<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:00 UTC</creation_date>
  <update_date>2025-11-18 23:34:09 UTC</update_date>
  <accession>FDB012131</accession>
  <name>gamma-Sitosterol</name>
  <description>Clionasterol is a triterpenoid isolated from the Indian marine red alga Gracilaria edulis, the sponge Veronica aerophoba and the Kenyan Marine Green; Macroalga Halimeda macroloba. It is a potent inhibitor of complement component C1. (PMID 12624828). gamma-Sitosterol is found in many foods, some of which are rice, lemon, arabica coffee, and soy bean.</description>
  <synonyms>
    <synonym>(24alphaFH)-stigmast-5-en-3beta-ol</synonym>
    <synonym>(3beta,8xi,9xi,10xi,13xi,14xi,17xi,24S)-stigmast-5-en-3-ol</synonym>
    <synonym>&amp;beta;-dihydrofucosterol</synonym>
    <synonym>22,23-Dihydroporiferasterol</synonym>
    <synonym>24&amp;beta;-Ethyl-5-cholesten-3&amp;beta;-ol</synonym>
    <synonym>24&amp;beta;-Ethylcholesterol</synonym>
    <synonym>24b-Ethylcholest-5-en-3b-ol</synonym>
    <synonym>24b-Ethylcholesterol</synonym>
    <synonym>24S-Ethylcholest-5-en-3&amp;beta;-ol</synonym>
    <synonym>24S-Ethylcholest-5-en-3b-ol</synonym>
    <synonym>Azuprostat</synonym>
    <synonym>b-Dihydroeucosterol</synonym>
    <synonym>B-dihydrofucosterol</synonym>
    <synonym>Beta-dihydrofucosterol</synonym>
    <synonym>Clionasterol</synonym>
    <synonym>Fucosterol, &amp;beta;-dihydro-</synonym>
    <synonym>g-Sitosterol</synonym>
    <synonym>Gamma-sitosterol</synonym>
    <synonym>Poriferast-5-en-3b-ol</synonym>
    <synonym>Stigmast-5-en-3-ol</synonym>
    <synonym>Stigmast-5-en-3-ol, (3&amp;beta;,24S)-</synonym>
    <synonym>Stigmast-5-en-3&amp;beta;-ol, (24S)-</synonym>
  </synonyms>
  <chemical_formula>C29H50O</chemical_formula>
  <average_molecular_weight>414.7067</average_molecular_weight>
  <monisotopic_moleculate_weight>414.386166222</monisotopic_moleculate_weight>
  <iupac_name>14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol</iupac_name>
  <traditional_iupac>14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol</traditional_iupac>
  <cas_registry_number>83-47-6</cas_registry_number>
  <smiles>CCC(CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C</smiles>
  <inchi>InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3</inchi>
  <inchikey>KZJWDPNRJALLNS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.</description>
    <direct_parent>Stigmastanes and derivatives</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Stigmastanes and derivatives</sub_class>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>3-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>C24-propyl sterols and derivatives</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Triterpenoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>C24-propyl-sterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Stigmastane-skeleton</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>a triterpenoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.84e-05 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 147-148°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>7.84</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>18.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-1.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>414.7067</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>414.386166222</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CCC(CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C29H50O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>KZJWDPNRJALLNS-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>20.23</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>129.77</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>53.73</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>1</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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>93151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>120256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>120558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>125748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>129973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>79476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>79477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>79478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>140094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>140095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>140096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3402031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3402032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3402033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3402751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3402752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3402753</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB00649</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:0x000055ce332d7330&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Arabica coffee</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Coffea arabica</name_scientific>
      <ncbi_taxonomy_id>13443</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Coriander</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Coriandrum sativum</name_scientific>
      <ncbi_taxonomy_id>4047</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Corn</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zea mays</name_scientific>
      <ncbi_taxonomy_id>4577</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Dill</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anethum graveolens</name_scientific>
      <ncbi_taxonomy_id>40922</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Lemon</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Citrus limon</name_scientific>
      <ncbi_taxonomy_id>2708</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rice</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryza sativa</name_scientific>
      <ncbi_taxonomy_id>4530</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Soy bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Glycine max</name_scientific>
      <ncbi_taxonomy_id>3847</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Anti-oxidant</name>
      <id>502</id>
      <definition>A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.</definition>
    </health_effect>
  </health_effects>
</compound>
