Details of Metabolite

General Information of MET (ID: META00208)
Name N-Acetyl-D-glucosamine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
2 Acetamido 2 deoxy D glucose; 2 Acetamido 2 deoxyglucose; 2-(Acetylamino)-2-deoxyhexose; 2-Acetamido-2-deoxy-D-glucopyranose; 2-Acetamido-2-deoxy-D-glucose; 2-Acetamido-2-deoxyglucose; 2-Acetamido-D-glucose; 2-Acetylamino-2-deoxy-D-glucose; Acetylglucosamine; GlcNAc; N Acetyl D glucosamine; N-Acetylchitosamine; N-Acetylglucosamine; N-[(3R,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;Microbial
Structure Type   Carbohydrates and carbohydrate conjugates  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic oxygen compounds
Organooxygen compounds
Carbohydrates and carbohydrate conjugates
PubChem CID
439174
HMDB ID
HMDB0000215
Formula
C8H15NO6
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00140
ChEBI ID
506227
FooDB ID
FDB008032
ChemSpider ID
388319
METLIN ID
3356
Physicochemical Properties Molecular Weight 221.21 Topological Polar Surface Area 119
XlogP -1.7 Complexity 235
Heavy Atom Count 15 Rotatable Bond Count 2
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 6
Function
N-Acetyl-D-Glucosamine (N-acetlyglucosamine) is a monosaccharide derivative of glucose. Chemically it is an amide between glucosamine and acetic acid. A single N-acetlyglucosamine moiety linked to serine or threonine residues on nuclear and cytoplasmic proteins -O-GlcNAc, is an ubiquitous post-translational protein modification. O-GlcNAc modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly. O-GlcNAc regulates cellular responses to hormones such as insulin, initiates a protective response to stress, modulates a cell's capacity to grow and divide, and regulates gene transcription. In humans, it exists in skin, cartilage and blood vessel as a component of hyaluronic acid, and bone tissue, cornea and aorta as a component of keratan sulfate.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Alpha-N-acetylglucosaminidase (NAGLU) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of Naglu
                      Induced Change N-Acetyl-D-glucosamine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Lysosomal storage diseases [ICD-11: 5C56]
                      Details It is reported that knockout of Naglu leads to the decrease of N-acetyl-D-glucosamine levels compared with control group.
References
1 Near-Complete Correction of Profound Metabolomic Impairments Corresponding to Functional Benefit in MPS IIIB Mice after IV rAAV9-hNAGLU Gene Delivery. Mol Ther. 2017 Mar 1;25(3):792-802.

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