<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:04:49 UTC</creation_date>
  <update_date>2019-11-26 02:55:52 UTC</update_date>
  <accession>FDB001066</accession>
  <name>Nonivamide</name>
  <description>Alkaloid from Capsicum subspecies Flavouring ingredient

Nonivamide is an organic compound and a capsaicinoid. It is an amide of pelargonic acid and vanillylamine. It is present in chili peppers, but is commonly manufactured synthetically. It is more heat-stable than capsaicin. Nonivamide is found in many foods, some of which are yellow bell pepper, pepper (c. frutescens), orange bell pepper, and herbs and spices.</description>
  <synonyms>
    <synonym>4-Hydroxy-3-methoxy-N-(1-oxononyl)-benzamide</synonym>
    <synonym>Benzamide, 4-hydroxy-3-methoxy-N-(1-oxononyl)-</synonym>
    <synonym>FEMA 2787</synonym>
    <synonym>HH 50</synonym>
    <synonym>Hydroxymethoxybenzyl pelargonamide</synonym>
    <synonym>N-((4-Hydroxy-3-methoxyphenyl)methyl)-nonanamide</synonym>
    <synonym>N-((4-Hydroxy-3-methoxyphenyl)methyl)nonanamide</synonym>
    <synonym>N-((Hydroxy-3-methoxyphenyl)methyl)4-nonanamide</synonym>
    <synonym>N-(4-Hydroxy-3-methoxybenzyl)nonanamide</synonym>
    <synonym>N-[(4-Hydroxy-3-methoxyphenyl)methyl]-nonanamide</synonym>
    <synonym>N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide, 9CI</synonym>
    <synonym>N-Nonanoyl vanillylamide</synonym>
    <synonym>N-Vanillyl nonanamide</synonym>
    <synonym>N-Vanillyl-nonanamide</synonym>
    <synonym>N-Vanillylnonamide</synonym>
    <synonym>N-Vanillylnonanamide, 8CI</synonym>
    <synonym>N-Vanillylpelargonamide</synonym>
    <synonym>Nonanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-</synonym>
    <synonym>Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-</synonym>
    <synonym>Nonanamide, N-vanillyl-</synonym>
    <synonym>Nonanoic acid vanillylamide</synonym>
    <synonym>Nonanoyl 4-hydroxy-3-methoxybenzylamide</synonym>
    <synonym>Nonanoyl vanillylamide</synonym>
    <synonym>Nonoyl vanillylamide</synonym>
    <synonym>Nonylic acid vanillylamide</synonym>
    <synonym>Nonylvanylamide</synonym>
    <synonym>Pelargonic acid vanillylamide</synonym>
    <synonym>Pelargonoyl vanillylamide</synonym>
    <synonym>Pelargonyl vanillylamide</synonym>
    <synonym>Pseudocapsaicin</synonym>
    <synonym>PSVA</synonym>
    <synonym>Synthetic capsaicin</synonym>
    <synonym>Vanillyl N-nonoylamide</synonym>
    <synonym>Vanillyl pelargonic amide</synonym>
    <synonym>Vanillyl-N-nonylamide</synonym>
  </synonyms>
  <chemical_formula>C17H27NO3</chemical_formula>
  <average_molecular_weight>293.4012</average_molecular_weight>
  <monisotopic_moleculate_weight>293.199093735</monisotopic_moleculate_weight>
  <iupac_name>N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide</iupac_name>
  <traditional_iupac>nonivamide</traditional_iupac>
  <cas_registry_number>2444-46-4</cas_registry_number>
  <smiles>CCCCCCCCC(=O)NCC1=CC(OC)=C(O)C=C1</smiles>
  <inchi>InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)</inchi>
  <inchikey>RGOVYLWUIBMPGK-UHFFFAOYSA-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>Carboximidic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</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>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</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>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>an alkaloid</external_descriptor>
      <external_descriptor>capsaicinoid</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.33e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.82</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>-1.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>293.4012</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>293.199093735</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CCCCCCCCC(=O)NCC1=CC(OC)=C(O)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C17H27NO3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>RGOVYLWUIBMPGK-UHFFFAOYSA-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>84.65</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>35.07</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::NmrOneD</type>
      <spectrum_id>3863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>41587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>100475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>166529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2235971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2237396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2238138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2239456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2240122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2241566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2242176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2243708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2250555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2251815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2255051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2423398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2423399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2423400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2515362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2515363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2515364</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB29846</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>46936</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce31f00668&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>2.35</average_value>
      <max_value>2.35</max_value>
      <min_value>2.35</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>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>2.35</average_value>
      <max_value>2.35</max_value>
      <min_value>2.35</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>2.35</average_value>
      <max_value>2.35</max_value>
      <min_value>2.35</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>2.35</average_value>
      <max_value>2.35</max_value>
      <min_value>2.35</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>2.35</average_value>
      <max_value>2.35</max_value>
      <min_value>2.35</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>2.35</average_value>
      <max_value>2.35</max_value>
      <min_value>2.35</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>bland</name>
    </flavor>
    <flavor>
      <name>odorless</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
