<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 01:31:22 UTC</creation_date>
  <update_date>2017-04-03 05:02:17 UTC</update_date>
  <accession>FDB027881</accession>
  <name>(R)-3-Hydroxy-hexadecanoic acid</name>
  <description>In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. (R)-3-Hydroxy-hexadecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, (R)-3-Hydroxy-hexadecanoic acid is converted from 3-Oxo-tetradecanoic acid via fatty-acid Synthase and 3-oxoacyl- [acyl-carrier-protein] reductase. (EC: 2.3.1.85 and EC: 2.3.1.41) [HMDB]</description>
  <synonyms>
    <synonym>(R)-b-Hydroxypalmitate</synonym>
    <synonym>(R)-b-Hydroxypalmitic acid</synonym>
    <synonym>(R)-beta-Hydroxypalmitate</synonym>
    <synonym>(R)-beta-Hydroxypalmitic acid</synonym>
    <synonym>(R)-β-hydroxypalmitate</synonym>
    <synonym>(R)-β-hydroxypalmitic acid</synonym>
  </synonyms>
  <chemical_formula>C16H32O3</chemical_formula>
  <average_molecular_weight>272.4235</average_molecular_weight>
  <monisotopic_moleculate_weight>272.23514489</monisotopic_moleculate_weight>
  <iupac_name>(3R)-3-hydroxyhexadecanoic acid</iupac_name>
  <traditional_iupac>(R)-3-hydroxypalmitic acid</traditional_iupac>
  <cas_registry_number>2398-34-7</cas_registry_number>
  <smiles>[H][C@@](O)(CCCCCCCCCCCCC)CC(O)=O</smiles>
  <inchi>InChI=1S/C16H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15(17)14-16(18)19/h15,17H,2-14H2,1H3,(H,18,19)/t15-/m1/s1</inchi>
  <inchikey>CBWALJHXHCJYTE-OAHLLOKOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <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>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>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Long-chain fatty 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>
    <external_descriptors>
      <external_descriptor>(3R)-3-hydroxy fatty acid</external_descriptor>
      <external_descriptor>3-hydroxypalmitic acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.58e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>5.03</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-hydroxyhexadecanoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>272.4235</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>272.23514489</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>[H][C@@](O)(CCCCCCCCCCCCC)CC(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C16H32O3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C16H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15(17)14-16(18)19/h15,17H,2-14H2,1H3,(H,18,19)/t15-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>CBWALJHXHCJYTE-OAHLLOKOSA-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>78.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>35.11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>14</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>
  <pathways>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP00456</smpdb_id>
      <kegg_map_id></kegg_map_id>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>39541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>137747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>145481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>305050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2325261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2325262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2325263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2610422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2610423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2610424</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB10734</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Anatidae</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anatidae</name_scientific>
      <ncbi_taxonomy_id>8830</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Beefalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus X Bison bison</name_scientific>
      <ncbi_taxonomy_id>297284</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Bison</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bison bison</name_scientific>
      <ncbi_taxonomy_id>9901</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Buffalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bubalus bubalis</name_scientific>
      <ncbi_taxonomy_id>89462</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cattle (Beef, Veal)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus</name_scientific>
      <ncbi_taxonomy_id>9913</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Chicken</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Gallus gallus</name_scientific>
      <ncbi_taxonomy_id>9031</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Columbidae (Dove, Pigeon)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columbidae</name_scientific>
      <ncbi_taxonomy_id>8930</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervidae</name_scientific>
      <ncbi_taxonomy_id>9850</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic goat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capra aegagrus hircus</name_scientific>
      <ncbi_taxonomy_id>9925</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic pig</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa domestica</name_scientific>
      <ncbi_taxonomy_id>9825</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Elk</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervus canadensis</name_scientific>
      <ncbi_taxonomy_id>1574408</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Emu</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Dromaius novaehollandiae</name_scientific>
      <ncbi_taxonomy_id>8790</ncbi_taxonomy_id>
    </food>
    <food>
      <name>European rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryctolagus</name_scientific>
      <ncbi_taxonomy_id>9984</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Greylag goose</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anser anser</name_scientific>
      <ncbi_taxonomy_id>8843</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Guinea hen</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Numida meleagris</name_scientific>
      <ncbi_taxonomy_id>8996</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Horse</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Equus caballus</name_scientific>
      <ncbi_taxonomy_id>9796</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mallard duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anas platyrhynchos</name_scientific>
      <ncbi_taxonomy_id>8839</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mountain hare</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lepus timidus</name_scientific>
      <ncbi_taxonomy_id>62621</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mule deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Odocoileus</name_scientific>
      <ncbi_taxonomy_id>9871</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Ostrich</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Struthio camelus</name_scientific>
      <ncbi_taxonomy_id>8801</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pheasant</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianus colchicus</name_scientific>
      <ncbi_taxonomy_id>9054</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Quail</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianidae</name_scientific>
      <ncbi_taxonomy_id>9005</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Leporidae</name_scientific>
      <ncbi_taxonomy_id>9979</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rock ptarmigan</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lagopus muta</name_scientific>
      <ncbi_taxonomy_id>64668</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sheep (Mutton, Lamb)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ovis aries</name_scientific>
      <ncbi_taxonomy_id>9940</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Squab</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columba</name_scientific>
      <ncbi_taxonomy_id>8931</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Turkey</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Meleagris gallopavo</name_scientific>
      <ncbi_taxonomy_id>9103</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Velvet duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Melanitta fusca</name_scientific>
      <ncbi_taxonomy_id>371864</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild boar</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa</name_scientific>
      <ncbi_taxonomy_id>9823</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>3-oxoacyl-[acyl-carrier-protein] synthase, mitochondrial</name>
      <uniprot_id>Q9NWU1</uniprot_id>
      <uniprot_name/>
      <gene_name>OXSM</gene_name>
    </enzyme>
    <enzyme>
      <name>Fatty acid synthase</name>
      <uniprot_id>P49327</uniprot_id>
      <uniprot_name/>
      <gene_name>FASN</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
