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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:48:59 UTC

HMDB ID

HMDB0000215

Secondary Accession Numbers

HMDB0000533
HMDB0014288
HMDB00215
HMDB00533
HMDB14288

Metabolite Identification

Common Name

N-Acetyl-D-glucosamine

Description

N-Acetyl-D-glucosamine, also known as glcnac or N-acetylchitosamine, 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. O-N-Acetyl-D-glucosamine 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. N-Acetyl-D-glucosamine is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-D-glucosamine exists in all living organisms, ranging from bacteria to humans. 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. Within humans, N-acetyl-D-glucosamine participates in a number of enzymatic reactions. In particular, N-acetyl-D-glucosamine can be biosynthesized from chitobiose through the action of the enzyme Beta-hexosaminidase subunit alpha. In addition, N-acetyl-D-glucosamine can be biosynthesized from chitin through the action of the enzyme chitotriosidase-1. O-N-Acetyl-D-glucosamine modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly. In humans, N-acetyl-D-glucosamine is involved in the metabolic disorder called the salla disease/infantile sialic acid storage disease pathway. Outside of the human body, N-Acetyl-D-glucosamine is found, on average, in the highest concentration within milk (cow). N-Acetyl-D-glucosamine has also been detected, but not quantified in, peachs. This could make N-acetyl-D-glucosamine a potential biomarker for the consumption of these foods. Chemically it is an amide between glucosamine and acetic acid. N-Acetyl-D-Glucosamine (N-acetlyglucosamine) is a monosaccharide derivative of glucose. 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.

Structure

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

HMDB0000215
     RDKit          3D
N-Acetyl-D-glucosamine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.4789   -0.6168    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0416   -0.6999    0.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489   -1.3372    1.6685 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0133   -0.0914   -0.1245 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6536   -0.2179    0.3144 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1290    1.2014    0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2532    1.9581   -0.5870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2010    1.1910    0.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0291    0.6401   -0.0297 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4608    0.8096    0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7356    2.1656    0.5761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6430   -0.8171   -0.1508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5341   -1.5471   -0.9112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2442   -0.8207   -0.7396 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1614   -2.0873   -1.1260 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9352    0.3528    0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5579   -0.7601   -0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0561   -1.4107    0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2658    0.4381   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5795   -0.8031    1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.5939    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1732    2.3083   -0.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8641    1.1049   -1.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6116    0.3282    1.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1777    0.3708   -0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147    2.7301   -0.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532   -1.2122    0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8958   -2.2722   -0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1918   -0.1545   -1.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4054   -2.3449   -1.8971 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  0
  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

  Mrv0541 04141315482D          

 15 15  0  0  0  0            999 V2000
   11.5795   -7.4839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8650   -7.8964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8650   -8.7214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5795   -9.1339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2939   -8.7214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2939   -7.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0084   -7.4839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0084   -9.1339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1505   -9.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5795   -9.9589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1505   -7.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1505   -6.6589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0084   -9.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2939  -10.3714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7229  -10.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  6  0  0  0
  3  9  1  6  0  0  0
  4 10  1  1  0  0  0
  2 11  1  1  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000215

> <DATABASE_NAME>
hmdb

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

> <FORMULA>
C8H15NO6

> <MOLECULAR_WEIGHT>
221.2078

> <EXACT_MASS>
221.089937217

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
20.558453591969588

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(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>
12.811681816701025

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.604129514800583

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7815744979932174

> <JCHEM_POLAR_SURFACE_AREA>
119.25

> <JCHEM_REFRACTIVITY>
47.024699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
GlcNAc

