<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:22:57 UTC</creation_date>
  <update_date>2025-11-19 02:42:59 UTC</update_date>
  <accession>FDB022992</accession>
  <name>N-Methyl-D-aspartic acid</name>
  <description>N-Methyl-D-aspartic acid is an amino acid derivative acting as a specific agonist at the NMDA receptor, and therefore mimics the action of the neurotransmitter glutamate on that receptor. In contrast to glutamate, NMDA binds to and regulates the above receptor only, but not other glutamate receptors. 
NMDA is a water-soluble synthetic substance that is not normally found in biological tissue. It was first synthesized in the 1960's. NMDA is an excitotoxin; this trait has applications in behavioral neuroscience research. The body of work utilizing this technique falls under the term "lesion studies." Researchers apply NMDA to specific regions of an (animal) subject's brain or spinal cord and subsequently test for the behavior of interest, such as operant behavior. If the behavior is compromised, it suggests the destroyed tissue was part of a brain region that made an important contribution to the normal expression of that behavior.
Examples of antagonists of the NMDA receptor are APV, dextromethorphan, ketamine, phencyclidine (PCP), riluzole, and memantine. They are commonly referred to as NMDA receptor antagonists.  [HMDB]</description>
  <synonyms>
    <synonym>(R)-2-Methylamino-succinate</synonym>
    <synonym>(R)-2-Methylamino-succinic acid</synonym>
    <synonym>2-Methylamino-succinate</synonym>
    <synonym>2-Methylamino-succinic acid</synonym>
    <synonym>Methyl aspartate</synonym>
    <synonym>Methyl aspartic acid</synonym>
    <synonym>N-Me-D-Asp-OH</synonym>
    <synonym>N-Methyl aspartate</synonym>
    <synonym>N-Methyl aspartic acid</synonym>
    <synonym>N-methyl D-aspartate</synonym>
    <synonym>N-methyl D-aspartic acid</synonym>
    <synonym>N-Methyl-D-aspartate</synonym>
    <synonym>N-Methylaspartate</synonym>
    <synonym>N-Methylaspartic acid</synonym>
    <synonym>NMDA</synonym>
  </synonyms>
  <chemical_formula>C5H9NO4</chemical_formula>
  <average_molecular_weight>147.1293</average_molecular_weight>
  <monisotopic_moleculate_weight>147.053157781</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-(methylamino)butanedioic acid</iupac_name>
  <traditional_iupac>N methyl D aspartate</traditional_iupac>
  <cas_registry_number>6384-92-5</cas_registry_number>
  <smiles>CN[C@H](CC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H9NO4/c1-6-3(5(9)10)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)(H,9,10)/t3-/m1/s1</inchi>
  <inchikey>HOKKHZGPKSLGJE-GSVOUGTGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <direct_parent>Aspartic acid 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>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>D-alpha-amino acids</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Aspartic acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>D-alpha-amino acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</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>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>D-alpha-amino acid</external_descriptor>
      <external_descriptor>D-aspartic acid derivative</external_descriptor>
      <external_descriptor>amino dicarboxylic acid</external_descriptor>
      <external_descriptor>secondary amino compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.06e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-3.3</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>10.34</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2R)-2-(methylamino)butanedioic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>147.1293</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>147.053157781</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CN[C@H](CC(O)=O)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C5H9NO4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C5H9NO4/c1-6-3(5(9)10)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)(H,9,10)/t3-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>HOKKHZGPKSLGJE-GSVOUGTGSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>86.63</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>31.31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>13.18</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</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::MsIr</type>
      <spectrum_id>1762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2100</spectrum_id>
    </spectrum>
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      <type>Specdb::MsMs</type>
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    </spectrum>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2235953</spectrum_id>
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      <type>Specdb::MsMs</type>
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      <type>Specdb::CMs</type>
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      <type>Specdb::CMs</type>
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    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>139295</spectrum_id>
    </spectrum>
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      <type>Specdb::NmrTwoD</type>
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    </spectrum>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::NmrOneD</type>
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      <spectrum_id>122443</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>122444</spectrum_id>
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      <spectrum_id>122455</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>166348</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>166544</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB02393</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id>OEM</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce32f3c680&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f3c3d8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f3c1a8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f37f40&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f37d88&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f360c8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f34890&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f34548&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f34390&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f341d8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f34020&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f2fe08&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f2fc50&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f2fa98&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f2f8e0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f2f728&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f2f520&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Milk (Cow)</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>A-kinase anchor protein 9</name>
      <uniprot_id>Q99996</uniprot_id>
      <uniprot_name/>
      <gene_name>AKAP9</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
