<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-10-03 18:12:35 UTC</creation_date>
  <update_date>2020-05-21 16:27:15 UTC</update_date>
  <accession>BMDB0010725</accession>
  <secondary_accessions>
    <accession>BMDB10725</accession>
  </secondary_accessions>
  <name>(R)-3-Hydroxydecanoic acid</name>
  <description>(R)-3-Hydroxydecanoic acid, also known as (r)-(r)-(r)-3-hydroxydecanoic acid or (r)-3-hydroxydecanoic acid, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain (R)-3-Hydroxydecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (R)-3-Hydroxydecanoic acid exists in all eukaryotes, ranging from yeast to humans (R)-3-Hydroxydecanoic acid participates in a number of enzymatic reactions, within cattle. In particular, (R)-3-Hydroxydecanoic acid can be biosynthesized from 3-oxodecanoic acid through the action of the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In addition, (R)-3-Hydroxydecanoic acid can be converted into trans-dec-2-enoic acid through the action of the enzyme fatty acid synthase. dyhydrase domain. In cattle, (R)-(r)-(r)-3-hydroxydecanoic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway.</description>
  <synonyms>
    <synonym>(R)-3-Hydroxydecanoate</synonym>
    <synonym>3-HDA</synonym>
    <synonym>3-Hydroxydecanoic acid</synonym>
    <synonym>beta-Hydroxydecanoic acid</synonym>
    <synonym>Myrmicacin, (+-)-isomer</synonym>
    <synonym>Myrmicacin monosodium (+-)-isomer</synonym>
    <synonym>3-Hydroxy-decanoic acid</synonym>
    <synonym>Myrmicacin, (R)-isomer</synonym>
    <synonym>Myrmicacin</synonym>
  </synonyms>
  <chemical_formula>C10H20O3</chemical_formula>
  <average_molecular_weight>188.264</average_molecular_weight>
  <monisotopic_moleculate_weight>188.141244506</monisotopic_moleculate_weight>
  <iupac_name>(3R)-3-hydroxydecanoic acid</iupac_name>
  <traditional_iupac>(R)-3-hydroxydecanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@](O)(CCCCCCC)CC(O)=O</smiles>
  <inchi>InChI=1S/C10H20O3/c1-2-3-4-5-6-7-9(11)8-10(12)13/h9,11H,2-8H2,1H3,(H,12,13)/t9-/m1/s1</inchi>
  <inchikey>FYSSBMZUBSBFJL-SECBINFHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Medium-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Medium-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <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>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R)-3-hydroxydecanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>188.264</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>188.141244506</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](O)(CCCCCCC)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H20O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H20O3/c1-2-3-4-5-6-7-9(11)8-10(12)13/h9,11H,2-8H2,1H3,(H,12,13)/t9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FYSSBMZUBSBFJL-SECBINFHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</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>
    <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>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>39532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>151095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2302932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2302933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2302934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3065318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3065319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3065320</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB027873</foodb_id>
  <chemspider_id>4472223</chemspider_id>
  <drugbank_id/>
  <kegg_id/>
  <pubchem_compound_id>5312798</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00368</protein_accession>
      <name>Fatty acid synthase</name>
      <uniprot_id>Q71SP7</uniprot_id>
      <gene_name>FASN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