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000215
     RDKit          3D
N-Acetyl-D-glucosamine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.4789   -0.6168    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0416   -0.6999    0.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489   -1.3372    1.6685 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0133   -0.0914   -0.1245 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6536   -0.2179    0.3144 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1290    1.2014    0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2532    1.9581   -0.5870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2010    1.1910    0.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0291    0.6401   -0.0297 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4608    0.8096    0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7356    2.1656    0.5761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6430   -0.8171   -0.1508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5341   -1.5471   -0.9112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2442   -0.8207   -0.7396 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1614   -2.0873   -1.1260 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9352    0.3528    0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5579   -0.7601   -0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0561   -1.4107    0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2658    0.4381   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5795   -0.8031    1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.5939    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1732    2.3083   -0.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8641    1.1049   -1.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6116    0.3282    1.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1777    0.3708   -0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147    2.7301   -0.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532   -1.2122    0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8958   -2.2722   -0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1918   -0.1545   -1.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4054   -2.3449   -1.8971 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  0
  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                                 14-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-APR-13         0                                  
HETATM    1  O   UNK     0      21.615 -13.970   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      20.281 -14.740   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.281 -16.280   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.615 -17.050   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.949 -16.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.949 -14.740   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      24.282 -13.970   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      24.282 -17.050   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      18.948 -17.050   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      21.615 -18.590   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      18.948 -13.970   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      18.948 -12.430   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      24.282 -18.590   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      22.949 -19.360   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      25.616 -19.360   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5   13                                                       
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    2   12                                                       
CONECT   12   11                                                            
CONECT   13    8   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0000215
HETATM    1  C1  UNL     1       4.479  -0.617   0.246  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.042  -0.700   0.631  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.749  -1.337   1.668  1.00  0.00           O  
HETATM    4  N1  UNL     1       2.013  -0.091  -0.124  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.654  -0.218   0.314  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.129   1.201   0.563  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.253   1.958  -0.587  1.00  0.00           O  
HETATM    8  O3  UNL     1      -1.201   1.191   0.956  1.00  0.00           O  
HETATM    9  C5  UNL     1      -2.029   0.640  -0.030  1.00  0.00           C  
HETATM   10  C6  UNL     1      -3.461   0.810   0.417  1.00  0.00           C  
HETATM   11  O4  UNL     1      -3.736   2.166   0.576  1.00  0.00           O  
HETATM   12  C7  UNL     1      -1.643  -0.817  -0.151  1.00  0.00           C  
HETATM   13  O5  UNL     1      -2.534  -1.547  -0.911  1.00  0.00           O  
HETATM   14  C8  UNL     1      -0.244  -0.821  -0.740  1.00  0.00           C  
HETATM   15  O6  UNL     1       0.161  -2.087  -1.126  1.00  0.00           O  
HETATM   16  H1  UNL     1       4.935   0.353   0.511  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.558  -0.760  -0.856  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.056  -1.411   0.734  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.266   0.438  -0.988  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.579  -0.803   1.232  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.714   1.594   1.420  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.173   2.308  -0.712  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.864   1.105  -1.014  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.612   0.328   1.400  1.00  0.00           H  
HETATM   25  H10 UNL     1      -4.178   0.371  -0.287  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.215   2.730  -0.059  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.553  -1.212   0.894  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.896  -2.272  -0.326  1.00  0.00           H  
HETATM   29  H14 UNL     1      -0.192  -0.154  -1.632  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.405  -2.345  -1.897  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

HMDB0000215
     RDKit          3D
N-Acetyl-D-glucosamine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.4789   -0.6168    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0416   -0.6999    0.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489   -1.3372    1.6685 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0133   -0.0914   -0.1245 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6536   -0.2179    0.3144 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1290    1.2014    0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2532    1.9581   -0.5870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2010    1.1910    0.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0291    0.6401   -0.0297 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4608    0.8096    0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7356    2.1656    0.5761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6430   -0.8171   -0.1508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5341   -1.5471   -0.9112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2442   -0.8207   -0.7396 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1614   -2.0873   -1.1260 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9352    0.3528    0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5579   -0.7601   -0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0561   -1.4107    0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2658    0.4381   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5795   -0.8031    1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.5939    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1732    2.3083   -0.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8641    1.1049   -1.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6116    0.3282    1.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1777    0.3708   -0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147    2.7301   -0.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532   -1.2122    0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8958   -2.2722   -0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1918   -0.1545   -1.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4054   -2.3449   -1.8971 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  0
  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
GlcNAc	ChEBI
N-Acetylchitosamine	ChEBI
2-(Acetylamino)-2-deoxyhexose	HMDB
2-Acetamido-2-deoxy-D-glucopyranose	HMDB
2-Acetamido-2-deoxyglucose	HMDB
2-Acetamido-D-glucose	HMDB
2-Acetylamino-2-deoxy-D-glucose	HMDB
Acetylglucosamine	HMDB
N-Acetylglucosamine	HMDB
N-[(3R,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide	HMDB
2 Acetamido 2 deoxyglucose	HMDB
N Acetyl D glucosamine	HMDB
2 Acetamido 2 deoxy D glucose	HMDB

Chemical Formula

C₈H₁₅NO₆

Average Molecular Weight

221.2078

Monoisotopic Molecular Weight

221.089937217

IUPAC Name

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

Traditional Name

GlcNAc

CAS Registry Number

7512-17-6

SMILES

CC(=O)N[C@H]1C(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-RTRLPJTCSA-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-acetylglucosamine (CHEBI:506227 )
Amino sugars (C00140 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Cellular substructure

Organelle

Lysosome (HMDB: HMDB0000215)

Organ

Cell

Neuron (HMDB: HMDB0000215)

Hematocyte

Platelet (HMDB: HMDB0000215)

