<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 05:32:27 UTC</creation_date>
  <update_date>2026-05-14 19:38:02 UTC</update_date>
  <accession/>
  <common_name>Gamolenic acid</common_name>
  <class>SmallMolecule</class>
  <description>Gamolenic acid is an organic compound with the chemical formula C18H30O2 and an average molecular weight of 278.43 g/mol. Gamolenic acid belongs to the lineolic acids and derivatives, a subclass of fatty acyls within the organic compounds.

This substance is found in or released from 15 recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is associated with dermatological preparations. In the sector of food, food processing, and cookware, it is linked to the processing of fish and the preparation of vinegar, wort, wine, or sparkling wine. It is also found in household cleaning and consumer products, specifically tobacco product cases and non-electric simulated smoking devices. Additionally, it is present in electrical and electronic equipment, including antennas, auxiliary devices, colour television systems, line transmission systems, microphones, and three other sources. The recorded route of exposure for gamolenic acid is oral.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>Gamma linolenic acid</synonym>
  </synonyms>
  <chemical_formula>C18H30O2</chemical_formula>
  <average_molecular_weight>278.4296</average_molecular_weight>
  <monisotopic_moleculate_weight>278.224580204</monisotopic_moleculate_weight>
  <iupac_name>(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid</iupac_name>
  <traditional_iupac>gamma linolenic acid</traditional_iupac>
  <cas_registry_number>506-26-3</cas_registry_number>
  <smiles>CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O</smiles>
  <inchi>InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-</inchi>
  <inchikey>VZCCETWTMQHEPK-QNEBEIHSSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Lineolic acids and derivatives</sub_class>
    <direct_parent>Lineolic acids and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Octadecanoid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>Polyunsaturated fatty acids</descriptor>
      <descriptor>Unsaturated fatty acids</descriptor>
      <descriptor>Unsaturated fatty acids</descriptor>
      <descriptor>linolenic acid</descriptor>
      <descriptor>omega-6 fatty acid</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Alpha Linolenic Acid and Linoleic Acid Metabolism</name>
      <smpdb_id>SMP0000018</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>6.06</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.54e-04 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>278.4296</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>278.224580204</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H30O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VZCCETWTMQHEPK-QNEBEIHSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>89.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</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>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f726cf2f338&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB13854</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>5280933</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4444436</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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</compound>
