<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2015-06-04 19:10:39 -0600</creation_date>
  <update_date>2015-08-05 16:22:05 -0600</update_date>
  <accession>ECMDB23839</accession>
  <m2m_id>M2MDB004847</m2m_id>
  <name>3,4-Dihydroxy-L-phenylalanine</name>
  <description>An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease</description>
  <synonyms>
    <synonym>(-)-3-(3,4-Dihydroxyphenyl)-L-alanine</synonym>
    <synonym>(-)-Dopa</synonym>
    <synonym>(2S)-2-amino-3-(3,4-Dihydroxyphenyl)propanoate</synonym>
    <synonym>(2S)-2-amino-3-(3,4-Dihydroxyphenyl)propanoic acid</synonym>
    <synonym>3,4-Dihydroxy-L-phenylalanine</synonym>
    <synonym>3,4-Dihydroxyphenyl-L-alanine</synonym>
    <synonym>3,4-DIHYDROXYPHENYLALANINE</synonym>
    <synonym>3-(3,4-Dihydroxyphenyl)-L-alanine</synonym>
    <synonym>3-Hydroxy-L-tyrosine</synonym>
    <synonym>b-(3,4-Dihydroxyphenyl)-a-L-alanine</synonym>
    <synonym>b-(3,4-Dihydroxyphenyl)-L-alanine</synonym>
    <synonym>b-(3,4-Dihydroxyphenyl)alanine</synonym>
    <synonym>Bendopa</synonym>
    <synonym>beta-(3,4-Dihydroxyphenyl)-alpha-L-alanine</synonym>
    <synonym>beta-(3,4-Dihydroxyphenyl)-L-alanine</synonym>
    <synonym>beta-(3,4-Dihydroxyphenyl)alanine</synonym>
    <synonym>Cidandopa</synonym>
    <synonym>Dihydroxy-L-phenylalanine</synonym>
    <synonym>Dihydroxyphenylalanine</synonym>
    <synonym>Dopaflex</synonym>
    <synonym>Dopaidan</synonym>
    <synonym>Dopal</synonym>
    <synonym>Dopalina</synonym>
    <synonym>Dopar</synonym>
    <synonym>Doparkine</synonym>
    <synonym>Doparl</synonym>
    <synonym>Dopasol</synonym>
    <synonym>Dopaston</synonym>
    <synonym>Dopastone</synonym>
    <synonym>Dopastral</synonym>
    <synonym>Dopicar</synonym>
    <synonym>Doprin</synonym>
    <synonym>Eldopal</synonym>
    <synonym>Eldopar</synonym>
    <synonym>Eldopatec</synonym>
    <synonym>Eurodopa</synonym>
    <synonym>helfo-Dopa</synonym>
    <synonym>Insulamina</synonym>
    <synonym>L-(-)-Dopa</synonym>
    <synonym>L-3-(3,4-Dihydroxyphenyl)-alanine</synonym>
    <synonym>L-4-5-Dihydroxyphenylalanine</synonym>
    <synonym>L-b-(3,4-Dihydroxyphenyl)-a-alanine</synonym>
    <synonym>L-b-(3,4-Dihydroxyphenyl)alanine</synonym>
    <synonym>L-beta-(3,4-Dihydroxyphenyl)-alpha-alanine</synonym>
    <synonym>L-beta-(3,4-Dihydroxyphenyl)alanine</synonym>
    <synonym>L-Dihydroxyphenylalanine</synonym>
    <synonym>L-β-(3,4-Dihydroxyphenyl)-α-alanine</synonym>
    <synonym>L-β-(3,4-dihydroxyphenyl)alanine</synonym>
    <synonym>Laradopa</synonym>
    <synonym>Larodopa</synonym>
    <synonym>Ledopa</synonym>
    <synonym>Levedopa</synonym>
    <synonym>Levodopum</synonym>
    <synonym>Levopa</synonym>
    <synonym>Maipedopa</synonym>
    <synonym>Parda</synonym>
    <synonym>Pardopa</synonym>
    <synonym>Prodopa</synonym>
    <synonym>Syndopa</synonym>
    <synonym>Veldopa</synonym>
    <synonym>Weldopa</synonym>
    <synonym>β-(3,4-dihydroxyphenyl)-L-alanine</synonym>
    <synonym>β-(3,4-Dihydroxyphenyl)-α-L-alanine</synonym>
    <synonym>β-(3,4-dihydroxyphenyl)alanine</synonym>
  </synonyms>
  <chemical_formula>C9H11NO4</chemical_formula>
  <average_molecular_weight>197.1879</average_molecular_weight>
  <monisotopic_moleculate_weight>197.068807845</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid</iupac_name>
  <traditional_iupac>levodopa</traditional_iupac>
  <cas_registry_number>59-92-7</cas_registry_number>
  <smiles>N[C@@H](CC1=CC(O)=C(O)C=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1</inchi>
  <inchikey>WTDRDQBEARUVNC-LURJTMIESA-N</inchikey>
  <state/>
  <cellular_locations>
  </cellular_locations>
  <predicted_properties>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-1.8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>1.65</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>9.06</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>197.1879</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>197.068807845</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>N[C@@H](CC1=CC(O)=C(O)C=C1)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C9H11NO4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>WTDRDQBEARUVNC-LURJTMIESA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>103.78</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>49.08</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>18.91</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>4</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>
    <pathway>
      <name>Tyrosine metabolism</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00350</kegg_map_id>
      <subject/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>168678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1052801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1052803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1052804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1052806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1052808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1052810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1052812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1052814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1052815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1052817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1052819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1052821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1190</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id>C00355</kegg_id>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <foodb_id/>
  <general_references>
  </general_references>
  <synthesis_reference/>
  <msds_url/>
  <enzymes>
  </enzymes>
  <transporters>
  </transporters>
  <reactions>
    <reaction_text>3,4-Dihydroxy-L-phenylalanine + Oxygen &lt;&gt; 4-(L-Alanin-3-yl)-2-hydroxy-cis,cis-muconate 6-semialdehyde</reaction_text>
    <kegg_reaction_id>R02075 </kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
