<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-19 02:25:33 UTC</creation_date>
  <update_date>2026-08-20 01:14:19 UTC</update_date>
  <accession/>
  <common_name>(1R,2S,5R)-N-(4-METHOXYPHENYL)-5-METHYL-2-(1-METHYLETHYL)CYCLOHEXANECARBOXAMIDE</common_name>
  <class>SmallMolecule</class>
  <description>(1R,2S,5R)-N-(4-METHOXYPHENYL)-5-METHYL-2-(1-METHYLETHYL)CYCLOHEXANECARBOXAMIDE belongs to the monoterpenoids, a subclass of prenol lipids within the organic compounds. This compound has the chemical formula C18H27NO2 and an average molecular weight of 289.42 g/mol.

In industrial applications, the substance is used as a fragrance, as well as a flavouring and nutrient. It is recorded as being found in or released from eight different sources. These include electrical and electronic equipment, specifically microphones, electric hearing aids, auxiliary devices, and antennas. Additionally, it is found in household cleaning and consumer products, including tobacco product cases, pipe accessories, other smoking requisites, and tobacco product moisture control. Regarding its biological activity, it is a recorded activator of the protein target Transient receptor potential cation channel subfamily M member 8 (TRPM8).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C18H27NO2</chemical_formula>
  <average_molecular_weight>289.419</average_molecular_weight>
  <monisotopic_moleculate_weight>289.204179113</monisotopic_moleculate_weight>
  <iupac_name>(1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(propan-2-yl)cyclohexane-1-carboxamide</iupac_name>
  <traditional_iupac>(1R,2S,5R)-2-isopropyl-N-(4-methoxyphenyl)-5-methylcyclohexane-1-carboxamide</traditional_iupac>
  <cas_registry_number>68489-09-8</cas_registry_number>
  <smiles>[H][C@@]1(C)CC[C@@]([H])(C(C)C)[C@@]([H])(C1)C(=O)NC1=CC=C(OC)C=C1</smiles>
  <inchi>InChI=1S/C18H27NO2/c1-12(2)16-10-5-13(3)11-17(16)18(20)19-14-6-8-15(21-4)9-7-14/h6-9,12-13,16-17H,5,10-11H2,1-4H3,(H,19,20)/t13-,16+,17-/m1/s1</inchi>
  <inchikey>HNSGVPAAXJJOPQ-XOKHGSTOSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Monoterpenoids</sub_class>
    <direct_parent>Aromatic monoterpenoids</direct_parent>
    <alternate_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anilides</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Menthane monoterpenoids</alternative_parent>
      <alternative_parent>Methoxyanilines</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Monocyclic monoterpenoids</alternative_parent>
      <alternative_parent>N-arylamides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anilide</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aromatic monoterpenoid</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxyaniline</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Monocyclic monoterpenoid</substituent>
      <substituent>N-arylamide</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>P-menthane monoterpenoid</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>4.6</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.38e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(propan-2-yl)cyclohexane-1-carboxamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>289.419</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>289.204179113</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(C)CC[C@@]([H])(C(C)C)[C@@]([H])(C1)C(=O)NC1=CC=C(OC)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H27NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H27NO2/c1-12(2)16-10-5-13(3)11-17(16)18(20)19-14-6-8-15(21-4)9-7-14/h6-9,12-13,16-17H,5,10-11H2,1-4H3,(H,19,20)/t13-,16+,17-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HNSGVPAAXJJOPQ-XOKHGSTOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>38.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</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>
  </predicted_properties>
  <route_of_exposure/>
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  <metabolism/>
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  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7224599b18&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB19202</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>11266244</pubchem_compound_id>
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  <biocyc_id/>
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  <pdb_id/>
  <wikipidia/>
  <general_references/>
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</compound>
