<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:12:05 UTC</creation_date>
  <update_date>2019-11-26 03:12:20 UTC</update_date>
  <accession>FDB015857</accession>
  <name>Gibberellin A23</name>
  <description>Gibberellin a23 is a member of the class of compounds known as c20-gibberellin 6-carboxylic acids. C20-gibberellin 6-carboxylic acids are c20-gibberellins with a carboxyl group at the 6-position. Gibberellin a23 is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Gibberellin a23 can be found in sweet potato, which makes gibberellin a23 a potential biomarker for the consumption of this food product.</description>
  <synonyms>
    <synonym>GA23</synonym>
    <synonym>Gibberellin A23</synonym>
    <synonym>Lupinus gibberellin II</synonym>
  </synonyms>
  <chemical_formula>C20H26O7</chemical_formula>
  <average_molecular_weight>378.4162</average_molecular_weight>
  <monisotopic_moleculate_weight>378.167853186</monisotopic_moleculate_weight>
  <iupac_name>8-formyl-5,12-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4-dicarboxylic acid</iupac_name>
  <traditional_iupac>8-formyl-5,12-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4-dicarboxylic acid</traditional_iupac>
  <cas_registry_number>20134-29-6</cas_registry_number>
  <smiles>CC1(C2C(C(O)=O)C34CC(=C)C(O)(C3)CCC4C2(CCC1O)C=O)C(O)=O</smiles>
  <inchi>InChI=1S/C20H26O7/c1-10-7-19-8-20(10,27)6-3-11(19)18(9-21)5-4-12(22)17(2,16(25)26)14(18)13(19)15(23)24/h9,11-14,22,27H,1,3-8H2,2H3,(H,23,24)(H,25,26)</inchi>
  <inchikey>HRIAGYDCQBIJJM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as c20-gibberellin 6-carboxylic acids. These are c20-gibberellins with a carboxyl group at the 6-position.</description>
    <direct_parent>C20-gibberellin 6-carboxylic acids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Diterpenoids</sub_class>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Aldehydes</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Gibberellane-6-carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.54e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 179-181°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.23</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>3.84</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-0.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>8-formyl-5,12-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4-dicarboxylic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>378.4162</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>378.167853186</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1(C2C(C(O)=O)C34CC(=C)C(O)(C3)CCC4C2(CCC1O)C=O)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C20H26O7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C20H26O7/c1-10-7-19-8-20(10,27)6-3-11(19)18(9-21)5-4-12(22)17(2,16(25)26)14(18)13(19)15(23)24/h9,11-14,22,27H,1,3-8H2,2H3,(H,23,24)(H,25,26)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>HRIAGYDCQBIJJM-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>132.13</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>92.84</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>38.02</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>90333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>90334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>90335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>153468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>153469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>153470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605868</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Sweet potato</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ipomoea batatas</name_scientific>
      <ncbi_taxonomy_id>4120</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
