<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2020-04-17 18:38:16 UTC</creation_date>
  <update_date>2020-12-07 19:10:58 UTC</update_date>
  <accession>CDB004802</accession>
  <secondary_accessions>
  </secondary_accessions>
  <name>gamma-Aminobutyric acid</name>
  <description>gamma-Aminobutyric acid, also known as GABA or g-amino-butanoate, belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. gamma-Aminobutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. gamma-Aminobutyric acid exists in all living species, ranging from bacteria to humans. Outside of the human body, gamma-Aminobutyric acid has been detected, but not quantified in, several different foods, such as fox grapes, oxheart cabbages, garden onion (var.), yellow zucchinis, and chinese mustards. This could make gamma-aminobutyric acid a potential biomarker for the consumption of these foods. gamma-Aminobutyric acid is a potentially toxic compound. A gamma-amino acid that is butanoic acid with the amino substituent located at C-4. gamma-Aminobutyric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.</description>
  <synonyms>
    <synonym>4-Aminobutanoic acid</synonym>
    <synonym>4-Aminobutyric acid</synonym>
    <synonym>4Abu</synonym>
    <synonym>GABA</synonym>
    <synonym>GAMMA-AMINO-butanoIC ACID</synonym>
    <synonym>gamma-Amino-N-butyric acid</synonym>
    <synonym>gamma-Aminobutanoic acid</synonym>
    <synonym>gamma-Aminobuttersaeure</synonym>
    <synonym>Omega-aminobutyric acid</synonym>
    <synonym>Piperidic acid</synonym>
    <synonym>Piperidinic acid</synonym>
    <synonym>4-Aminobutyrate</synonym>
    <synonym>Gammalon</synonym>
    <synonym>4-Aminobutanoate</synonym>
    <synonym>g-AMINO-butanoate</synonym>
    <synonym>g-AMINO-butanoic acid</synonym>
    <synonym>gamma-AMINO-butanoate</synonym>
    <synonym>Γ-amino-butanoate</synonym>
    <synonym>Γ-amino-butanoic acid</synonym>
    <synonym>g-Amino-N-butyrate</synonym>
    <synonym>g-Amino-N-butyric acid</synonym>
    <synonym>gamma-Amino-N-butyrate</synonym>
    <synonym>Γ-amino-N-butyrate</synonym>
    <synonym>Γ-amino-N-butyric acid</synonym>
    <synonym>g-Aminobutanoate</synonym>
    <synonym>g-Aminobutanoic acid</synonym>
    <synonym>gamma-Aminobutanoate</synonym>
    <synonym>Γ-aminobutanoate</synonym>
    <synonym>Γ-aminobutanoic acid</synonym>
    <synonym>g-Aminobuttersaeure</synonym>
    <synonym>Γ-aminobuttersaeure</synonym>
    <synonym>Omega-aminobutyrate</synonym>
    <synonym>Piperidate</synonym>
    <synonym>Piperidinate</synonym>
    <synonym>g-Aminobutyrate</synonym>
    <synonym>g-Aminobutyric acid</synonym>
    <synonym>gamma-Aminobutyrate</synonym>
    <synonym>Γ-aminobutyrate</synonym>
    <synonym>Γ-aminobutyric acid</synonym>
    <synonym>3-Carboxypropylamine</synonym>
    <synonym>Aminalon</synonym>
    <synonym>Gaballon</synonym>
    <synonym>Gamarex</synonym>
    <synonym>gamma Aminobutyrate</synonym>
    <synonym>gamma Aminobutyric acid</synonym>
    <synonym>Gammalone</synonym>
    <synonym>Gammar</synonym>
    <synonym>Gammasol</synonym>
    <synonym>Mielogen</synonym>
    <synonym>Mielomade</synonym>
    <synonym>W-Aminobutyrate</synonym>
    <synonym>W-Aminobutyric acid</synonym>
    <synonym>gamma-Aminobutyric acid, calcium salt (2:1)</synonym>
    <synonym>gamma-Aminobutyric acid, hydrochloride</synonym>
    <synonym>gamma-Aminobutyric acid, zinc salt (2:1)</synonym>
    <synonym>4 Aminobutanoic acid</synonym>
    <synonym>4 Aminobutyric acid</synonym>
    <synonym>Lithium gaba</synonym>
    <synonym>gamma Aminobutyric acid, monolithium salt</synonym>
    <synonym>gamma Aminobutyric acid, monosodium salt</synonym>
    <synonym>gamma-Aminobutyric acid, monolithium salt</synonym>
    <synonym>gamma-Aminobutyric acid, monosodium salt</synonym>
    <synonym>Acid, hydrochloride gamma-aminobutyric</synonym>
    <synonym>Aminalone</synonym>
    <synonym>GABA, lithium</synonym>
    <synonym>Hydrochloride gamma-aminobutyric acid</synonym>
    <synonym>gamma Aminobutyric acid, hydrochloride</synonym>
    <synonym>4-Amino-butanoate</synonym>
    <synonym>gamma-Aminobutyric acid</synonym>
  </synonyms>
  <chemical_formula>C4H9NO2</chemical_formula>
  <average_molecular_weight>103.12</average_molecular_weight>
  <monisotopic_molecular_weight>103.0633</monisotopic_molecular_weight>
  <iupac_name>4-aminobutanoic acid</iupac_name>
  <traditional_iupac>gamma(amino)-butyric acid</traditional_iupac>
  <cas_registry_number>56-12-2</cas_registry_number>
  <smiles>NCCCC(O)=O</smiles>
  <inchi>InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)</inchi>
  <inchikey>BTCSSZJGUNDROE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.</description>
    <direct_parent>Gamma amino acids and derivatives</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Gamma amino acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</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>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>gamma-amino acid</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <property>
      <kind>water_solubility</kind>
      <value>1300.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.17</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
    <property>
      <kind>melting_point</kind>
      <value>203 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-aminobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>103.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>103.0633</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H9NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BTCSSZJGUNDROE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</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>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <kegg_id>C00334</kegg_id>
  <drugbank_id>DB02530</drugbank_id>
  <foodb_id>FDB030489</foodb_id>
  <chemspider_id>116</chemspider_id>
  <pubchem_compound_id>119</pubchem_compound_id>
  <pdb_id/>
  <chebi_id>16865</chebi_id>
  <knapsack_id>C00001337</knapsack_id>
  <biocyc_id>4-AMINO-BUTYRATE</biocyc_id>
  <wikipedia_id>Gamma-Aminobutyric_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34652</bigg_id>
  <metlin_id/>
  <general_references>
  </general_references>
</compound>

