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N-Acetylglucosamine (PC000474)

Record Information
Version1.0
Creation date2015-10-09 22:30:52 UTC
Update date2017-01-19 02:36:25 UTC
FoodComEx IDPC000474
FoodDB RecordFDB008032
Chemical Information
NameN-Acetylglucosamine
DescriptionMonomer of Chitinand is also in the exopolysaccharide from blue-green alga Cyanospira capsulata (CCD) N-Acetylglucosamine (N-acetyl-D-glucosamine, or GlcNAc, or NAG) is a monosaccharide derivative of glucose. It is part of a biopolymer in the bacterial cell wall, built from alternating units of GlcNAc and N-acetylmuramic acid (MurNAc), cross-linked with oligopeptides at the lactic acid residue of MurNAc. GlcNAc is the monomeric unit of the polymer chitin, which forms the outer coverings of insects and crustaceans. N-Acetylglucosamine is found in peach.
CAS Number7512-17-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-(Acetylamino)-2-deoxyglucose, 9CImanual
2-(acetylamino)-2-DeoxyhexoseHMDB
2-acetamido-2-Deoxy-D-glucopyranoseHMDB
2-acetamido-2-Deoxy-D-glucoseChEBI
2-acetamido-2-DeoxyglucoseHMDB
2-acetamido-D-GlucoseHMDB
2-acetylamino-2-Deoxy-D-glucoseHMDB
Acetylglucosaminemanual
GlcNAcChEBI
N-[(3R,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamideHMDB
N-Acetyl-D-glucosaminemanual
N-Acetylchitosaminemanual
N-Acetylglucosaminemanual
Chemical FormulaC8H15NO6
IUPAC nameN-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
InChI IdentifierInChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8?/m1/s1
InChI KeyOVRNDRQMDRJTHS-RTRLPJTCSA-N
Isomeric SMILESCC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
Average Molecular Weight221.2078
Monoisotopic Molecular Weight221.089937217
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Hexose monosaccharide
  • Monosaccharide
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointMp 205°CCD
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci J90835
AKSci K285
AKSci HMDB0000803
Cayman Chemical 13136
Glentham GC7987
MetaSci HMDB0000803
Toronto Research Chemicals A178000