<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 21:43:24 UTC</creation_date>
  <update_date>2026-05-14 17:19:55 UTC</update_date>
  <accession/>
  <common_name>Hyperforin</common_name>
  <class>SmallMolecule</class>
  <description>Hyperforin is a compound with the chemical formula C35H52O4. Hyperforin belongs to the monoterpenoids, a subclass of prenol lipids within the organic compounds. With an average molecular weight of 536.78 g/mol, Hyperforin is a heavy molecule.

This compound is found in or released from 15 recorded sources across several sectors. These include electrical and electronic equipment, specifically batteries, capacitors, printed circuit boards, wires and cables, and cell phones, as well as two additional sources in that category. It is present in healthcare, pharmaceuticals and veterinary products, including medical devices and antibiotics. In the textiles, leather and furnishings sector, it is found in synthetic textiles and carpets and rugs. Other recorded sources include food packaging within the food, food processing and cookware sector, and lubricants within both the industrial manufacturing and chemical processing sector and the energy, oil and gas sector, along with one more sector. Recorded exposure routes for the compound include oral, touch, and inhalation.

Hyperforin interacts with four recorded protein targets. It acts as an inhibitor of the nuclear receptor subfamily 1 group I member 2 (NR1I2). Additionally, its protein targets include glycogen phosphorylase, muscle form (PYGM), polyunsaturated fatty acid 5-lipoxygenase (ALOX5), and prostaglandin G/H synthase 1 (PTGS1).</description>
  <categories/>
  <types>
    <type>PFAS</type>
    <type>Phytotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C35H52O4</chemical_formula>
  <average_molecular_weight>536.785</average_molecular_weight>
  <monisotopic_moleculate_weight>536.386560152</monisotopic_moleculate_weight>
  <iupac_name>4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione</iupac_name>
  <traditional_iupac>4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione</traditional_iupac>
  <cas_registry_number>11079-53-1</cas_registry_number>
  <smiles>CC(C)C(=O)C12C(=O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC(CC=C(C)C)C1(C)CCC=C(C)C)C2=O</smiles>
  <inchi>InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3</inchi>
  <inchikey>KGSZHKRKHXOAMG-UHFFFAOYSA-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>Bicyclic monoterpenoids</direct_parent>
    <alternate_parents>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Enols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Bicyclic monoterpenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Enol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic 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>9.67</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.97e-04 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>9.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>536.785</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>536.386560152</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)C(=O)C12C(=O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC(CC=C(C)C)C1(C)CCC=C(C)C)C2=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C35H52O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KGSZHKRKHXOAMG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>71.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>166.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>63.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</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:0x00007f7275204ec0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01892</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>441298</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>16736597</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
    <target>
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      <target_id>BE0000017</target_id>
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      <target_id>BE0000248</target_id>
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  </targets>
</compound>
