<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2009-07-23 18:26:11 UTC</creation_date>
  <update_date>2026-04-05 15:21:40 UTC</update_date>
  <accession>T3D3089</accession>
  <common_name>Tutin</common_name>
  <class>SmallMolecule</class>
  <description>Tutin is an exogenous organic compound with the formula C15H18O6 and an average molecular weight of 294.30 g/mol. It exists as a solid at room temperature. Tutin belongs to the gamma butyrolactones, a subclass of lactones within the organic compounds.

The compound is a potent antagonist of the glycine receptor, with four recorded protein targets: glycine receptor subunit alpha-1 (GLRA1), glycine receptor subunit alpha-2 (GLRA2), glycine receptor subunit alpha-3 (GLRA3), and glycine receptor subunit beta (GLRB).

Tutin is found in or released from 30 recorded sources across various categories. In the realm of electrical and electronic equipment, it is associated with antennas, coils, adjustable resistors, auxiliary devices, cores yokes or armatures, and 12 other sources. Within building and construction, it is linked to tents or canopies, ladders, fencing, stairs and ramps, and roofs. It is also found in household items such as badges, and in household cleaning and consumer products including soap dispensers, cigar cigarettes, tobacco product moisture control, pipe accessories, and other smoking requisites. Additionally, it is found in food, food processing and cookware, specifically in the processing of meats and fish.</description>
  <categories>
    <category>Plant Toxin</category>
    <category>Natural Toxin</category>
  </categories>
  <types>
    <type>Organic Compound</type>
    <type>Ether</type>
    <type>Ester</type>
    <type>Plant Toxin</type>
    <type>Natural Compound</type>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms>
    <synonym>Toot poison</synonym>
    <synonym>Tutine</synonym>
    <synonym>TUTU</synonym>
  </synonyms>
  <chemical_formula>C15H18O6</chemical_formula>
  <average_molecular_weight>294.2998</average_molecular_weight>
  <monisotopic_moleculate_weight>294.110338308</monisotopic_moleculate_weight>
  <iupac_name>2',8'-dihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-11'-one</iupac_name>
  <traditional_iupac>2',8'-dihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-11'-one</traditional_iupac>
  <cas_registry_number>2571-22-4</cas_registry_number>
  <smiles>CC(=C)C1C2OC(=O)C1C1(O)C3OC3C3(CO3)C1(C)C2O</smiles>
  <inchi>InChI=1S/C15H18O6/c1-5(2)6-7-12(17)20-8(6)9(16)13(3)14(4-19-14)10-11(21-10)15(7,13)18/h6-11,16,18H,1,4H2,2-3H3</inchi>
  <inchikey>CCAZWUJBLXKBAY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Lactones</class>
    <sub_class>Gamma butyrolactones</sub_class>
    <direct_parent>Gamma butyrolactones</direct_parent>
    <alternate_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Epoxides</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>Oxepanes</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Gamma butyrolactone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Oxepane</substituent>
      <substituent>Oxirane</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin>Exogenous</origin>
  <cellular_locations>
    <cellular_location>Cytoplasm</cellular_location>
    <cellular_location>Extracellular</cellular_location>
  </cellular_locations>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state>Solid</state>
  <appearance>White powder.</appearance>
  <experimental_properties>
    <property>
      <kind>solubility</kind>
      <value>19 mg/mL at 10°C [BEILSTEIN]</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.87e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2',8'-dihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-11'-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>294.2998</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>294.110338308</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=C)C1C2OC(=O)C1C1(O)C3OC3C3(CO3)C1(C)C2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H18O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H18O6/c1-5(2)6-7-12(17)20-8(6)9(16)13(3)14(4-19-14)10-11(21-10)15(7,13)18/h6-11,16,18H,1,4H2,2-3H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CCAZWUJBLXKBAY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>91.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>67.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.23</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>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>
  </predicted_properties>
  <route_of_exposure>Oral (ingestion) (L1817) ; dermal (L1817)</route_of_exposure>
  <mechanism_of_toxicity>Tutin is a potent antagonist of the glycine receptor. (L1250)</mechanism_of_toxicity>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use_source>Tutin is a plant toxin found in the tutu plant (genus Coriaria). (L1250)</use_source>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7221b1ddf8&gt;</health_effects>
  <symptoms>Tutin has powerful convulsant effects. (L1250)</symptoms>
  <treatment/>
  <drugbank_id/>
  <hmdb_id/>
  <pubchem_compound_id>75729</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id/>
  <kegg_id>C09570</kegg_id>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id>Tutin </stitch_id>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references>
    <reference>
      <reference_text>Wikipedia. Tutin. Last Updated 23 May 2009. : http://en.wikipedia.org/wiki/Tutin</reference_text>
    </reference>
    <reference>
      <reference_text>Wikipedia. Phytotoxin. Last Updated 7 August 2009.: http://en.wikipedia.org/wiki/Phytotoxin</reference_text>
    </reference>
  </general_references>
  <targets>
    <target>
      <target_id/>
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      <constants/>
      <references/>
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      <references/>
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    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000433</target_id>
      <mechanism_of_action>Tutin is a potent antagonist of the glycine receptor. (L1250)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Tutin. Last Updated 23 May 2009. : http://en.wikipedia.org/wiki/Tutin</reference_text>
        </reference>
      </references>
    </target>
    <target>
      <target_id>BE0000745</target_id>
      <mechanism_of_action>Tutin is a potent antagonist of the glycine receptor. (L1250)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Tutin. Last Updated 23 May 2009. : http://en.wikipedia.org/wiki/Tutin</reference_text>
        </reference>
      </references>
    </target>
    <target>
      <target_id>BE0000414</target_id>
      <mechanism_of_action>Tutin is a potent antagonist of the glycine receptor. (L1250)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Tutin. Last Updated 23 May 2009. : http://en.wikipedia.org/wiki/Tutin</reference_text>
        </reference>
      </references>
    </target>
    <target>
      <target_id>BE0005329</target_id>
      <mechanism_of_action>Tutin is a potent antagonist of the glycine receptor. (L1250)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Tutin. Last Updated 23 May 2009. : http://en.wikipedia.org/wiki/Tutin</reference_text>
        </reference>
      </references>
    </target>
    <target>
      <target_id>BE0000055</target_id>
      <mechanism_of_action>Tutin is a potent antagonist of the glycine receptor. (L1250)</mechanism_of_action>
      <constants/>
      <references>
        <reference>
          <reference_text>Wikipedia. Tutin. Last Updated 23 May 2009. : http://en.wikipedia.org/wiki/Tutin</reference_text>
        </reference>
      </references>
    </target>
  </targets>
</compound>