Excreta

Biofluid or Excreta

Urine (PMID: 2026685)
Feces (PMID: 20669995)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000215)

Source

Endogenous

Endogenous (HMDB: HMDB0000215)

Plant

Plant (HMDB: HMDB0000215)

Exogenous

Food

Food (HMDB: HMDB0000215)

Animal origin

Poultry

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)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Fruit

Drupe

Peach (FooDB: FOOD00149)

Exogenous (HMDB: HMDB0000215)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Amino Sugar Metabolism (HMDB: HMDB0000215)
Amino Sugar Metabolism (PathBank: SMP0063580)
Amino Sugar and Nucleotide Sugar Metabolism III (PathBank: SMP0121303)
1,6-Anhydro-N-acetylmuramic Acid Recycling (PathBank: SMP0122240)
Inner Membrane Transport (PathBank: SMP0121270)
Amino Sugar and Nucleotide Sugar Metabolism I (PathBank: SMP0121302)
Amino Sugar and Nucleotide Sugar Metabolism II (PathBank: SMP0000906)

Disease pathway

Salla Disease/Infantile Sialic Acid Storage Disease (PathBank: SMP0120524)
G(M2)-Gangliosidosis: Variant B, Tay-Sachs Disease (PathBank: SMP0120599)
Sialuria or French Type Sialuria (PathBank: SMP0000216)
Tay-Sachs Disease (PathBank: SMP0120545)

Role

Industrial application

Food and nutrition

Nutritional supplement (HMDB: HMDB0000215)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	167 mg/mL	Not Available
LogP	-2.1	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Astarita_neg	142.7	30932474
[M+H]+	MetCCS_test_pos	147.29	30932474
[M-H]-	Not Available	153.7	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002012

