<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:24 UTC</creation_date>
  <update_date>2020-05-11 20:43:59 UTC</update_date>
  <accession>BMDB0000600</accession>
  <secondary_accessions>
    <accession>BMDB00600</accession>
  </secondary_accessions>
  <name>Galactosylhydroxylysine</name>
  <description/>
  <synonyms>
    <synonym>5-(beta-D-Galactopyranosyloxy)-L-lysine</synonym>
    <synonym>5-(beta-delta-Galactopyranosyloxy)-L-lysine</synonym>
    <synonym>5-O-beta-D-Galactopyranosylhydroxy-L-lysine</synonym>
    <synonym>5-O-beta-delta-Galactopyranosylhydroxy-L-lysine</synonym>
    <synonym>beta-1-Galactosyl-O-hydroxylysine</synonym>
    <synonym>Galactopyranosylhydroxy-L-lysine</synonym>
    <synonym>Galactosyl-delta-hydroxylysine</synonym>
    <synonym>Hydroxylysine-galactose</synonym>
    <synonym>L-5-(beta-D-Galactopyranosyloxy)-lysine</synonym>
    <synonym>L-5-(beta-delta-Galactopyranosyloxy)-lysine</synonym>
    <synonym>O-beta-D-Galactopyranosylhydroxy-L-lysine</synonym>
    <synonym>O-beta-delta-Galactopyranosylhydroxy-L-lysine</synonym>
    <synonym>Procollagen (5-galactosyloxy)-L-lysine</synonym>
    <synonym>(2S)-6-Amino-2-{n-hydroxy[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}hexanoate</synonym>
  </synonyms>
  <chemical_formula>C12H24N2O8</chemical_formula>
  <average_molecular_weight>324.3276</average_molecular_weight>
  <monisotopic_moleculate_weight>324.153265754</monisotopic_moleculate_weight>
  <iupac_name>(2S)-6-amino-2-{N-hydroxy[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}hexanoic acid</iupac_name>
  <traditional_iupac>galactosylhydroxylysine</traditional_iupac>
  <cas_registry_number>32448-36-5</cas_registry_number>
  <smiles>NCCCC[C@H](N(O)C1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)C(O)=O</smiles>
  <inchi>InChI=1S/C12H24N2O8/c13-4-2-1-3-6(12(19)20)14(21)11-10(18)9(17)8(16)7(5-15)22-11/h6-11,15-18,21H,1-5,13H2,(H,19,20)/t6-,7+,8-,9-,10+,11?/m0/s1</inchi>
  <inchikey>RCPOVANIIKXVTB-YPPRVYOWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycosyl-amino acids. Glycosyl-amino acids are compounds consisting of saccharide linked through a glycosyl linkage (O-, N-, or S-) to an amino acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Glycosyl-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heterocyclic fatty acids</alternative_parent>
      <alternative_parent>Hexoses</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>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-hydroxyl-alpha-amino acids</alternative_parent>
      <alternative_parent>N-organohydroxylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen 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>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Glycosyl-amino-acid</substituent>
      <substituent>Heterocyclic fatty acid</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-hydroxyl-alpha-amino acid</substituent>
      <substituent>N-organohydroxylamine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>257.0 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-6-amino-2-{N-hydroxy[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}hexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>324.3276</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>324.153265754</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCC[C@H](N(O)C1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H24N2O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H24N2O8/c13-4-2-1-3-6(12(19)20)14(21)11-10(18)9(17)8(16)7(5-15)22-11/h6-11,15-18,21H,1-5,13H2,(H,19,20)/t6-,7+,8-,9-,10+,11?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RCPOVANIIKXVTB-YPPRVYOWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>176.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</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>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>102723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>102724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>102725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>168591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>168592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>168593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2701225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2701226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2701227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3007373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3007374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3007375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>136867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>144601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1069730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>144529</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Platelet</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089.</reference_text>
          <pubmed_id>29140435</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C05547</kegg_id>
  <foodb_id>FDB112162</foodb_id>
  <chemspider_id>17215976</chemspider_id>
  <pubchem_compound_id>22833535</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>165859</chebi_id>
  <drugbank_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5576</metlin_id>
  <synthesis_reference>Adamczyk, Maciej; Reddy, Rajarathnam E.; Rege, Sushil D. Synthesis of galactosylhydroxylysine and its analogs. Synthetic Communications (2000), 30(18), 3281-3290.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
