<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 22:43:04 UTC</creation_date>
  <update_date>2026-04-06 01:38:05 UTC</update_date>
  <accession/>
  <common_name>Artecanin</common_name>
  <class>SmallMolecule</class>
  <description>Artecanin is an organic compound with the chemical formula C15H18O5 and an average molecular weight of 278.30 g/mol. Artecanin belongs to the terpene lactones, a subclass of prenol lipids within the organic compounds.

This compound has been identified in or released from 27 recorded sources across multiple sectors. Within the electrical and electronic equipment sector, it is found in cell phones, capacitors, wires and cables, batteries, printed circuit boards, and 11 other sources. In the food, food processing and cookware sector, it is associated with food packaging, brew kettles, and the preparation of wort. It is also present in textiles, leather and furnishings, specifically in carpets, rugs, and synthetic textiles. Additionally, it is found in medical devices within the healthcare, pharmaceuticals and veterinary products sector, as well as in lubricants used in both energy, oil and gas, and industrial manufacturing and chemical processing. It has been recorded in three other sectors as well. Recorded exposure routes for artecanin include inhalation, oral, and touch.</description>
  <categories/>
  <types>
    <type>PFAS</type>
    <type>Phytotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C15H18O5</chemical_formula>
  <average_molecular_weight>278.3004</average_molecular_weight>
  <monisotopic_moleculate_weight>278.115423686</monisotopic_moleculate_weight>
  <iupac_name>(1R,2R,5S,9S,10S,11S,13R,14S)-2-hydroxy-2,11-dimethyl-6-methylidene-8,12,15-trioxapentacyclo[8.5.0.0¹,¹⁴.0⁵,⁹.0¹¹,¹³]pentadecan-7-one</iupac_name>
  <traditional_iupac>canin</traditional_iupac>
  <cas_registry_number>24959-84-0</cas_registry_number>
  <smiles>C[C@@]12O[C@@H]1[C@@H]1O[C@]11[C@H]2[C@H]2OC(=O)C(=C)[C@@H]2CC[C@@]1(C)O</smiles>
  <inchi>InChI=1S/C15H18O5/c1-6-7-4-5-13(2,17)15-9(8(7)18-12(6)16)14(3)10(19-14)11(15)20-15/h7-11,17H,1,4-5H2,2-3H3/t7-,8-,9-,10+,11-,13+,14-,15+/m0/s1</inchi>
  <inchikey>KXLUWEYBZBGJRZ-POEOZHCLSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Terpene lactones</sub_class>
    <direct_parent>Guaianolides and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>1,4-dioxepanes</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Enoate esters</alternative_parent>
      <alternative_parent>Epoxides</alternative_parent>
      <alternative_parent>Gamma butyrolactones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Sesquiterpenoids</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1,4-dioxepane</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Alpha,beta-unsaturated carboxylic ester</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Dioxepane</substituent>
      <substituent>Enoate ester</substituent>
      <substituent>Ether</substituent>
      <substituent>Gamma butyrolactone</substituent>
      <substituent>Guaianolide-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Oxirane</substituent>
      <substituent>Sesquiterpenoid</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>Guaianolide</descriptor>
      <descriptor>sesquiterpene lactone</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.92e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1R,2R,5S,9S,10S,11S,13R,14S)-2-hydroxy-2,11-dimethyl-6-methylidene-8,12,15-trioxapentacyclo[8.5.0.0¹,¹⁴.0⁵,⁹.0¹¹,¹³]pentadecan-7-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>278.3004</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>278.115423686</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@]12O[C@@H]1[C@@H]1O[C@]11[C@H]2[C@H]2OC(=O)C(=C)[C@@H]2CC[C@@]1(C)O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H18O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H18O5/c1-6-7-4-5-13(2,17)15-9(8(7)18-12(6)16)14(3)10(19-14)11(15)20-15/h7-11,17H,1,4-5H2,2-3H3/t7-,8-,9-,10+,11-,13+,14-,15+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KXLUWEYBZBGJRZ-POEOZHCLSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>71.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>66.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>27.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</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/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7226275520&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id/>
  <hmdb_id/>
  <pubchem_compound_id>442175</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>390688</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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  </targets>
</compound>
