<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:06 UTC</creation_date>
  <update_date>2019-11-26 03:06:34 UTC</update_date>
  <accession>FDB012326</accession>
  <name>Guanosine diphosphate mannose</name>
  <description>Present in egg white. Presumed intermed. in formation of mannan in yeastand is also isolated from green gram (Phaseolus aureus) seedlings

GDP-mannose is a nucleoside diphosphate sugar that is important in the production of fucosylated oligosaccharides. Guanosine diphosphate mannose is found in eggs and pulses.</description>
  <synonyms>
    <synonym>GDP Mannose</synonym>
    <synonym>GDP-D-Mannose</synonym>
    <synonym>GDP-Glucose</synonym>
    <synonym>GDP-mannose</synonym>
    <synonym>GDPmannose</synonym>
    <synonym>Guanosine 5'-(trihydrogen diate), mono-a-D-mannopyranosyl ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen diate), mono-alpha-D-mannopyranosyl ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen diate), mono-α-D-mannopyranosyl ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen diic acid), mono-a-D-mannopyranosyl ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen diic acid), mono-alpha-D-mannopyranosyl ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen diic acid), mono-α-D-mannopyranosyl ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen diphosphate)mono-a-D-mannopyranosyl ester, 9CI</synonym>
    <synonym>Guanosine 5'-(trihydrogen pyrophosphate)mono-a-D-mannopyranosyl ester, 8CI</synonym>
    <synonym>Guanosine diate mannose</synonym>
    <synonym>Guanosine diic acid mannose</synonym>
    <synonym>Guanosine diomannose</synonym>
    <synonym>Guanosine diphosphomannose</synonym>
    <synonym>Guanosine pyroate mannose</synonym>
    <synonym>Guanosine pyroic acid mannose</synonym>
    <synonym>Guanosine pyrophosphate mannose</synonym>
  </synonyms>
  <chemical_formula>C16H25N5O16P2</chemical_formula>
  <average_molecular_weight>605.3411</average_molecular_weight>
  <monisotopic_moleculate_weight>605.077152801</monisotopic_moleculate_weight>
  <iupac_name>[({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>{[3,4-dihydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid</traditional_iupac>
  <cas_registry_number>3123-67-9</cas_registry_number>
  <smiles>OCC1OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C2NC(=N)N=C3O)C(O)C(O)C1O</smiles>
  <inchi>InChI=1S/C16H25N5O16P2/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28)</inchi>
  <inchikey>MVMSCBBUIHUTGJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <direct_parent>Purine nucleotide sugars</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine nucleotide sugars</sub_class>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.63e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-5.8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>1.71</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>3.38</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>[({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>605.3411</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>605.077152801</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OCC1OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C2NC(=N)N=C3O)C(O)C(O)C1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C16H25N5O16P2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C16H25N5O16P2/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>MVMSCBBUIHUTGJ-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>328.42</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>129.09</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>51.01</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>17</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP00064</smpdb_id>
      <kegg_map_id>map00051</kegg_map_id>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21811</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB01163</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>15820</chebi_id>
  <biocyc_id/>
  <het_id>GDD</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce32339590&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Eggs</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Pulses</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Alpha-1,3/1,6-mannosyltransferase ALG2</name>
      <uniprot_id>Q9H553</uniprot_id>
      <uniprot_name/>
      <gene_name>ALG2</gene_name>
    </enzyme>
    <enzyme>
      <name>Chitobiosyldiphosphodolichol beta-mannosyltransferase</name>
      <uniprot_id>Q9BT22</uniprot_id>
      <uniprot_name/>
      <gene_name>ALG1</gene_name>
    </enzyme>
    <enzyme>
      <name>Dolichol-phosphate mannosyltransferase</name>
      <uniprot_id>O60762</uniprot_id>
      <uniprot_name/>
      <gene_name>DPM1</gene_name>
    </enzyme>
    <enzyme>
      <name>GDP-mannose 4,6 dehydratase</name>
      <uniprot_id>O60547</uniprot_id>
      <uniprot_name/>
      <gene_name>GMDS</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