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)	-0.78	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	20.56 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]+	151.016	31661259
DarkChem	[M-H]-	145.319	31661259
AllCCS	[M+H]+	150.007	32859911
AllCCS	[M-H]-	146.244	32859911
DeepCCS	[M+H]+	149.284	30932474
DeepCCS	[M-H]-	146.888	30932474
DeepCCS	[M-2H]-	181.186	30932474
DeepCCS	[M+Na]+	155.964	30932474
AllCCS	[M+H]+	150.0	32859911
AllCCS	[M+H-H2O]+	146.3	32859911
AllCCS	[M+NH4]+	153.5	32859911
AllCCS	[M+Na]+	154.5	32859911
AllCCS	[M-H]-	146.2	32859911
AllCCS	[M+Na-2H]-	146.8	32859911
AllCCS	[M+HCOO]-	147.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-D-glucosamine	CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O	3681.1	Standard polar	33892256
N-Acetyl-D-glucosamine	CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O	2002.4	Standard non polar	33892256
N-Acetyl-D-glucosamine	CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O	2115.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-D-glucosamine,1TMS,isomer #1	CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O	1917.8	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,1TMS,isomer #2	CC(=O)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	1928.6	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,1TMS,isomer #3	CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	1918.6	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,1TMS,isomer #4	CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	1920.9	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,1TMS,isomer #5	CC(=O)N([C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C	1860.6	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TMS,isomer #1	CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	1940.3	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TMS,isomer #10	CC(=O)N([C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	1912.2	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TMS,isomer #2	CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	1941.2	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TMS,isomer #3	CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	1939.2	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TMS,isomer #4	CC(=O)N([C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C	1932.8	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TMS,isomer #5	CC(=O)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	1963.6	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TMS,isomer #6	CC(=O)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	1968.2	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TMS,isomer #7	CC(=O)N([C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C	1935.2	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TMS,isomer #8	CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1959.5	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TMS,isomer #9	CC(=O)N([C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	1914.9	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TMS,isomer #1	CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	2002.1	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TMS,isomer #10	CC(=O)N([C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	1974.7	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TMS,isomer #2	CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	2016.3	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TMS,isomer #3	CC(=O)N([C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C	1972.4	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TMS,isomer #4	CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2010.6	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TMS,isomer #5	CC(=O)N([C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	1983.3	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TMS,isomer #6	CC(=O)N([C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	1997.5	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TMS,isomer #7	CC(=O)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2026.9	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TMS,isomer #8	CC(=O)N([C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	1980.4	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TMS,isomer #9	CC(=O)N([C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	1975.4	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,4TMS,isomer #1	CC(=O)N[C@H]1C(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	2037.2	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,4TMS,isomer #2	CC(=O)N([C@H]1C(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	2042.1	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,4TMS,isomer #3	CC(=O)N([C@H]1C(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	2048.3	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,4TMS,isomer #4	CC(=O)N([C@H]1C(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	2047.9	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,4TMS,isomer #5	CC(=O)N([C@H]1C(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	2040.3	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,5TMS,isomer #1	CC(=O)N([C@H]1C(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	2091.8	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,5TMS,isomer #1	CC(=O)N([C@H]1C(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	2155.6	Standard non polar	33892256
N-Acetyl-D-glucosamine,5TMS,isomer #1	CC(=O)N([C@H]1C(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	2099.0	Standard polar	33892256
N-Acetyl-D-glucosamine,1TBDMS,isomer #1	CC(=O)N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O	2175.9	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,1TBDMS,isomer #2	CC(=O)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	2176.2	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,1TBDMS,isomer #3	CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2179.1	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,1TBDMS,isomer #4	CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2182.6	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,1TBDMS,isomer #5	CC(=O)N([C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C	2137.2	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #1	CC(=O)N[C@H]1C(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	2419.4	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #10	CC(=O)N([C@H]1C(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	2386.0	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #2	CC(=O)N[C@H]1C(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	2438.0	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #3	CC(=O)N[C@H]1C(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	2432.6	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #4	CC(=O)N([C@H]1C(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	2396.2	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #5	CC(=O)N[C@H]1C(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	2435.0	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #6	CC(=O)N[C@H]1C(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	2452.0	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #7	CC(=O)N([C@H]1C(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	2414.8	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #8	CC(=O)N[C@H]1C(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	2433.0	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #9	CC(=O)N([C@H]1C(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	2398.4	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #1	CC(=O)N[C@H]1C(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
N-Acetyl-D-glucosamine,3TBDMS,isomer #10	CC(=O)N([C@H]1C(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	2631.3	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #2	CC(=O)N[C@H]1C(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	2672.0	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #3	CC(=O)N([C@H]1C(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	2631.3	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #4	CC(=O)N[C@H]1C(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	2662.6	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #5	CC(=O)N([C@H]1C(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	2643.3	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #6	CC(=O)N([C@H]1C(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	2634.5	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #7	CC(=O)N[C@H]1C(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	2695.3	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #8	CC(=O)N([C@H]1C(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	2657.1	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #9	CC(=O)N([C@H]1C(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	2648.6	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,4TBDMS,isomer #1	CC(=O)N[C@H]1C(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	2889.4	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,4TBDMS,isomer #2	CC(=O)N([C@H]1C(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	2867.7	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,4TBDMS,isomer #3	CC(=O)N([C@H]1C(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	2860.1	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,4TBDMS,isomer #4	CC(=O)N([C@H]1C(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	2853.3	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,4TBDMS,isomer #5	CC(=O)N([C@H]1C(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	2865.7	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,5TBDMS,isomer #1	CC(=O)N([C@H]1C(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	3094.3	Semi standard non polar	33892256
N-Acetyl-D-glucosamine,5TBDMS,isomer #1	CC(=O)N([C@H]1C(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	3054.5	Standard non polar	33892256
N-Acetyl-D-glucosamine,5TBDMS,isomer #1	CC(=O)N([C@H]1C(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	2695.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)	splash10-0ktb-1931000000-1c4cb4ec9b01c3571b7d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)	splash10-0ktb-0931000000-943fefe13d3449a92db7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)	splash10-0f9j-1930000000-388fd70c48f209a58653	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)	splash10-00di-9620000000-1fd16b8e8608db3ef657	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)	splash10-00di-9620000000-ceed8b621b338130ce76	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)	splash10-00di-9620000000-8a3ade37d256b2bd4585	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)	splash10-0ktb-1931000000-1c4cb4ec9b01c3571b7d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)	splash10-0ktb-0931000000-943fefe13d3449a92db7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)	splash10-0f9j-1930000000-388fd70c48f209a58653	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)	splash10-00di-9620000000-1fd16b8e8608db3ef657	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)	splash10-00di-9620000000-ceed8b621b338130ce76	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)	splash10-00di-9620000000-8a3ade37d256b2bd4585	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ue9-6920000000-c07df80c6fb758af9cd2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (4 TMS) - 70eV, Positive	splash10-0007-3332900000-ee533266929b5b95ee4d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 10V, Negative-QTOF	splash10-0pb9-9800000000-d2628c9d8baf55923bf5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 35V, Negative-QTOF	splash10-0pb9-9500000000-76ab0b7c683cc252741d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 35V, Negative-QTOF	splash10-0pb9-9400000000-5b6f61c6f220e75c6736	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 35V, Negative-QTOF	splash10-0pb9-9500000000-17fd92d5a45dc38915af	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 40V, Negative-QTOF	splash10-0a4i-9300000000-ccb575a1c77c8addd5fe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 35V, Negative-QTOF	splash10-0pb9-9500000000-bf8c7a4f84891bcf3eb2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 35V, Negative-QTOF	splash10-0a4i-9000000000-f38ecd220da0924d093c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 20V, Negative-QTOF	splash10-0ab9-9400000000-eaa89be4aad99c7a4503	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 35V, Positive-QTOF	splash10-000i-3900000000-819a6ad0f73785d9287c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 10V, Positive-QTOF	splash10-000i-1910000000-723db02c59f390b489a7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 40V, Positive-QTOF	splash10-0537-9000000000-735f54db3223e736c337	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 20V, Positive-QTOF	splash10-003e-9600000000-197c8bc76e52b96b9871	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 10V, Positive-QTOF	splash10-00di-1490000000-40dfe33adabe6ad7a7a8	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 20V, Positive-QTOF	splash10-0il0-2940000000-880c7b1fb58ed63f0ee2	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 40V, Positive-QTOF	splash10-01ox-9400000000-e1f07558d7921e9f24e1	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 10V, Negative-QTOF	splash10-05g0-8920000000-d504941e0508d1593f33	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 20V, Negative-QTOF	splash10-0pb9-9820000000-753556be259b7e745ba7	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 40V, Negative-QTOF	splash10-0a4i-9100000000-bad102d081eb3bbc006b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 10V, Negative-QTOF	splash10-0a4i-9500000000-2c2b09cb6bfb29039085	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 20V, Negative-QTOF	splash10-0abc-9540000000-a1f7d557237a521d306a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 40V, Negative-QTOF	splash10-0a4i-9000000000-18eabe9e3d3657888360	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 10V, Positive-QTOF	splash10-0udi-0390000000-3820a7eec5a8c72f49d9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 20V, Positive-QTOF	splash10-0h90-9740000000-db880363194a3979c637	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 40V, Positive-QTOF	splash10-0229-9200000000-cdcf015aa799dc7d6d8b	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane
Lysosome

