value>152.3</average_value>
      <max_value>300.0</max_value>
      <min_value>4.6</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Herbs and Spices</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Italian sweet red pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Orange bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
      <average_value>152.3</average_value>
      <max_value>300.0</max_value>
      <min_value>4.6</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
      <average_value>152.3</average_value>
      <max_value>300.0</max_value>
      <min_value>4.6</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Pepper (C. frutescens)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum var. annuum</name_scientific>
      <ncbi_taxonomy_id>40321</ncbi_taxonomy_id>
      <average_value>4.6</average_value>
      <max_value>4.6</max_value>
      <min_value>4.6</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Red bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
      <average_value>152.3</average_value>
      <max_value>300.0</max_value>
      <min_value>4.6</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Yellow bell pepper</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum</name_scientific>
      <ncbi_taxonomy_id>4072</ncbi_taxonomy_id>
      <average_value>152.3</average_value>
      <max_value>300.0</max_value>
      <min_value>4.6</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
