<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:09 UTC</creation_date>
  <update_date>2025-11-18 23:36:16 UTC</update_date>
  <accession>FDB012399</accession>
  <name>Gyrocyanin</name>
  <description>Constituent of the mushroom Gyroporus cyanescens (cornflower bolete). Gyrocyanin is found in mushrooms.</description>
  <synonyms>
    <synonym>3,5-Bis(4-hydroxyphenyl)-1,2,4-cyclopentanetrione</synonym>
    <synonym>4-Hydroxy-2,5-bis(4-hydroxyphenyl)-4-cyclopentene-1,3-dione, 9CI</synonym>
  </synonyms>
  <chemical_formula>C17H12O5</chemical_formula>
  <average_molecular_weight>296.2742</average_molecular_weight>
  <monisotopic_moleculate_weight>296.068473494</monisotopic_moleculate_weight>
  <iupac_name>4-hydroxy-2,5-bis(4-hydroxyphenyl)cyclopent-4-ene-1,3-dione</iupac_name>
  <traditional_iupac>4-hydroxy-2,5-bis(4-hydroxyphenyl)cyclopent-4-ene-1,3-dione</traditional_iupac>
  <cas_registry_number>52591-12-5</cas_registry_number>
  <smiles>OC1=C(C(=O)C(C1=O)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C17H12O5/c18-11-5-1-9(2-6-11)13-15(20)14(17(22)16(13)21)10-3-7-12(19)8-4-10/h1-8,13,18-19,22H</inchi>
  <inchikey>DIFAFZFNMSLGGN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.</description>
    <direct_parent>1-hydroxy-2-unsubstituted benzenoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>1-hydroxy-2-unsubstituted benzenoids</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Beta-diketones</alternative_parent>
      <alternative_parent>Cyclic ketones</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>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>1,3-diketone</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Enol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.71e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 240° (darkens)</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.95</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>7.53</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>4-hydroxy-2,5-bis(4-hydroxyphenyl)cyclopent-4-ene-1,3-dione</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>296.2742</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>296.068473494</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC1=C(C(=O)C(C1=O)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C17H12O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C17H12O5/c18-11-5-1-9(2-6-11)13-15(20)14(17(22)16(13)21)10-3-7-12(19)8-4-10/h1-8,13,18-19,22H</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>DIFAFZFNMSLGGN-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>94.83</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>80.46</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>29.65</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>3</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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>43725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>146835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>91200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>91201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>91202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>154539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>154540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>154541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2812973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2812974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2812975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2896137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2896138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2896139</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB34126</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce316b1778&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Common mushroom</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Agaricus bisporus</name_scientific>
      <ncbi_taxonomy_id>5341</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mushrooms</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Oyster mushroom</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Pleurotus ostreatus</name_scientific>
      <ncbi_taxonomy_id>5322</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