Biospecimen Locations

Blood
Breast Milk
Feces
Saliva
Urine

Tissue Locations

Intestine
Neuron
Placenta
Platelet
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Amino Sugar Metabolism
Sialuria or French Type Sialuria		Not Available
Salla Disease/Infantile Sialic Acid Storage Disease		Not Available
Tay-Sachs Disease		Not Available
G(M2)-Gangliosidosis: Variant B, Tay-sachs disease		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Breast Milk	Detected and Quantified	204.3278984 uM	Adult (>18 years old)	Female	Normal	11787731	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	27622378	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	2.23 +/- 1.83 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	2.40 +/- 2.35 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	21.4 +/- 18.6 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	3.14 +/- 2.38 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	3.78 +/- 3.93 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	4.41 +/- 5.98 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Urine	Detected and Quantified	2.96 +/- 1.85 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	2026685	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	asymptomatic diverticulosis	27622378	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	symptomatic uncomplicated diverticular disease	27622378	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Diverticular disease
Tursi A, Mastromarino P, Capobianco D, Elisei W, Miccheli A, Capuani G, Tomassini A, Campagna G, Picchio M, Giorgetti G, Fabiocchi F, Brandimarte G: Assessment of Fecal Microbiota and Fecal Metabolome in Symptomatic Uncomplicated Diverticular Disease of the Colon. J Clin Gastroenterol. 2016 Oct;50 Suppl 1:S9-S12. doi: 10.1097/MCG.0000000000000626. [PubMed:27622378 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008032

