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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-10-13 04:31:07 UTC

HMDB ID

HMDB0000803

Secondary Accession Numbers

HMDB00803

Metabolite Identification

Common Name

beta-N-Acetylglucosamine

Description

beta-N-Acetylglucosamine is an acylaminosugar, which is an organic compound containing a sugar linked to a chain through an N-acyl group. This compound is water-soluble. Glycosylation with beta-N-acetylglucosamine is one of the most common post-translational modifications. All animals and plants dynamically attach and remove beta-N-acetylglucosamine at serine and threonine residues on myriad nuclear and cytoplasmic proteins. beta-N-Acetylglucosamine cycling, which is tightly regulated by the concerted actions of two highly-conserved enzymes, serves as a nutrient and stress sensor. Proteins glycosylated with beta-N-acetylglucosamine can be found in almost every intracellular compartment and almost every functional class (PMID: 17460662 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000803
     RDKit          3D
beta-N-Acetylglucosamine
 30 30  0  0  0  0  0  0  0  0999 V2000
    3.8677    1.2576   -0.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989    0.3796    0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151   -0.2912    1.2407 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160    0.3272    0.0680 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947   -0.5349    0.8811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3694    0.2460    1.5061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4244   -0.6592    1.7022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781    1.1220    0.5128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3438    0.5050   -0.5544 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8591    0.7151   -0.4511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1650    2.0574   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0870   -0.9359   -0.7335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9709   -1.1952   -2.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1020   -1.5062   -0.0716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2221   -2.6334    0.7148 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2662    2.1513   -0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2681    0.7394   -1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7068    1.5935    0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2141    0.8937   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716   -1.0665    1.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0845    0.7420    2.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8405   -0.5696    2.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454    1.0810   -1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2478    0.1930    0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2914    0.2132   -1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7849    2.2383    0.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9866   -1.5434   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6973   -0.7564   -2.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946   -1.8613   -0.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827   -2.9024    1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  1
  6 21  1  1
  7 22  1  0
  9 23  1  6
 10 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  1
 13 28  1  0
 14 29  1  6
 15 30  1  0
M  END


  Mrv1652305271900042D          

 15 15  0  0  0  0            999 V2000
   -0.4363    1.0438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2776    0.6302    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9920    1.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1514    0.6323    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4387   -0.6062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4387   -1.4313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1526   -0.1927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8670   -0.6052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2764   -0.1948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8658    1.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5802    0.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9908   -0.6072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7053    0.6302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7053   -0.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198   -0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  2  1  0  0  0  0
  4  7  1  0  0  0  0
  7  5  1  0  0  0  0
  5  9  1  0  0  0  0
  9  2  1  0  0  0  0
  2  3  1  1  0  0  0
  4 10  1  1  0  0  0
  5  6  1  1  0  0  0
  7  8  1  6  0  0  0
  9 12  1  6  0  0  0
 10 11  1  0  0  0  0
 12 14  1  0  0  0  0
 14 13  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000803

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=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_KEY>
OVRNDRQMDRJTHS-FMDGEEDCSA-N

> <FORMULA>
C8H15NO6

> <MOLECULAR_WEIGHT>
221.2078

> <EXACT_MASS>
221.089937217

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.08480441489423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

> <ALOGPS_LOGP>
-2.60

> <JCHEM_LOGP>
-3.220574411666667

> <ALOGPS_LOGS>
0.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.811681816700894

