<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:43 UTC</creation_date>
  <update_date>2020-05-21 16:28:30 UTC</update_date>
  <accession>BMDB0001422</accession>
  <secondary_accessions>
    <accession>BMDB01422</accession>
  </secondary_accessions>
  <name>3-Hydroxy-N6,N6,N6-trimethyl-L-lysine</name>
  <description>3-Hydroxy-N6,N6,N6-trimethyl-L-lysine belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine exists in all living organisms, ranging from bacteria to humans. 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine participates in a number of enzymatic reactions, within cattle. In particular, 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine and succinic acid can be biosynthesized from N6,N6,N6-trimethyl-L-lysine and oxoglutaric acid through its interaction with the enzyme trimethyllysine dioxygenase, mitochondrial. In addition, 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine can be converted into glycine and 4-trimethylammoniobutanal; which is mediated by the enzyme serine hydroxymethyltransferase, cytosolic. In cattle, 3-hydroxy-N6,N6,N6-trimethyl-L-lysine is involved in the metabolic pathway called carnitine synthesis pathway.</description>
  <synonyms>
    <synonym>3-Hydroxy-N(6),N(6),N(6)-trimethyl-L-lysine</synonym>
    <synonym>3-Hydroxy-N(6),N(6),N(6)-trimethyllysine</synonym>
    <synonym>3-Hydroxy-N6,N6,N6-trimethyl-L-lysin-N6-ium</synonym>
  </synonyms>
  <chemical_formula>C9H21N2O3</chemical_formula>
  <average_molecular_weight>205.2746</average_molecular_weight>
  <monisotopic_moleculate_weight>205.155217548</monisotopic_moleculate_weight>
  <iupac_name>[(5S)-5-amino-5-carboxy-4-hydroxypentyl]trimethylazanium</iupac_name>
  <traditional_iupac>[(5S)-5-amino-5-carboxy-4-hydroxypentyl]trimethylazanium</traditional_iupac>
  <cas_registry_number/>
  <smiles>C[N+](C)(C)CCCC(O)[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C9H20N2O3/c1-11(2,3)6-4-5-7(12)8(10)9(13)14/h7-8,12H,4-6,10H2,1-3H3/p+1/t7?,8-/m0/s1</inchi>
  <inchikey>ZRJHLGYVUCPZNH-MQWKRIRWSA-O</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</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>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Medium-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>alpha-amino-acid cation</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(5S)-5-amino-5-carboxy-4-hydroxypentyl]trimethylazanium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>205.2746</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>205.155217548</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)CCCC(O)[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H21N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H20N2O3/c1-11(2,3)6-4-5-7(12)8(10)9(13)14/h7-8,12H,4-6,10H2,1-3H3/p+1/t7?,8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZRJHLGYVUCPZNH-MQWKRIRWSA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>83.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>65.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</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>1</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>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>157435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2326293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2326294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2326295</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01259</kegg_id>
  <chemspider_id>388565</chemspider_id>
  <foodb_id>FDB022613</foodb_id>
  <pubchem_compound_id>439460</pubchem_compound_id>
  <drugbank_id/>
  <knapsack_id/>
  <pdbe_id/>
  <chebi_id>15786</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>37211</bigg_id>
  <wikipedia_id/>
  <metlin_id>6234</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00087</protein_accession>
      <name>Serine hydroxymethyltransferase, cytosolic</name>
      <uniprot_id>Q5E9P9</uniprot_id>
      <gene_name>SHMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00622</protein_accession>
      <name>Trimethyllysine dioxygenase, mitochondrial</name>
      <uniprot_id>Q0VC74</uniprot_id>
      <gene_name>TMLHE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