KNApSAcK ID

Not Available

Chemspider ID

388319

KEGG Compound ID

C00140

BioCyc ID

Not Available

BiGG ID

34006

Wikipedia Link

Not Available

METLIN ID

3356

PubChem Compound

439174

PDB ID

Not Available

ChEBI ID

506227

Food Biomarker Ontology

Not Available

VMH ID

ACGAM

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Zhang, He; Qi, Shanlong; Yang, Shenggui. Production of N-acetyl-D-glucosamine from chitin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 6pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Nakagawa F, Schulte BA, Spicer SS: Lectin cytochemical evaluation of somatosensory neurons and their peripheral and central processes in rat and man. Cell Tissue Res. 1986;245(3):579-89. [PubMed:3757018 ]
Hatcher VB, Schwarzmann GO, Jeanloz RW, McArthur JW: Changes in the sialic acid concentration in the major cervical glycoprotein from the bonnet monkey (Macaca radiata) during a hormonally induced cycle. Fertil Steril. 1977 Jun;28(6):682-8. [PubMed:405259 ]
Percheron F: [Beta-D-mannosidase]. Bull Acad Natl Med. 1995 May;179(5):881-91; discussion 892. [PubMed:7583460 ]
Collard CD, Montalto MC, Reenstra WR, Buras JA, Stahl GL: Endothelial oxidative stress activates the lectin complement pathway: role of cytokeratin 1. Am J Pathol. 2001 Sep;159(3):1045-54. [PubMed:11549596 ]
Mollicone R, Candelier JJ, Mennesson B, Couillin P, Venot AP, Oriol R: Five specificity patterns of (1----3)-alpha-L-fucosyltransferase activity defined by use of synthetic oligosaccharide acceptors. Differential expression of the enzymes during human embryonic development and in adult tissues. Carbohydr Res. 1992 Apr 10;228(1):265-76. [PubMed:1366057 ]
Kottgen E, Hell B, Muller C, Kainer F, Tauber R: Developmental changes in the glycosylation and binding properties of human fibronectins. Characterization of the glycan structures and ligand binding of human fibronectins from adult plasma, cord blood and amniotic fluid. Biol Chem Hoppe Seyler. 1989 Dec;370(12):1285-94. [PubMed:2619923 ]
Madrid JF, Castells MT, Martinez-Menarguez JA, Aviles M, Hernandez F, Ballesta J: Subcellular characterization of glycoproteins in the principal cells of human gallbladder. A lectin cytochemical study. Histochemistry. 1994 Mar;101(3):195-204. [PubMed:8056619 ]
Weiner B, Fischer T, Waxman S: Hemostasis in the era of the chronic anticoagulated patient. J Invasive Cardiol. 2003 Nov;15(11):669-73; quiz 674. [PubMed:14608143 ]
Yates AD, Watkins WM: Enzymes involved in the biosynthesis of glycoconjugates. A UDP-2-acetamido-2-deoxy-D-glucose: beta-D-galactopyranosyl-(1 leads to 4)-saccharide (1 leads to 3)-2-acetamido-2-deoxy-beta-D- glucopyranosyltransferase in human serum. Carbohydr Res. 1983 Aug 16;120:251-68. [PubMed:6226355 ]
Slawson C, Housley MP, Hart GW: O-GlcNAc cycling: how a single sugar post-translational modification is changing the way we think about signaling networks. J Cell Biochem. 2006 Jan 1;97(1):71-83. [PubMed:16237703 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 23 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase

General function:: Involved in ATP binding
Specific function:: Regulates and initiates biosynthesis of N-acetylneuraminic acid (NeuAc), a precursor of sialic acids. Plays an essential role in early development (By similarity). Required for normal sialylation in hematopoietic cells. Sialylation is implicated in cell adhesion, signal transduction, tumorigenicity and metastatic behavior of malignant cells.
Gene Name:: GNE
Uniprot ID:: Q9Y223
Molecular weight:: 83065.25

Enzyme Details

2. N-acylglucosamine 2-epimerase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the interconversion of N-acetylglucosamine to N-acetylmannosamine. Binds to renin forming a protein complex called high molecular weight (HMW) renin and inhibits renin activity. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway: although human is not able to catalyze formation of Neu5Gc due to the inactive CMAHP enzyme, Neu5Gc is present in food and must be degraded.
Gene Name:: RENBP
Uniprot ID:: P51606
Molecular weight:: 48830.6

Reactions

N-Acetyl-D-glucosamine → N-Acetylmannosamine	details

References

Lee YC, Wu HM, Chang YN, Wang WC, Hsu WH: The central cavity from the (alpha/alpha)6 barrel structure of Anabaena sp. CH1 N-acetyl-D-glucosamine 2-epimerase contains two key histidine residues for reversible conversion. J Mol Biol. 2007 Mar 30;367(3):895-908. Epub 2006 Nov 6. [PubMed:17292397 ]
Lee YC, Chien HC, Hsu WH: Production of N-acetyl-D-neuraminic acid by recombinant whole cells expressing Anabaena sp. CH1 N-acetyl-D-glucosamine 2-epimerase and Escherichia coli N-acetyl-D-neuraminic acid lyase. J Biotechnol. 2007 May 1;129(3):453-60. Epub 2007 Feb 9. [PubMed:17349707 ]
Takahashi S, Ogasawara H, Hiwatashi K, Hata K, Hori K, Koizumi Y, Sugiyama T: Amino acid residues conferring the nucleotide binding properties of N-acetyl-D-glucosamine 2-epimerase (renin binding protein). Biomed Res. 2005 Jun;26(3):117-21. [PubMed:16011304 ]
Ferrero MA, Martinez-Blanco H, Lopez-Velasco FF, Ezquerro-Saenz C, Navasa N, Lozano S, Rodriguez-Aparicio LB: Purification and characterization of GlcNAc-6-P 2-epimerase from Escherichia coli K92. Acta Biochim Pol. 2007;54(2):387-99. Epub 2007 Jun 14. [PubMed:17565386 ]