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.604129514800414

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5720778168170417

> <JCHEM_POLAR_SURFACE_AREA>
119.25000000000001

> <JCHEM_REFRACTIVITY>
47.024699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetyl-D-glucosamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000803
     RDKit          3D
beta-N-Acetylglucosamine
 30 30  0  0  0  0  0  0  0  0999 V2000
    3.8677    1.2576   -0.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989    0.3796    0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151   -0.2912    1.2407 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160    0.3272    0.0680 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947   -0.5349    0.8811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3694    0.2460    1.5061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4244   -0.6592    1.7022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781    1.1220    0.5128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3438    0.5050   -0.5544 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8591    0.7151   -0.4511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1650    2.0574   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0870   -0.9359   -0.7335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9709   -1.1952   -2.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1020   -1.5062   -0.0716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2221   -2.6334    0.7148 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2662    2.1513   -0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2681    0.7394   -1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7068    1.5935    0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2141    0.8937   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716   -1.0665    1.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0845    0.7420    2.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8405   -0.5696    2.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454    1.0810   -1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2478    0.1930    0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2914    0.2132   -1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7849    2.2383    0.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9866   -1.5434   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6973   -0.7564   -2.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946   -1.8613   -0.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827   -2.9024    1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  1
  6 21  1  1
  7 22  1  0
  9 23  1  6
 10 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  1
 13 28  1  0
 14 29  1  6
 15 30  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      -0.814   1.948   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.518   1.176   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.852   1.946   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.149   1.180   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.819  -1.132   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.819  -2.672   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.152  -0.360   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.485  -1.130   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.516  -0.364   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.483   1.950   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.816   1.180   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       1.849  -1.133   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       3.183   1.176   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.183  -0.364   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.517  -1.133   0.000  0.00  0.00           C+0
CONECT    1    4    2                                                       
CONECT    2    1    9    3                                                  
CONECT    3    2                                                            
CONECT    4    1    7   10                                                  
CONECT    5    7    9    6                                                  
CONECT    6    5                                                            
CONECT    7    4    5    8                                                  
CONECT    8    7                                                            
CONECT    9    5    2   12                                                  
CONECT   10    4   11                                                       
CONECT   11   10                                                            
CONECT   12    9   14                                                       
CONECT   13   14                                                            
CONECT   14   12   13   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0000803
HETATM    1  C1  UNL     1       3.868   1.258  -0.486  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.999   0.380   0.334  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.515  -0.291   1.241  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.616   0.327   0.068  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.795  -0.535   0.881  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.369   0.246   1.506  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.424  -0.659   1.702  1.00  0.00           O  
HETATM    8  O3  UNL     1      -0.778   1.122   0.513  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.344   0.505  -0.554  1.00  0.00           C  
HETATM   10  C6  UNL     1      -2.859   0.715  -0.451  1.00  0.00           C  
HETATM   11  O4  UNL     1      -3.165   2.057  -0.466  1.00  0.00           O  
HETATM   12  C7  UNL     1      -1.087  -0.936  -0.734  1.00  0.00           C  
HETATM   13  O5  UNL     1      -0.971  -1.195  -2.121  1.00  0.00           O  
HETATM   14  C8  UNL     1       0.102  -1.506  -0.072  1.00  0.00           C  
HETATM   15  O6  UNL     1      -0.222  -2.633   0.715  1.00  0.00           O  
HETATM   16  H1  UNL     1       3.266   2.151  -0.771  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.268   0.739  -1.385  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.707   1.594   0.143  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.214   0.894  -0.689  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.372  -1.066   1.639  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.084   0.742   2.427  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.841  -0.570   2.590  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.045   1.081  -1.479  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.248   0.193   0.454  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.291   0.213  -1.335  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.785   2.238   0.292  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.987  -1.543  -0.421  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.697  -0.756  -2.631  1.00  0.00           H  
HETATM   29  H14 UNL     1       0.895  -1.861  -0.776  1.00  0.00           H  
HETATM   30  H15 UNL     1       0.583  -2.902   1.218  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5   19
CONECT    5    6   14   20
CONECT    6    7    8   21
CONECT    7   22
CONECT    8    9
CONECT    9   10   12   23
CONECT   10   11   24   25
CONECT   11   26
CONECT   12   13   14   27
CONECT   13   28
CONECT   14   15   29
CONECT   15   30
END

