<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 05:43:55 UTC</creation_date>
  <update_date>2026-05-14 18:19:09 UTC</update_date>
  <accession/>
  <common_name>Droxidopa</common_name>
  <class>SmallMolecule</class>
  <description>Droxidopa is an organic compound with the chemical formula C9H11NO5 and an average molecular weight of 213.19 g/mol. Droxidopa belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. 

This compound is identified in six recorded sources, including healthcare, pharmaceuticals and veterinary products specifically as cardiac stimulants excluding cardiac glycosides, as well as electrical and electronic equipment such as antennas, and building and construction materials including ceilings, fencing, ladders, stairs and ramps. The recorded route of exposure for this substance is oral.

In terms of biological activity, there are 10 recorded protein targets for droxidopa. It acts as an agonist or inhibitor of phenylalanine-4-hydroxylase (PAH) as well as the alpha-1A adrenergic receptor (ADRA1A), alpha-1B adrenergic receptor (ADRA1B), and alpha-1D adrenergic receptor (ADRA1D), among 6 other proteins.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C9H11NO5</chemical_formula>
  <average_molecular_weight>213.189</average_molecular_weight>
  <monisotopic_moleculate_weight>213.063722458</monisotopic_moleculate_weight>
  <iupac_name>(2S,3S)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid</iupac_name>
  <traditional_iupac>(2S,3S)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid</traditional_iupac>
  <cas_registry_number>23651-95-8</cas_registry_number>
  <smiles>[H][C@@](N)(C(O)=O)[C@@]([H])(O)C1=CC(O)=C(O)C=C1</smiles>
  <inchi>InChI=1S/C9H11NO5/c10-7(9(14)15)8(13)4-1-2-5(11)6(12)3-4/h1-3,7-8,11-13H,10H2,(H,14,15)/t7-,8-/m0/s1</inchi>
  <inchikey>QXWYKJLNLSIPIN-YUMQZZPRSA-N</inchikey>
  <taxonomy>
    <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>
    <direct_parent>Tyrosine and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Catechols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalanine and derivatives</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Catechol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tyrosine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-2.7</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.53e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3S)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>213.189</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>213.063722458</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](N)(C(O)=O)[C@@]([H])(O)C1=CC(O)=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11NO5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11NO5/c10-7(9(14)15)8(13)4-1-2-5(11)6(12)3-4/h1-3,7-8,11-13H,10H2,(H,14,15)/t7-,8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QXWYKJLNLSIPIN-YUMQZZPRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>124.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</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>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7221b29388&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB06262</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>6999030</pubchem_compound_id>
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  <chemspider_id/>
  <kegg_id/>
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  <chebi_id/>
  <biocyc_id/>
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  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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