Enzyme Details

3. Beta-1,4-galactosyltransferase 2

General function:: Involved in transferase activity, transferring glycosyl groups
Specific function:: Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids. Can produce lactose.
Gene Name:: B4GALT2
Uniprot ID:: O60909
Molecular weight:: 41971.815

Reactions

Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosamine	details

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

4. Beta-1,4-galactosyltransferase 1

General function:: Involved in transferase activity, transferring glycosyl groups
Specific function:: The Golgi complex form catalyzes the production of lactose in the lactating mammary gland and could also be responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids. The cell surface form functions as a recognition molecule during a variety of cell to cell and cell to matrix interactions, as those occurring during development and egg fertilization, by binding to specific oligosaccharide ligands on opposing cells or in the extracellular matrix.
Gene Name:: B4GALT1
Uniprot ID:: P15291
Molecular weight:: 43919.895

Reactions

Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosamine	details

References

Ramakrishnan B, Boeggeman E, Qasba PK: Mutation of arginine 228 to lysine enhances the glucosyltransferase activity of bovine beta-1,4-galactosyltransferase I. Biochemistry. 2005 Mar 8;44(9):3202-10. [PubMed:15736931 ]
Ramasamy V, Ramakrishnan B, Boeggeman E, Ratner DM, Seeberger PH, Qasba PK: Oligosaccharide preferences of beta1,4-galactosyltransferase-I: crystal structures of Met340His mutant of human beta1,4-galactosyltransferase-I with a pentasaccharide and trisaccharides of the N-glycan moiety. J Mol Biol. 2005 Oct 14;353(1):53-67. [PubMed:16157350 ]
Boeggeman E, Ramakrishnan B, Kilgore C, Khidekel N, Hsieh-Wilson LC, Simpson JT, Qasba PK: Direct identification of nonreducing GlcNAc residues on N-glycans of glycoproteins using a novel chemoenzymatic method. Bioconjug Chem. 2007 May-Jun;18(3):806-14. Epub 2007 Mar 20. [PubMed:17370997 ]
Hidalgo A, Burgos V, Viola H, Medina J, Argibay P: Differential expression of glycans in the hippocampus of rats trained on an inhibitory learning paradigm. Neuropathology. 2006 Dec;26(6):501-7. [PubMed:17203585 ]
Ramakrishnan B, Boeggeman E, Qasba PK: Effect of the Met344His mutation on the conformational dynamics of bovine beta-1,4-galactosyltransferase: crystal structure of the Met344His mutant in complex with chitobiose. Biochemistry. 2004 Oct 5;43(39):12513-22. [PubMed:15449940 ]

Enzyme Details

5. Beta-hexosaminidase subunit beta

General function:: Involved in beta-N-acetylhexosaminidase activity
Specific function:: Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues.
Gene Name:: HEXB
Uniprot ID:: P07686
Molecular weight:: Not Available

Enzyme Details

6. Beta-hexosaminidase subunit alpha

General function:: Involved in beta-N-acetylhexosaminidase activity
Specific function:: Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues. The form B is active against certain oligosaccharides. The form S has no measurable activity.
Gene Name:: HEXA
Uniprot ID:: P06865
Molecular weight:: Not Available

Enzyme Details

7. N-acetyl-D-glucosamine kinase

General function:: Carbohydrate transport and metabolism
Specific function:: Converts endogenous N-acetylglucosamine (GlcNAc), a major component of complex carbohydrates, from lysosomal degradation or nutritional sources into GlcNAc 6-phosphate. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway: although human is not able to catalyze formation of Neu5Gc due to the inactive CMAHP enzyme, Neu5Gc is present in food and must be degraded. Also has ManNAc kinase activity.
Gene Name:: NAGK
Uniprot ID:: Q9UJ70
Molecular weight:: 42037.295

Reactions

Adenosine triphosphate + N-Acetyl-D-glucosamine → ADP + N-Acetyl-D-Glucosamine 6-Phosphate	details