HMDB0000803
     RDKit          3D
beta-N-Acetylglucosamine
 30 30  0  0  0  0  0  0  0  0999 V2000
    3.8677    1.2576   -0.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989    0.3796    0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151   -0.2912    1.2407 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160    0.3272    0.0680 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947   -0.5349    0.8811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3694    0.2460    1.5061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4244   -0.6592    1.7022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781    1.1220    0.5128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3438    0.5050   -0.5544 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8591    0.7151   -0.4511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1650    2.0574   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0870   -0.9359   -0.7335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9709   -1.1952   -2.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1020   -1.5062   -0.0716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2221   -2.6334    0.7148 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2662    2.1513   -0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2681    0.7394   -1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7068    1.5935    0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2141    0.8937   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716   -1.0665    1.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0845    0.7420    2.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8405   -0.5696    2.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454    1.0810   -1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2478    0.1930    0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2914    0.2132   -1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7849    2.2383    0.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9866   -1.5434   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6973   -0.7564   -2.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946   -1.8613   -0.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827   -2.9024    1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  1
  6 21  1  1
  7 22  1  0
  9 23  1  6
 10 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  1
 13 28  1  0
 14 29  1  6
 15 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Acetamido-2-deoxy-D-glucose	ChEBI
2-Acetylamino-2-deoxy-D-glucose	ChEBI
Acetylglucosamine	ChEBI
BetaGlcNAc	ChEBI
GlcNAc-beta	ChEBI
N-Acetyl-D-glucosamine	ChEBI
N-Acetylglucosamine	ChEBI
WURCS=2.0/1,1,0/[a2122h-1b_1-5_2*ncc/3=o]/1/	ChEBI
GlcNAc-b	Generator
GlcNAc-β	Generator
b-N-Acetylglucosamine	Generator
Β-N-acetylglucosamine	Generator
N-Acetyl-b-D-glucosamine	HMDB
N-Acetyl-β-D-glucosamine	HMDB
N Acetyl D glucosamine	HMDB
2 Acetamido 2 deoxyglucose	HMDB
2 Acetamido 2 deoxy D glucose	HMDB
2-Acetamido-2-deoxyglucose	HMDB
2-Acetamido-2-deoxy-b-D-glucose	HMDB
2-Acetamido-2-deoxy-beta-D-glucose	HMDB
2-Acetamido-2-deoxy-beta-delta-glucose	HMDB
b-N-Acetyl-D-glucosamine	HMDB
beta-N-Acetyl-D-glucosamine	HMDB
beta-N-Acetyl-delta-glucosamine	HMDB
N-Acetyl-beta-D-glucosamine	HMDB
N-Acetyl glucosamine	HMDB

Chemical Formula

C₈H₁₅NO₆

Average Molecular Weight

221.2078

Monoisotopic Molecular Weight

221.089937217

IUPAC Name

N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

Traditional Name

N-acetyl-D-glucosamine

CAS Registry Number

14131-68-1

SMILES

CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=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 Key

OVRNDRQMDRJTHS-FMDGEEDCSA-N

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acetyl-D-glucosamine (CHEBI:28009 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)
Saliva (HMDB: HMDB0000803)

Excreta

Biofluid or Excreta

Feces (PMID: 24029555)
Urine (PMID: 32966057)

Cellular substructure

Cytoplasm (HMDB: HMDB0000803)

