<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 05:22:10 UTC</creation_date>
  <update_date>2026-08-24 16:32:16 UTC</update_date>
  <accession/>
  <common_name>N-Acetylglucosamine</common_name>
  <class>SmallMolecule</class>
  <description>N-Acetylglucosamine is an organic compound with the formula C8H15NO6 and an average molecular weight of 221.21 g/mol. N-Acetylglucosamine belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds.

This compound is found in or released from ten recorded sources. These include electrical and electronic equipment, specifically amplifiers, television systems, loudspeakers, line transmission systems, adjustable resistors, and one additional source. It is also associated with food, food processing, and cookware, including the processing of fish, the preparation of vinegar, the preparation of wine or sparkling wine, and molasses and the treatment of molasses.

N-Acetylglucosamine interacts with six recorded protein targets. It acts as an activator of Alpha-N-acetylglucosaminidase (NAGLU) and targets N-acylglucosamine 2-epimerase (RENBP), Beta-1,4-galactosyltransferase 1 (B4GALT1), and Beta-1,4-galactosyltransferase 4 (B4GALT4), along with two other proteins.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>N-Acetyl-D-glucosamine</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-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide</iupac_name>
  <traditional_iupac>N acetylglucosamine</traditional_iupac>
  <cas_registry_number>7512-17-6</cas_registry_number>
  <smiles>[H]C(=O)[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@H](O)CO</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+/m0/s1</inchi>
  <inchikey>MBLBDJOUHNCFQT-LXGUWJNJSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexoses</direct_parent>
    <alternate_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>
    </alternate_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>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>N-acetylglucosamine</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0000045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sialuria or French Type Sialuria</name>
      <smpdb_id>SMP0000216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Salla Disease/Infantile Sialic Acid Storage Disease</name>
      <smpdb_id>SMP0000240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tay-Sachs Disease</name>
      <smpdb_id>SMP0000390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sialuria or French Type Sialuria</name>
      <smpdb_id>SMP0125712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Salla Disease/Infantile Sialic Acid Storage Disease</name>
      <smpdb_id>SMP0125714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tay-Sachs Disease</name>
      <smpdb_id>SMP0125715</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-3.9</value>
    </property>
  </experimental_properties>
  <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>
    <property>
      <kind>logp</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[(2R,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)[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@H](O)CO</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+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MBLBDJOUHNCFQT-LXGUWJNJSA-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>20.49</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>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7222922098&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00141</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>343911</pubchem_compound_id>
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  <chemspider_id/>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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</compound>
