<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:09:12 UTC</creation_date>
  <update_date>2019-11-26 03:03:51 UTC</update_date>
  <accession>FDB010583</accession>
  <name>Octopamine</name>
  <description>Octopamine, also known as beta,4-dihydroxyphenethylamine, is an endogenous biogenic amine that is closely related to norepinephrine, and has effects on the adrenergic and dopaminergic systems. Octopamine is found in lemon, sweet orange, and pepper (c. frutescens).</description>
  <synonyms>
    <synonym>(RS)-4-(2-amino-1-hydroxy-ethyl)phenol</synonym>
    <synonym>(RS)-octopamine</synonym>
    <synonym>1-(4-Hydroxyphenyl)-2-aminoethanol</synonym>
    <synonym>1-(p-hydroxyphenyl)-2-aminoethanol</synonym>
    <synonym>2-Amino-1-(4-hydroxyphenyl)ethanol</synonym>
    <synonym>4-(2R-amino-1-HYDROXYETHYL)phenol</synonym>
    <synonym>4-[2-amino-1-Hydroxyethyl]phenol</synonym>
    <synonym>4-Hydroxyphenethanolamine</synonym>
    <synonym>a-(Aminomethyl)-4-hydroxybenzenemethanol, 9CI</synonym>
    <synonym>a-(Aminomethyl)-p-hydroxybenzyl alcohol, 8CI</synonym>
    <synonym>Analet</synonym>
    <synonym>beta-Hydroxytyramine</synonym>
    <synonym>beta,4-dihydroxyphenethylamine</synonym>
    <synonym>DL-Octopamine</synonym>
    <synonym>ND 50</synonym>
    <synonym>Norden</synonym>
    <synonym>Noroxedrine</synonym>
    <synonym>Norphen</synonym>
    <synonym>Norsympathol</synonym>
    <synonym>Norsympatol</synonym>
    <synonym>Norsynephrine</synonym>
    <synonym>Norton</synonym>
    <synonym>p-(b-Amino-a-hydroxyethyl)phenol</synonym>
    <synonym>p-Hydroxyphenylethanolamine</synonym>
    <synonym>Racemic octopamine</synonym>
  </synonyms>
  <chemical_formula>C8H11NO2</chemical_formula>
  <average_molecular_weight>153.1784</average_molecular_weight>
  <monisotopic_moleculate_weight>153.078978601</monisotopic_moleculate_weight>
  <iupac_name>4-(2-amino-1-hydroxyethyl)phenol</iupac_name>
  <traditional_iupac>octopamine</traditional_iupac>
  <cas_registry_number>104-14-3</cas_registry_number>
  <smiles>NCC(O)C1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2</inchi>
  <inchikey>QHGUCRYDKWKLMG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.</description>
    <direct_parent>1-hydroxy-2-unsubstituted benzenoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>1-hydroxy-2-unsubstituted benzenoids</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</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>Secondary alcohol</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>phenylethanolamines</external_descriptor>
      <external_descriptor>tyramines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.72e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-0.32</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.64</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>8.98</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>4-(2-amino-1-hydroxyethyl)phenol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>153.1784</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>153.078978601</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>NCC(O)C1=CC=C(O)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C8H11NO2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>QHGUCRYDKWKLMG-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>66.48</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>42.47</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>16.16</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>1</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>1422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>78945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439768</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB04825</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>17134</chebi_id>
  <biocyc_id/>
  <het_id>OTR</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce2f743620&gt;</reference>
    <reference>#&lt;Reference:0x000055ce2f743008&gt;</reference>
  </general_references>
  <foods>
    <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>Mandarin orange (Clementine, Tangerine)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Citrus reticulata</name_scientific>
      <ncbi_taxonomy_id>85571</ncbi_taxonomy_id>
      <average_value>0.15</average_value>
      <max_value>0.15</max_value>
      <min_value>0.15</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Pepper (C. frutescens)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capsicum annuum var. annuum</name_scientific>
      <ncbi_taxonomy_id>40321</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sweet orange</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Citrus sinensis</name_scientific>
      <ncbi_taxonomy_id>2711</ncbi_taxonomy_id>
      <average_value>0.05</average_value>
      <max_value>0.05</max_value>
      <min_value>0.05</min_value>
      <unit>mg/100 g</unit>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Alpha-2A adrenergic receptor</name>
      <uniprot_id>P08913</uniprot_id>
      <uniprot_name/>
      <gene_name>ADRA2A</gene_name>
    </enzyme>
    <enzyme>
      <name>Alpha-2B adrenergic receptor</name>
      <uniprot_id>P18089</uniprot_id>
      <uniprot_name/>
      <gene_name>ADRA2B</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
