<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:07:34 UTC</creation_date>
  <update_date>2025-11-18 23:04:43 UTC</update_date>
  <accession>FDB007359</accession>
  <name>Gentianine</name>
  <description>Gentianine, also known as 4-(2-hydroxyethyl)-5-vinylnicotinate g-lactone, is a member of the class of compounds known as pyranopyridines. Pyranopyridines are polycyclic aromatic compounds containing a pyran ring fused to a pyridine ring. Gentianine is soluble (in water) and a strong basic compound (based on its pKa). Gentianine is a bitter tasting compound found in fenugreek, which makes gentianine a potential biomarker for the consumption of this food product.</description>
  <synonyms>
    <synonym>4-(2-hydroxyethyl)-5-vinylnicotinic acid gamma-lactone</synonym>
    <synonym>5-ethenyl-3,4-dihydro-1H-pyrano[3,4-c]pyridin-1-one</synonym>
    <synonym>From schultesia guianensis malme (mata-zombando)</synonym>
    <synonym>Gencianina</synonym>
    <synonym>Gentianine</synonym>
  </synonyms>
  <chemical_formula>C10H9NO2</chemical_formula>
  <average_molecular_weight>175.184</average_molecular_weight>
  <monisotopic_moleculate_weight>175.063328537</monisotopic_moleculate_weight>
  <iupac_name>5-ethenyl-1H,3H,4H-pyrano[3,4-c]pyridin-1-one</iupac_name>
  <traditional_iupac>gentianine</traditional_iupac>
  <cas_registry_number>439-89-4</cas_registry_number>
  <smiles>C=CC1=C2CCOC(=O)C2=CN=C1</smiles>
  <inchi>InChI=1S/C10H9NO2/c1-2-7-5-11-6-9-8(7)3-4-13-10(9)12/h2,5-6H,1,3-4H2</inchi>
  <inchikey>DFNZYFAJQPLJFI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyranopyridines. These are polycyclic aromatic compounds containing a pyran ring fused to a pyridine ring.</description>
    <direct_parent>Pyranopyridines</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyranopyridines</class>
    <sub_class/>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pyridinecarboxylic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pyranopyridine</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridine carboxylic acid</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>lactone</external_descriptor>
      <external_descriptor>pyranopyridine</external_descriptor>
      <external_descriptor>pyridine alkaloid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.94e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>1.34</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>3.01</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>5-ethenyl-1H,3H,4H-pyrano[3,4-c]pyridin-1-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>175.184</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>175.063328537</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>C=CC1=C2CCOC(=O)C2=CN=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H9NO2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H9NO2/c1-2-7-5-11-6-9-8(7)3-4-13-10(9)12/h2,5-6H,1,3-4H2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>DFNZYFAJQPLJFI-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>39.19</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>48.92</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>17.61</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>0</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>5658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>86151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>86152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>86153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>148404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>148405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>148406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603958</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>28981</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Fenugreek</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Trigonella foenum-graecum</name_scientific>
      <ncbi_taxonomy_id>78534</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>bitter</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Analgesic</name>
      <id>56</id>
      <definition>An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.</definition>
    </health_effect>
    <health_effect>
      <name>Anti bacterial</name>
      <id>145</id>
      <definition>A substance that kills or slows the growth of bacteria.</definition>
    </health_effect>
    <health_effect>
      <name>Anti histaminic</name>
      <id>331</id>
      <definition>Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.</definition>
    </health_effect>
    <health_effect>
      <name>Anti psychotic</name>
      <id>564</id>
      <definition>Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-anaphylactic</name>
      <id>111</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-arthritic</name>
      <id>131</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-edemic</name>
      <id>248</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti-inflammatory</name>
      <id>370</id>
      <definition>A substance that reduces or suppresses inflammation.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-meningitic</name>
      <id>428</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-rheumatic</name>
      <id>585</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-shigellic</name>
      <id>610</id>
      <definition>A substance that kills or slows the growth of bacteria.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-staphylococcic</name>
      <id>627</id>
      <definition>A substance that kills or slows the growth of bacteria.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-streptococcic</name>
      <id>631</id>
      <definition>A substance that kills or slows the growth of bacteria.</definition>
    </health_effect>
    <health_effect>
      <name>Ataractic</name>
      <id>713</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Central nervous system paralytic</name>
      <id>814</id>
      <definition>A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.</definition>
    </health_effect>
    <health_effect>
      <name>Central nervous system stimulant</name>
      <id>816</id>
      <definition>A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.</definition>
    </health_effect>
    <health_effect>
      <name>Corticosterogenic</name>
      <id>837</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Emetic</name>
      <id>899</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Hypoglycemic</name>
      <id>1017</id>
      <definition>A drug which lowers the blood glucose level.</definition>
    </health_effect>
    <health_effect>
      <name>Hypotensive</name>
      <id>1021</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Myorelaxant</name>
      <id>1134</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Neurotoxic</name>
      <id>1160</id>
      <definition>A poison that interferes with the functions of the nervous system.</definition>
    </health_effect>
    <health_effect>
      <name>Pesticide</name>
      <id>1210</id>
      <definition>Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.</definition>
    </health_effect>
    <health_effect>
      <name>Sedative</name>
      <id>1311</id>
      <definition>A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.</definition>
    </health_effect>
  </health_effects>
</compound>
