<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:31:50 UTC</creation_date>
  <update_date>2015-10-09 22:33:02 UTC</update_date>
  <accession>FDB023575</accession>
  <name>Guaifenesin</name>
  <description>Guaifenesin (INN) or guaiphenesin (former BAN) is an expectorant drug usually taken orally to assist the expectoration ('bringing up') of phlegm from the airways in acute respiratory tract infections.  It is a common ingredient in many over-the-counter cough/cold medications. Guaifenesin is also used in the experimental guaifenesin protocol in the treatment of fibromyalgia. It was first approved by the Food and Drug Administration (FDA) in 1952. Guaifenesin works by drawing water into the bronchi. The water both thins mucus and lubricates the airway, facilitating the removal of mucus by coughing. [HMDB]</description>
  <synonyms>
    <synonym>3-(2-Methoxyphenoxy)-1,2-propanediol</synonym>
    <synonym>3-(o-Methoxyphenoxy)-1,2-propanediol</synonym>
    <synonym>3-(o-Methoxyphenoxy)-propanediol-1,2</synonym>
    <synonym>3-o-Methoxyphenoxypropane 1:2-diol</synonym>
    <synonym>a-Glyceryl guaiacol ether</synonym>
    <synonym>a-Glyceryl guaiacolate ether</synonym>
    <synonym>Actifed C</synonym>
    <synonym>Aeronesin</synonym>
    <synonym>alpha-Glyceryl guaiacol ether</synonym>
    <synonym>alpha-Glyceryl guaiacolate ether</synonym>
    <synonym>Amonidren</synonym>
    <synonym>Amonidrin</synonym>
    <synonym>Aresol</synonym>
    <synonym>Benylin-E</synonym>
    <synonym>Bronchol</synonym>
    <synonym>glycerin ether</synonym>
    <synonym>Glycerin guaiacolate</synonym>
    <synonym>Glycero-guaiacol ether</synonym>
    <synonym>Glycerol a-(2-methoxyphenyl) ether</synonym>
    <synonym>Glycerol a-(o-methoxyphenyl)ether</synonym>
    <synonym>Glycerol a-guaiacyl ether</synonym>
    <synonym>Glycerol a-guiacyl ether</synonym>
    <synonym>Glycerol a-monoguaiacol ether</synonym>
    <synonym>Glycerol guaiacolate</synonym>
    <synonym>Glycerol mono(2-methoxyphenyl) ether</synonym>
    <synonym>Glycerol-a-guajakolether</synonym>
    <synonym>Glycerol-alpha-guajakolether</synonym>
    <synonym>Glyceryl guaiacol</synonym>
    <synonym>Glyceryl guaiacol ether</synonym>
    <synonym>Glyceryl guaiacolate</synonym>
    <synonym>Glyceryl guaiacolate ether</synonym>
    <synonym>Glyceryl guaiacyl ether</synonym>
    <synonym>Glyceryl guaicolate</synonym>
    <synonym>Glyceryl guiacolate</synonym>
    <synonym>Glycerylguaiacol</synonym>
    <synonym>Guaiacol glycerol ether</synonym>
    <synonym>Guaiacol glyceryl ether</synonym>
    <synonym>Guaiacolglicerinetere</synonym>
    <synonym>Guaiacuran</synonym>
    <synonym>Guaiacurane</synonym>
    <synonym>Guaiacyl glyceryl ether</synonym>
    <synonym>Guaiamar</synonym>
    <synonym>Guaianesin</synonym>
    <synonym>Guaicol glycerine ether</synonym>
    <synonym>Guaicol glyceryl ether</synonym>
    <synonym>Guaifenesin</synonym>
    <synonym>Guaifenesine</synonym>
    <synonym>Guaiphenesin</synonym>
    <synonym>Guaiphenesine</synonym>
    <synonym>Guaiphesin</synonym>
    <synonym>Hustosil</synonym>
    <synonym>Methoxypropanediol</synonym>
    <synonym>Methphenoxydiol</synonym>
    <synonym>Metossipropandiolo</synonym>
    <synonym>o-Methoxyphenyl glyceryl ether</synonym>
    <synonym>Organidin NR</synonym>
    <synonym>Pneumomist</synonym>
    <synonym>Propanosedyl</synonym>
    <synonym>Reduton</synonym>
    <synonym>Robitussin</synonym>
  </synonyms>
  <chemical_formula>C10H14O4</chemical_formula>
  <average_molecular_weight>198.2158</average_molecular_weight>
  <monisotopic_moleculate_weight>198.089208936</monisotopic_moleculate_weight>
  <iupac_name>3-(2-methoxyphenoxy)propane-1,2-diol</iupac_name>
  <traditional_iupac>guaifenesin</traditional_iupac>
  <cas_registry_number>93-14-1</cas_registry_number>
  <smiles>COC1=CC=CC=C1OCC(O)CO</smiles>
  <inchi>InChI=1S/C10H14O4/c1-13-9-4-2-3-5-10(9)14-7-8(12)6-11/h2-5,8,11-12H,6-7H2,1H3</inchi>
  <inchikey>HSRJKNPTNIJEKV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.</description>
    <direct_parent>Anisoles</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenol ethers</class>
    <sub_class>Anisoles</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.49e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.34</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>13.62</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>3-(2-methoxyphenoxy)propane-1,2-diol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>198.2158</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>198.089208936</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=CC=CC=C1OCC(O)CO</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H14O4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H14O4/c1-13-9-4-2-3-5-10(9)14-7-8(12)6-11/h2-5,8,11-12H,6-7H2,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>HSRJKNPTNIJEKV-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>58.92</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>51.24</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>20.59</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>2</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>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>2276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>2277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>2278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>121187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>146327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>829061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>829062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>829063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>829064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>829065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>104907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>104908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>104909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2427106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2427107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2427108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2512035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2512036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2512037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54882</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>54901</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB04998</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:0x000055ce31cef310&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
    <flavor>
      <name>bitter</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
