<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 01:39:30 UTC</creation_date>
  <update_date>2019-11-26 03:21:28 UTC</update_date>
  <accession>FDB028419</accession>
  <name>N-Acetyl-D-mannosamine</name>
  <description>N-Acetylmannosamine is a monosaccharide involved in a range of metabolic processes. It is an amino sugar/amino acid that consists of neuraminic acids, glycolipids and glycoproteins, and is used for the synthesis of sialic acid. [Wikipedia]</description>
  <synonyms>
    <synonym>2-acetamido-2-Deoxy-D-mannopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-D-mannose</synonym>
    <synonym>b-ManNAc</synonym>
    <synonym>beta-ManNAc</synonym>
    <synonym>ManNAc</synonym>
    <synonym>N-Acetyl-b-mannosamine</synonym>
    <synonym>N-Acetyl-beta-mannosamine</synonym>
    <synonym>N-Acetyl-D-mannosamine</synonym>
    <synonym>N-Acetyl-β-mannosamine</synonym>
    <synonym>N-Acetylmannosamine</synonym>
    <synonym>β-mannac</synonym>
  </synonyms>
  <chemical_formula>C8H15NO6</chemical_formula>
  <average_molecular_weight>221.2078</average_molecular_weight>
  <monisotopic_moleculate_weight>221.089937217</monisotopic_moleculate_weight>
  <iupac_name>N-[(2S,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide</iupac_name>
  <traditional_iupac>2-acetamido-2-deoxy-d-glucose</traditional_iupac>
  <cas_registry_number>7772-94-3</cas_registry_number>
  <smiles>[H][C@@](O)(CO)[C@@]([H])(O)[C@]([H])(O)[C@]([H])(NC(C)=O)C=O</smiles>
  <inchi>InChI=1S/C8H15NO6/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11/h2,5-8,11,13-15H,3H2,1H3,(H,9,12)/t5-,6-,7-,8-/m1/s1</inchi>
  <inchikey>MBLBDJOUHNCFQT-WCTZXXKLSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <direct_parent>Hexoses</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Aminosaccharides</alternative_parent>
      <alternative_parent>Beta-hydroxy aldehydes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amino saccharide</substituent>
      <substituent>Beta-hydroxy aldehyde</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.48e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-3.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>12.09</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-1.8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>N-[(2S,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>221.2078</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>221.089937217</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>[H][C@@](O)(CO)[C@@]([H])(O)[C@]([H])(O)[C@]([H])(NC(C)=O)C=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C8H15NO6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C8H15NO6/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11/h2,5-8,11,13-15H,3H2,1H3,(H,9,12)/t5-,6-,7-,8-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>MBLBDJOUHNCFQT-WCTZXXKLSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>127.09</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>48.45</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>20.82</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>5</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>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP00045</smpdb_id>
      <kegg_map_id>map00520</kegg_map_id>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>48941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280043</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB01129</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>63154</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce320cc370&gt;</reference>
    <reference>#&lt;Reference:0x000055ce320cc1b8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce320cc3e8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce320dfe70&gt;</reference>
    <reference>#&lt;Reference:0x000055ce320dfc90&gt;</reference>
    <reference>#&lt;Reference:0x000055ce320dfad8&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Milk (Cow)</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>14 kDa phosphohistidine phosphatase</name>
      <uniprot_id>Q9NRX4</uniprot_id>
      <uniprot_name/>
      <gene_name>PHPT1</gene_name>
    </enzyme>
    <enzyme>
      <name>Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase</name>
      <uniprot_id>Q9Y223</uniprot_id>
      <uniprot_name/>
      <gene_name>GNE</gene_name>
    </enzyme>
    <enzyme>
      <name>N-acetylneuraminate lyase</name>
      <uniprot_id>Q9BXD5</uniprot_id>
      <uniprot_name/>
      <gene_name>NPL</gene_name>
    </enzyme>
    <enzyme>
      <name>N-acylglucosamine 2-epimerase</name>
      <uniprot_id>P51606</uniprot_id>
      <uniprot_name/>
      <gene_name>RENBP</gene_name>
    </enzyme>
    <enzyme>
      <name>Sialic acid synthase</name>
      <uniprot_id>Q9NR45</uniprot_id>
      <uniprot_name/>
      <gene_name>NANS</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