Source

Endogenous

Endogenous (HMDB: HMDB0000803)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	595.35 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-2.314 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	254 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.2	ChemAxon
logS	0.06	ALOGPS
pKa (Strongest Acidic)	11.6	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	21.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	150.566	31661259
DarkChem	[M-H]-	145.791	31661259
AllCCS	[M+H]+	149.735	32859911
AllCCS	[M-H]-	145.931	32859911
DeepCCS	[M+H]+	151.053	30932474
DeepCCS	[M-H]-	148.657	30932474
DeepCCS	[M-2H]-	182.93	30932474
DeepCCS	[M+Na]+	157.562	30932474
AllCCS	[M+H]+	149.7	32859911
AllCCS	[M+H-H2O]+	145.9	32859911
AllCCS	[M+NH4]+	153.3	32859911
AllCCS	[M+Na]+	154.3	32859911
AllCCS	[M-H]-	145.9	32859911
AllCCS	[M+Na-2H]-	146.4	32859911
AllCCS	[M+HCOO]-	147.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.57 minutes	32390414
Predicted by Siyang on May 30, 2022	9.5692 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.81 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	274.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	670.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	257.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	44.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	284.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	240.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	691.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	564.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	53.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	804.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	189.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	216.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	541.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	335.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	323.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-N-Acetylglucosamine	CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O	3657.7	Standard polar	33892256
beta-N-Acetylglucosamine	CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O	2082.8	Standard non polar	33892256
beta-N-Acetylglucosamine	CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O	2104.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
beta-N-Acetylglucosamine,1TMS,isomer #1	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O	1894.9	Semi standard non polar	33892256
beta-N-Acetylglucosamine,1TMS,isomer #2	CC(=O)N[C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	1900.1	Semi standard non polar	33892256
beta-N-Acetylglucosamine,1TMS,isomer #3	CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	1898.0	Semi standard non polar	33892256
beta-N-Acetylglucosamine,1TMS,isomer #4	CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	1908.2	Semi standard non polar	33892256
beta-N-Acetylglucosamine,1TMS,isomer #5	CC(=O)N([C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C	1835.0	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TMS,isomer #1	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	1915.8	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TMS,isomer #10	CC(=O)N([C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	1897.1	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TMS,isomer #2	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	1930.3	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TMS,isomer #3	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	1938.6	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TMS,isomer #4	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C	1890.6	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TMS,isomer #5	CC(=O)N[C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	1939.6	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TMS,isomer #6	CC(=O)N[C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	1939.6	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TMS,isomer #7	CC(=O)N([C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C	1911.9	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TMS,isomer #8	CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1933.2	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TMS,isomer #9	CC(=O)N([C@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	1895.9	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TMS,isomer #1	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	2003.5	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TMS,isomer #10	CC(=O)N([C@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	1967.8	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TMS,isomer #2	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	2011.5	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TMS,isomer #3	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C	1939.5	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TMS,isomer #4	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2016.7	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TMS,isomer #5	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	1961.8	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TMS,isomer #6	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	1981.0	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TMS,isomer #7	CC(=O)N[C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2006.4	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TMS,isomer #8	CC(=O)N([C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	1967.9	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TMS,isomer #9	CC(=O)N([C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	1970.5	Semi standard non polar	33892256
beta-N-Acetylglucosamine,4TMS,isomer #1	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2036.2	Semi standard non polar	33892256
beta-N-Acetylglucosamine,4TMS,isomer #2	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	2024.8	Semi standard non polar	33892256
beta-N-Acetylglucosamine,4TMS,isomer #3	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2040.9	Semi standard non polar	33892256
beta-N-Acetylglucosamine,4TMS,isomer #4	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2039.6	Semi standard non polar	33892256
beta-N-Acetylglucosamine,4TMS,isomer #5	CC(=O)N([C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2031.3	Semi standard non polar	33892256
beta-N-Acetylglucosamine,5TMS,isomer #1	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2092.3	Semi standard non polar	33892256
beta-N-Acetylglucosamine,5TMS,isomer #1	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2154.1	Standard non polar	33892256
beta-N-Acetylglucosamine,5TMS,isomer #1	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2100.6	Standard polar	33892256
beta-N-Acetylglucosamine,1TBDMS,isomer #1	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O	2151.2	Semi standard non polar	33892256
beta-N-Acetylglucosamine,1TBDMS,isomer #2	CC(=O)N[C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	2148.3	Semi standard non polar	33892256
beta-N-Acetylglucosamine,1TBDMS,isomer #3	CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2164.7	Semi standard non polar	33892256
beta-N-Acetylglucosamine,1TBDMS,isomer #4	CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2166.9	Semi standard non polar	33892256
beta-N-Acetylglucosamine,1TBDMS,isomer #5	CC(=O)N([C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C	2109.9	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TBDMS,isomer #1	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	2423.5	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TBDMS,isomer #10	CC(=O)N([C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2384.2	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TBDMS,isomer #2	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2439.8	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TBDMS,isomer #3	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2433.2	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TBDMS,isomer #4	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C	2371.0	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TBDMS,isomer #5	CC(=O)N[C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2427.0	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TBDMS,isomer #6	CC(=O)N[C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2436.0	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TBDMS,isomer #7	CC(=O)N([C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C	2406.0	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TBDMS,isomer #8	CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2423.5	Semi standard non polar	33892256
beta-N-Acetylglucosamine,2TBDMS,isomer #9	CC(=O)N([C@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C	2389.3	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TBDMS,isomer #1	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2686.1	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TBDMS,isomer #10	CC(=O)N([C@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2624.3	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TBDMS,isomer #2	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2664.9	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TBDMS,isomer #3	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C	2622.2	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TBDMS,isomer #4	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2659.1	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TBDMS,isomer #5	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C	2629.1	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TBDMS,isomer #6	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2628.6	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TBDMS,isomer #7	CC(=O)N[C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2682.8	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TBDMS,isomer #8	CC(=O)N([C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C	2658.8	Semi standard non polar	33892256
beta-N-Acetylglucosamine,3TBDMS,isomer #9	CC(=O)N([C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2650.9	Semi standard non polar	33892256
beta-N-Acetylglucosamine,4TBDMS,isomer #1	CC(=O)N[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2872.7	Semi standard non polar	33892256
beta-N-Acetylglucosamine,4TBDMS,isomer #2	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C	2860.6	Semi standard non polar	33892256
beta-N-Acetylglucosamine,4TBDMS,isomer #3	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2859.4	Semi standard non polar	33892256
beta-N-Acetylglucosamine,4TBDMS,isomer #4	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2849.9	Semi standard non polar	33892256
beta-N-Acetylglucosamine,4TBDMS,isomer #5	CC(=O)N([C@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2868.3	Semi standard non polar	33892256
beta-N-Acetylglucosamine,5TBDMS,isomer #1	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3101.4	Semi standard non polar	33892256
beta-N-Acetylglucosamine,5TBDMS,isomer #1	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3050.3	Standard non polar	33892256
beta-N-Acetylglucosamine,5TBDMS,isomer #1	CC(=O)N([C@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2705.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ue9-6920000000-c07df80c6fb758af9cd2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (4 TMS) - 70eV, Positive	splash10-0007-3331900000-c6fab10d67507eecce65	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-N-Acetylglucosamine GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-N-Acetylglucosamine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0f79-0950000000-61c83c523f164fae3cc7	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-N-Acetylglucosamine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-001a-9700000000-ea1c503f19d4401abae9	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-N-Acetylglucosamine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-053v-9000000000-e3255df1a993bd7f2b8d	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-N-Acetylglucosamine 10V, Positive-QTOF	splash10-00di-0390000000-ce54c5d356ec2fc8ab9f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-N-Acetylglucosamine 20V, Positive-QTOF	splash10-0ik9-2940000000-f88941018e49a26c37be	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-N-Acetylglucosamine 40V, Positive-QTOF	splash10-01ox-9400000000-ebc784f7cee5c3483d94	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-N-Acetylglucosamine 10V, Negative-QTOF	splash10-05g0-8920000000-5889786c5b50003455d6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-N-Acetylglucosamine 20V, Negative-QTOF	splash10-0pb9-9820000000-15d2a7694c2cca4aa77e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-N-Acetylglucosamine 40V, Negative-QTOF	splash10-0a4i-9100000000-69f7eb5167a70a24f71a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-N-Acetylglucosamine 10V, Negative-QTOF	splash10-0a4i-9500000000-2c2b09cb6bfb29039085	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-N-Acetylglucosamine 20V, Negative-QTOF	splash10-0abc-9540000000-a1f7d557237a521d306a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-N-Acetylglucosamine 40V, Negative-QTOF	splash10-0a4i-9000000000-18eabe9e3d3657888360	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-N-Acetylglucosamine 10V, Positive-QTOF	splash10-0udi-0390000000-3820a7eec5a8c72f49d9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-N-Acetylglucosamine 20V, Positive-QTOF	splash10-0h90-9740000000-db880363194a3979c637	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-N-Acetylglucosamine 40V, Positive-QTOF	splash10-0229-9200000000-cdcf015aa799dc7d6d8b	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5767

