<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 05:26:50 UTC</creation_date>
  <update_date>2026-04-03 01:46:10 UTC</update_date>
  <accession/>
  <common_name>Limoni</common_name>
  <class>SmallMolecule</class>
  <description>Limoni is an organic compound with the chemical formula C26H30O8 and an average molecular weight of 470.52 g/mol. Limoni belongs to the triterpenoids, a subclass of prenol lipids within the organic compounds.

This substance has been identified in or released from 11 recorded sources across several diverse categories. Within electrical and electronic equipment, it is associated with magnets, television systems, discharge lamps, and line transmission systems. In the context of food, food processing and cookware, it is linked to the preparation of malt, vinegar, and wine or sparkling wine. Additionally, limoni is found in household cleaning and consumer products, specifically regarding pipe accessories, other smoking requisites, and non-electric simulated smoking devices. It has also been recorded in building and construction materials, specifically ladders.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>Limonin</synonym>
    <synonym>Linonin</synonym>
  </synonyms>
  <chemical_formula>C26H30O8</chemical_formula>
  <average_molecular_weight>470.518</average_molecular_weight>
  <monisotopic_moleculate_weight>470.194067926</monisotopic_moleculate_weight>
  <iupac_name>(1R,2R,7S,10R,13R,14R,16S,19R,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione</iupac_name>
  <traditional_iupac>limonin</traditional_iupac>
  <cas_registry_number>1180-71-8</cas_registry_number>
  <smiles>CC1(C)O[C@H]2CC(=O)OC[C@@]22[C@H]1CC(=O)[C@]1(C)[C@@H]2CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)C1=COC=C1</smiles>
  <inchi>InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1</inchi>
  <inchikey>KBDSLGBFQAGHBE-MSGMIQHVSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Triterpenoids</sub_class>
    <direct_parent>Limonoids</direct_parent>
    <alternate_parents>
      <alternative_parent>1,4-dioxepanes</alternative_parent>
      <alternative_parent>11-oxosteroids</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Delta valerolactones</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Epoxides</alternative_parent>
      <alternative_parent>Furans</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Naphthalenes</alternative_parent>
      <alternative_parent>Naphthopyrans</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Steroid lactones</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1,4-dioxepane</substituent>
      <substituent>11-oxosteroid</substituent>
      <substituent>2-oxosteroid</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Delta valerolactone</substituent>
      <substituent>Delta_valerolactone</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Dioxepane</substituent>
      <substituent>Ether</substituent>
      <substituent>Furan</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Lactone</substituent>
      <substituent>Limonoid skeleton</substituent>
      <substituent>Naphthalene</substituent>
      <substituent>Naphthopyran</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>Oxosteroid</substituent>
      <substituent>Pyran</substituent>
      <substituent>Steroid</substituent>
      <substituent>Steroid lactone</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>Limonoids</descriptor>
      <descriptor>epoxide</descriptor>
      <descriptor>furans</descriptor>
      <descriptor>hexacyclic triterpenoid</descriptor>
      <descriptor>lactone</descriptor>
      <descriptor>limonoid</descriptor>
      <descriptor>organic heterohexacyclic compound</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>3.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.99e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>17.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1R,2R,7S,10R,13R,14R,16S,19R,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>470.518</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>470.194067926</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1(C)O[C@H]2CC(=O)OC[C@@]22[C@H]1CC(=O)[C@]1(C)[C@@H]2CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)C1=COC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H30O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KBDSLGBFQAGHBE-MSGMIQHVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>104.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>114.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</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:0x00007f72673f00a8&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id/>
  <hmdb_id/>
  <pubchem_compound_id>179651</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>156367</chemspider_id>
  <kegg_id/>
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  <chebi_id/>
  <biocyc_id/>
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  <wikipidia/>
  <general_references/>
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  </targets>
</compound>