References

Weihofen WA, Berger M, Chen H, Saenger W, Hinderlich S: Structures of human N-Acetylglucosamine kinase in two complexes with N-Acetylglucosamine and with ADP/glucose: insights into substrate specificity and regulation. J Mol Biol. 2006 Dec 1;364(3):388-99. Epub 2006 Sep 3. [PubMed:17010375 ]
Uehara T, Park JT: The N-acetyl-D-glucosamine kinase of Escherichia coli and its role in murein recycling. J Bacteriol. 2004 Nov;186(21):7273-9. [PubMed:15489439 ]
An HJ, Kim DS, Park YK, Kim SK, Choi YP, Kang S, Ding B, Cho NH: Comparative proteomics of ovarian epithelial tumors. J Proteome Res. 2006 May;5(5):1082-90. [PubMed:16674097 ]
Yang C, Rodionov DA, Li X, Laikova ON, Gelfand MS, Zagnitko OP, Romine MF, Obraztsova AY, Nealson KH, Osterman AL: Comparative genomics and experimental characterization of N-acetylglucosamine utilization pathway of Shewanella oneidensis. J Biol Chem. 2006 Oct 6;281(40):29872-85. Epub 2006 Jul 20. [PubMed:16857666 ]
Nishimasu H, Fushinobu S, Shoun H, Wakagi T: Crystal structures of an ATP-dependent hexokinase with broad substrate specificity from the hyperthermophilic archaeon Sulfolobus tokodaii. J Biol Chem. 2007 Mar 30;282(13):9923-31. Epub 2007 Jan 17. [PubMed:17229727 ]

Enzyme Details

8. Acidic mammalian chitinase

General function:: Involved in chitin binding
Specific function:: Degrades chitin and chitotriose. May participate in the defense against nematodes, fungi and other pathogens. Plays a role in T-helper cell type 2 (Th2) immune response. Contributes to the response to IL-13 and inflammation in response to IL-13. Stimulates chemokine production by pulmonary epithelial cells. Protects lung epithelial cells against apoptosis and promotes phosphorylation of AKT1. Its function in the inflammatory response and in protecting cells against apoptosis is inhibited by allosamidin, suggesting that the function of this protein depends on carbohydrate binding.
Gene Name:: CHIA
Uniprot ID:: Q9BZP6
Molecular weight:: Not Available

Reactions

Chitin + Water → N-Acetyl-D-glucosamine + Chitin	details

Enzyme Details

9. N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase

General function:: Involved in N-acetylglucosamine-1-phosphodiester alpha-
Specific function:: Catalyzes the second step in the formation of the mannose 6-phosphate targeting signal on lysosomal enzyme oligosaccharides by removing GlcNAc residues from GlcNAc-alpha-P-mannose moieties, which are formed in the first step.
Gene Name:: NAGPA
Uniprot ID:: Q9UK23
Molecular weight:: 56072.49

Reactions

Glycoprotein N-acetyl-D-glucosaminyl-phospho-D-mannose + Water → N-Acetyl-D-glucosamine + glycoprotein phospho-D-mannose	details

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Mullis KG, Huynh M, Kornfeld RH: Purification and kinetic parameters of bovine liver N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase. J Biol Chem. 1994 Jan 21;269(3):1718-26. [PubMed:8294420 ]
Chavez CA, Bohnsack RN, Kudo M, Gotschall RR, Canfield WM, Dahms NM: Domain 5 of the cation-independent mannose 6-phosphate receptor preferentially binds phosphodiesters (mannose 6-phosphate N-acetylglucosamine ester). Biochemistry. 2007 Nov 6;46(44):12604-17. Epub 2007 Oct 10. [PubMed:17927214 ]
Kornfeld R, Bao M, Brewer K, Noll C, Canfield WM: Purification and multimeric structure of bovine N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase. J Biol Chem. 1998 Sep 4;273(36):23203-10. [PubMed:9722550 ]

Enzyme Details

10. Chitotriosidase-1

General function:: Involved in chitin binding
Specific function:: Degrades chitin, chitotriose and chitobiose. May participate in the defense against nematodes and other pathogens. Isoform 3 has no enzymatic activity.
Gene Name:: CHIT1
Uniprot ID:: Q13231
Molecular weight:: Not Available

Reactions

Chitin + Water → N-Acetyl-D-glucosamine + Chitin	details

Only showing the first 10 proteins. There are 23 proteins in total.

Show all enzymes and transporters

Showing metabocard for N-Acetyl-D-glucosamine (HMDB0000215)

MOL for HMDB0000215 (N-Acetyl-D-glucosamine)

3D MOL for HMDB0000215 (N-Acetyl-D-glucosamine)

3D SDF for HMDB0000215 (N-Acetyl-D-glucosamine)

3D-SDF for HMDB0000215 (N-Acetyl-D-glucosamine)

PDB for HMDB0000215 (N-Acetyl-D-glucosamine)

3D PDB for HMDB0000215 (N-Acetyl-D-glucosamine)

SMILES for HMDB0000215 (N-Acetyl-D-glucosamine)

INCHI for HMDB0000215 (N-Acetyl-D-glucosamine)

Structure for HMDB0000215 (N-Acetyl-D-glucosamine)

3D Structure for HMDB0000215 (N-Acetyl-D-glucosamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

References

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