PubChem Compound

24139

PDB ID

Not Available

ChEBI ID

28009

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1265441

References

Synthesis Reference

Kuk, J. H.; Jung, W. J.; Jo, G. H.; Kim, Y. C.; Kim, K. Y.; Park, R. D. Production of N-acetyl-b-D-glucosamine from chitin by Aeromonas sp. GJ-18 crude enzyme. Applied Microbiology and Biotechnology (2005), 68(3), 384-389.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Yao AY, Tang HY, Wang Y, Feng MF, Zhou RL: Inhibition of the activating signals in NK92 cells by recombinant GST-sHLA-G1a chain. Cell Res. 2004 Apr;14(2):155-60. [PubMed:15115617 ]
Kum K, Khanna R, Vinayak VK: Characterization of surface associated antigens of axenic Giardia lamblia trophozoites & their recognition by human sera. Indian J Med Res. 1991 Jan;93:40-6. [PubMed:2022401 ]
Hart GW, Housley MP, Slawson C: Cycling of O-linked beta-N-acetylglucosamine on nucleocytoplasmic proteins. Nature. 2007 Apr 26;446(7139):1017-22. [PubMed:17460662 ]

Showing metabocard for beta-N-Acetylglucosamine (HMDB0000803)

MOL for HMDB0000803 (beta-N-Acetylglucosamine)

3D MOL for HMDB0000803 (beta-N-Acetylglucosamine)

3D SDF for HMDB0000803 (beta-N-Acetylglucosamine)

3D-SDF for HMDB0000803 (beta-N-Acetylglucosamine)

PDB for HMDB0000803 (beta-N-Acetylglucosamine)

3D PDB for HMDB0000803 (beta-N-Acetylglucosamine)

SMILES for HMDB0000803 (beta-N-Acetylglucosamine)

INCHI for HMDB0000803 (beta-N-Acetylglucosamine)

Structure for HMDB0000803 (beta-N-Acetylglucosamine)

3D Structure for HMDB0000803 (beta-N-Acetylglucosamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra