<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 23:25:59 UTC</creation_date>
  <update_date>2020-05-21 16:28:41 UTC</update_date>
  <accession>BMDB0006790</accession>
  <secondary_accessions>
    <accession>BMDB06790</accession>
  </secondary_accessions>
  <name>Galactosylglycerol</name>
  <description>Galactosylglycerol, also known as galactosylglycerol, belongs to the class of organic compounds known as glycosylglycerols. These are glycerolipids structurally characterized by the presence of one or more sugar residues attached to glycerol via a glycosidic linkage. Galactosylglycerol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Galactosylglycerol exists in all living species, ranging from bacteria to humans. Galactosylglycerol can be biosynthesized from D-galactose and glycerol; which is catalyzed by the enzyme Alpha-galactosidase a. In cattle, galactosylglycerol is involved in the metabolic pathway called the galactose metabolism pathway.</description>
  <synonyms>
    <synonym>(2R,3R,4S,5R,6R)-2-[(2R)-2,3-Dihydroxypropoxy]-6-(hydroxymethyl)oxane-3,4,5-triol</synonym>
    <synonym>3-b-D-Galactosyl-sn-glycerol</synonym>
    <synonym>3-beta-D-Galactosyl-sn-glycerol</synonym>
    <synonym>3-beta-delta-Galactosyl-sn-glycerol</synonym>
    <synonym>Azepan-2-one</synonym>
  </synonyms>
  <chemical_formula>C9H18O8</chemical_formula>
  <average_molecular_weight>254.2344</average_molecular_weight>
  <monisotopic_moleculate_weight>254.100167552</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4S,5R,6R)-2-(2,3-dihydroxypropoxy)-6-(hydroxymethyl)oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>galactosylglycerol</traditional_iupac>
  <cas_registry_number/>
  <smiles>OCC(O)CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C9H18O8/c10-1-4(12)3-16-9-8(15)7(14)6(13)5(2-11)17-9/h4-15H,1-3H2/t4?,5-,6+,7+,8-,9-/m1/s1</inchi>
  <inchikey>NHJUPBDCSOGIKX-VGPGGAHRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycosylglycerols. These are glycerolipids structurally characterized by the presence of one or more sugar residues attached to glycerol via a glycosidic linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerolipids</class>
    <sub_class>Glycosylglycerols</sub_class>
    <direct_parent>Glycosylglycerols</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Glycosylglycerol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R,4S,5R,6R)-2-(2,3-dihydroxypropoxy)-6-(hydroxymethyl)oxane-3,4,5-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>254.2344</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>254.100167552</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(O)CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H18O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H18O8/c10-1-4(12)3-16-9-8(15)7(14)6(13)5(2-11)17-9/h4-15H,1-3H2/t4?,5-,6+,7+,8-,9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NHJUPBDCSOGIKX-VGPGGAHRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>139.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>52.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</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>
    <property>
      <kind>number_of_rings</kind>
      <value>1</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>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>39087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>131626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>139360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2266719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2266720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2266721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3075672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3075673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3075674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>91391</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB024079</foodb_id>
  <chemspider_id>570889</chemspider_id>
  <chebi_id>15754</chebi_id>
  <pubchem_compound_id>656504</pubchem_compound_id>
  <kegg_id>C05401</kegg_id>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP02909</protein_accession>
      <name>Alpha-N-acetylgalactosaminidase</name>
      <uniprot_id>Q58DH9</uniprot_id>
      <gene_name>NAGA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
