NP-MRD: Showing NP-Card for beta-N-Acetylglucosamine (NP0001176)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-19 23:58:52 UTC

NP-MRD ID

NP0001176

Secondary Accession Numbers

None

Natural Product 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>
NP0001176

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

221.2078 Da

Monoisotopic Mass

221.08994 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Arabidopsis thaliana	LOTUS Database	35616633
Averrhoa carambola	KNApSAcK Database	22123792
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000803

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1265441

References

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 ]
Kuk JH, Jung WJ, Jo GH, Kim YC, Kim KY, Park RD: Production of N-acetyl-beta-D-glucosamine from chitin by Aeromonas sp. GJ-18 crude enzyme. Appl Microbiol Biotechnol. 2005 Aug;68(3):384-9. doi: 10.1007/s00253-004-1877-y. Epub 2005 Feb 4. [PubMed:15692805 ]
Wu D, Zajonc DM, Fujio M, Sullivan BA, Kinjo Y, Kronenberg M, Wilson IA, Wong CH: Design of natural killer T cell activators: structure and function of a microbial glycosphingolipid bound to mouse CD1d. Proc Natl Acad Sci U S A. 2006 Mar 14;103(11):3972-7. doi: 10.1073/pnas.0600285103. Epub 2006 Mar 6. [PubMed:16537470 ]

Showing NP-Card for beta-N-Acetylglucosamine (NP0001176)

MOL for NP0001176 (beta-N-Acetylglucosamine)

3D MOL for NP0001176 (beta-N-Acetylglucosamine)

3D SDF for NP0001176 (beta-N-Acetylglucosamine)

3D-SDF for NP0001176 (beta-N-Acetylglucosamine)

PDB for NP0001176 (beta-N-Acetylglucosamine)

3D PDB for NP0001176 (beta-N-Acetylglucosamine)

SMILES for NP0001176 (beta-N-Acetylglucosamine)

INCHI for NP0001176 (beta-N-Acetylglucosamine)

Structure for NP0001176 (beta-N-Acetylglucosamine)

3D Structure for NP0001176 (beta-N-Acetylglucosamine)