<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:11:47 UTC</creation_date>
  <update_date>2019-11-26 03:11:30 UTC</update_date>
  <accession>FDB015352</accession>
  <name>Geosmin</name>
  <description>Implicated in off-flavour of shellfish, freshwater fish, drinking water and some vegetables

Geosmin, which literally translates to "earth smell", is an organic compound with a distinct earthy flavour and aroma, and is responsible for the earthy taste of beets and a contributor to the strong scent that occurs in the air when rain falls after a dry spell of weather (petrichor) or when soil is disturbed. The human nose is extremely sensitive to geosmin and is able to detect it at concentrations as low as 5 parts per trillion. Geosmin is found in corn.</description>
  <synonyms>
    <synonym>1,10-Dimethyl-9-decalol</synonym>
    <synonym>11,12,13-Trinor-5-eudesmanol</synonym>
    <synonym>4,8a-Dimethyloctahydro-4a(2H)-naphthalenol</synonym>
    <synonym>4,8alpha-Dimethyl-octahydro-naphthalen-4alpha-ol</synonym>
    <synonym>Octahydro-4,8a-dimethyl-4a(2H)-naphthalenol, 9CI</synonym>
  </synonyms>
  <chemical_formula>C12H22O</chemical_formula>
  <average_molecular_weight>182.3025</average_molecular_weight>
  <monisotopic_moleculate_weight>182.167065326</monisotopic_moleculate_weight>
  <iupac_name>4,8a-dimethyl-decahydronaphthalen-4a-ol</iupac_name>
  <traditional_iupac>geosmin</traditional_iupac>
  <cas_registry_number>19700-21-1</cas_registry_number>
  <smiles>CC1CCCC2(C)CCCCC12O</smiles>
  <inchi>InChI=1S/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3</inchi>
  <inchikey>JLPUXFOGCDVKGO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).</description>
    <direct_parent>Tertiary alcohols</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>a sesquiterpenoid derivative</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.12e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.17</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-0.0047</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>4,8a-dimethyl-decahydronaphthalen-4a-ol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>182.3025</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>182.167065326</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1CCCC2(C)CCCCC12O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C12H22O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>JLPUXFOGCDVKGO-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>54.58</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>22.19</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</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>22883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>44885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>159472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2284171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2284172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2284173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3081756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3081757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3081758</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB36461</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>46702</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce31ed3078&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Common beet</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Beta vulgaris</name_scientific>
      <ncbi_taxonomy_id>161934</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>
      <average_value>300.0</average_value>
      <max_value>400.0</max_value>
      <min_value>200.0</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>beet</name>
    </flavor>
    <flavor>
      <name>earth</name>
    </flavor>
    <flavor>
      <name>earthy</name>
    </flavor>
    <flavor>
      <name>fresh</name>
    </flavor>
    <flavor>
      <name>musty</name>
    </flavor>
    <flavor>
      <name>soil</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
