<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:04:55 UTC</creation_date>
  <update_date>2019-11-26 03:21:00 UTC</update_date>
  <accession>FDB021904</accession>
  <name>L-Acetylcarnitine</name>
  <description>An acetic acid ester of carnitine that facilitates movement of acetyl CoA into the matrices of mammalian mitochondria during the oxidation of fatty acids. In addition to his metabolic role, acetyl-L-carnitine (ALC) posses unique neuroprotective, neuromodulatory, and neurotrophic properties this may play an important role in counteracting various disease processes.  (PubMed ID 15363640) [HMDB]</description>
  <synonyms>
    <synonym>(-)-Acetylcarnitine</synonym>
    <synonym>(+-)-Acetylcarnitine</synonym>
    <synonym>(R)-Acetylcarnitine</synonym>
    <synonym>3-(Acetyloxy)-4-(trimethylammonio)butanoate</synonym>
    <synonym>3-(Acetyloxy)-4-(trimethylammonio)butanoic acid</synonym>
    <synonym>Acetyl-carnitine</synonym>
    <synonym>Acetyl-DL-carnitine</synonym>
    <synonym>Acetyl-L-(-)-carnitine</synonym>
    <synonym>Acetyl-L-carnitine</synonym>
    <synonym>Acetylcarnitine</synonym>
    <synonym>ALCAR</synonym>
    <synonym>DL-O-Acetylcarnitine</synonym>
    <synonym>L-Acetylcarnitine</synonym>
    <synonym>L-Carnitine acetyl ester</synonym>
    <synonym>L-O-Acetylcarnitine</synonym>
    <synonym>Levocarnitine acetyl</synonym>
    <synonym>Nicetile</synonym>
    <synonym>O-Acetyl-L-carnitine</synonym>
    <synonym>O-Acetylcarnitine</synonym>
  </synonyms>
  <chemical_formula>C9H17NO4</chemical_formula>
  <average_molecular_weight>203.2356</average_molecular_weight>
  <monisotopic_moleculate_weight>203.115758037</monisotopic_moleculate_weight>
  <iupac_name>3-(acetyloxy)-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>alcar</traditional_iupac>
  <cas_registry_number>3040-38-8</cas_registry_number>
  <smiles>CC(=O)OC(CC([O-])=O)C[N+](C)(C)C</smiles>
  <inchi>InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3</inchi>
  <inchikey>RDHQFKQIGNGIED-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.</description>
    <direct_parent>Acyl carnitines</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl-carnitine</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</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>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>O-acylcarnitine</external_descriptor>
      <external_descriptor>an &lt;i&gt;O&lt;/i&gt;-acyl-L-carnitine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.55e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-4.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>4.09</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>3-(acetyloxy)-4-(trimethylazaniumyl)butanoate</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>203.2356</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>203.115758037</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(=O)OC(CC([O-])=O)C[N+](C)(C)C</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C9H17NO4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>RDHQFKQIGNGIED-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>66.43</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>72.64</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>20.88</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>0</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>Beta Oxidation of Very Long Chain Fatty Acids</name>
      <smpdb_id>SMP00052</smpdb_id>
      <kegg_map_id>map01040</kegg_map_id>
    </pathway>
    <pathway>
      <name>Oxidation of Branched Chain Fatty Acids</name>
      <smpdb_id>SMP00030</smpdb_id>
      <kegg_map_id></kegg_map_id>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2435461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2435462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2435463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>168559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>77071</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB00201</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce31fc19a8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fc17f0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fc1638&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fc1480&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fc12a0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fc10c0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fc0eb8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fc0cd8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fc0b20&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fc0940&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fc0788&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fc05d0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fc0418&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fc0260&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fc00a8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fbfea0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fbfce8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fbfb30&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fbf978&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fbf7c0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31fbf608&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Cow milk, pasteurized, vitamin A + D added, 0% fat</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Cow milk, pasteurized, vitamin A + D added, 1% fat</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Cow milk, pasteurized, vitamin A + D added, 2% fat</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Cow milk, pasteurized, vitamin D added, 3.25% fat</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Milk (Cow)</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
      <average_value>43.289333</average_value>
      <max_value>51.71</max_value>
      <min_value>37.0</min_value>
      <unit>uM</unit>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Carnitine O-acetyltransferase</name>
      <uniprot_id>P43155</uniprot_id>
      <uniprot_name/>
      <gene_name>CRAT</gene_name>
    </enzyme>
    <enzyme>
      <name>Mitochondrial carnitine/acylcarnitine carrier protein</name>
      <uniprot_id>O43772</uniprot_id>
      <uniprot_name/>
      <gene_name>SLC25A20</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
