<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 23:04:52 UTC</creation_date>
  <update_date>2020-04-22 15:12:22 UTC</update_date>
  <accession>BMDB0003470</accession>
  <secondary_accessions>
    <accession>BMDB03470</accession>
  </secondary_accessions>
  <name>N-Formyl-L-glutamic acid</name>
  <description>N-Formyl-L-glutamic acid, also known as N-formyl-L-glutamate, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Formyl-L-glutamic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Formyl-L-glutamic acid exists in all living organisms, ranging from bacteria to humans. Tetrahydrofolic acid and N-formyl-L-glutamic acid can be biosynthesized from N5-formyl-THF and L-glutamic acid; which is mediated by the enzyme formimidoyltransferase-cyclodeaminase. In cattle, N-formyl-L-glutamic acid is involved in the metabolic pathway called the folate metabolism pathway.</description>
  <synonyms>
    <synonym>(2S)-2-(Formylamino)pentanedioic acid</synonym>
    <synonym>N-Formyl-L-glutamate</synonym>
    <synonym>(2S)-2-(Formylamino)pentanedioate</synonym>
    <synonym>N-Formylglutamate, ion(2-)</synonym>
    <synonym>N-Formylglutamate</synonym>
    <synonym>(2S)-2-Formamidopentanedioate</synonym>
    <synonym>(2S)-2-Formamidopentanedioic acid</synonym>
  </synonyms>
  <chemical_formula>C6H9NO5</chemical_formula>
  <average_molecular_weight>175.1394</average_molecular_weight>
  <monisotopic_moleculate_weight>175.048072403</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-formamidopentanedioic acid</iupac_name>
  <traditional_iupac>N-formyl-L-glutamic acid</traditional_iupac>
  <cas_registry_number>1681-96-5</cas_registry_number>
  <smiles>OC(=O)CC[C@H](NC=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H9NO5/c8-3-7-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t4-/m0/s1</inchi>
  <inchikey>ADZLWSMFHHHOBV-BYPYZUCNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <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>Glutamic acid and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</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>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>N-formyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>N-formyl-alpha amino acid or derivatives</substituent>
      <substituent>N-formyl-alpha-amino acid</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 carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acyl-L-glutamic acid</external_descriptor>
      <external_descriptor>N-formyl amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-formamidopentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>175.1394</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>175.048072403</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC[C@H](NC=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H9NO5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H9NO5/c8-3-7-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t4-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ADZLWSMFHHHOBV-BYPYZUCNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>103.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>36.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</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>-2</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>
  <pathways>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>175304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2797718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2797719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2797720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2880494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2880495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2880496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>149579</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB023180</foodb_id>
  <drugbank_id/>
  <chemspider_id>388496</chemspider_id>
  <kegg_id>C01045</kegg_id>
  <pubchem_compound_id>439376</pubchem_compound_id>
  <chebi_id>48309</chebi_id>
  <knapsack_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6939</metlin_id>
  <synthesis_reference>Borek, Blanche Ann; Waelsch, Heinrich.  The enzymic degradation of histidine.    Journal of Biological Chemistry  (1953),  205  459-74.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
