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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-03-23 05:12:22 UTC
Update Date2017-12-07 21:25:19 UTC
HMDB IDHMDB0062641
Secondary Accession Numbers
  • HMDB62641
Metabolite Identification
Common NameAldehydo-N-acetyl-D-glucosamine
DescriptionAldehydo-N-acetyl-D-glucosamine, also known as 2-acetamido-2-Deoxy-D-glucose or D-GlcNAc, is classified as a member of the Hexoses. Hexoses are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Aldehydo-N-acetyl-D-glucosamine is considered to be soluble (in water) and acidic. Aldehydo-N-acetyl-D-glucosamine is a drug which is used for the treatment and prevention of osteoarthritis, by itself or in combination with chondroitin sulfate
Structure
Thumb
Synonyms
ValueSource
2-acetamido-2-Deoxy-D-glucoseChEBI
D-GlcNAcChEBI
N-AcetylchitosamineChEBI
N Acetyl D glucosamineMeSH
2 acetamido 2 Deoxy D glucoseMeSH
2 acetamido 2 DeoxyglucoseMeSH
2-acetamido-2-DeoxyglucoseMeSH
AcetylglucosamineMeSH
Chemical FormulaC8H15NO6
Average Molecular Weight221.2078
Monoisotopic Molecular Weight221.089937217
IUPAC NameN-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide
Traditional NameN acetylglucosamine
CAS Registry NumberNot Available
SMILES
[H]C(=O)[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@H](O)CO
InChI Identifier
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 KeyMBLBDJOUHNCFQT-LXGUWJNJSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Amino saccharide
  • Beta-hydroxy aldehyde
  • Acetamide
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Polyol
  • Aldehyde
  • Organonitrogen compound
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility148 g/lALOGPS
LogP-2.10ALOGPS
Predicted Properties
PropertyValueSource
logP-2.1ALOGPS
logP-3.9ChemAxon
logS-0.18ALOGPS
pKa (Strongest Acidic)11.56ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.09 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity48.45 m³·mol⁻¹ChemAxon
Polarizability20.49 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-0pvi-1931000000-fa145dffe949e1d8fc54View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-0lmr-2972000000-0672da151d0105b7b011View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-1000-2941000000-6e4ded528b518089efcbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9410000000-fde7b53bfdaa0df8ff8eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0ki6-4121900000-18b0ee1e133629444984View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-2790000000-c3f61bee76bc8ac4c91aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-9400000000-d8b548f3959cb7f090cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-9200000000-92b84dd993b3d248f4d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0c00-4920000000-e3a957b6dba9be60ab8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-9700000000-07eb56e1cdd8e2e22204View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9100000000-1798f1fad925afb90a46View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00141
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1738118
PDB IDNot Available
ChEBI ID17411
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available