MiMeDB: Showing metabocard for N-Acetyl-D-glucosamine (MMDBc0000073)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:29:23 UTC

Update Date

2024-04-30 19:30:59 UTC

Metabolite ID

MMDBc0000073

Metabolite Identification

Common Name

N-Acetyl-D-glucosamine

Description

N-Acetyl-D-Glucosamine (N-acetlyglucosamine) is a monosaccharide derivative of glucose. Chemically it is an amide between glucosamine and acetic acid. A single N-acetlyglucosamine moiety linked to serine or threonine residues on nuclear and cytoplasmic proteins -O-GlcNAc, is an ubiquitous post-translational protein modification. O-GlcNAc modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly. O-GlcNAc regulates cellular responses to hormones such as insulin, initiates a protective response to stress, modulates a cell's capacity to grow and divide, and regulates gene transcription. In humans, it exists in skin, cartilage and blood vessel as a component of hyaluronic acid, and bone tissue, cornea and aorta as a component of keratan sulfate. (PMID 16237703 ).

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>
MMDBc0000073

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₈H₁₅NO₆

Average Mass

221.2078

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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)	-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

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Lysosome
Membrane

Biospecimen Locations

Blood
Breast Milk
Feces
Intestine
Neuron
Placenta
Platelet
Prostate
Saliva
Urine

Tissue Locations

Intestine
Neuron
Placenta
Platelet
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192001	Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase	Enzyme	Q9Y223	Homo sapiens
MMDBp0192003	N-acylglucosamine 2-epimerase	Enzyme	P51606	Homo sapiens
MMDBp0192038	Beta-1,4-galactosyltransferase 2	Unknown	O60909	Homo sapiens
MMDBp0192044	Beta-1,4-galactosyltransferase 1	Unknown	P15291	Homo sapiens
MMDBp0192489	Beta-hexosaminidase subunit beta	Enzyme	P07686	Homo sapiens
MMDBp0192490	Beta-hexosaminidase subunit alpha	Enzyme	P06865	Homo sapiens
MMDBp0192639	N-acetyl-D-glucosamine kinase	Enzyme	Q9UJ70	Homo sapiens
MMDBp0192640	Acidic mammalian chitinase	Enzyme	Q9BZP6	Homo sapiens
MMDBp0192641	N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase	Enzyme	Q9UK23	Homo sapiens
MMDBp0192642	Chitotriosidase-1	Enzyme	Q13231	Homo sapiens
MMDBp0192643	Beta-1,4-galactosyltransferase 3	Unknown	O60512	Homo sapiens
MMDBp0192644	Beta-1,4-galactosyltransferase 4	Unknown	O60513	Homo sapiens
MMDBp0193148	Alpha-N-acetylglucosaminidase	Enzyme	P54802	Homo sapiens
MMDBp0193151	Lysozyme C	Enzyme	P61626	Homo sapiens
MMDBp0195618	Protein O-linked-mannose beta-1,2-N-acetylglucosaminyltransferase 1	Unknown	Q8WZA1	Homo sapiens
MMDBp0196203	Lysozyme-like protein 1	Enzyme	Q6UWQ5	Homo sapiens
MMDBp0196223	Lysozyme-like protein 2	Enzyme	Q7Z4W2	Homo sapiens
MMDBp0196224	Sperm acrosome-associated protein 5	Enzyme	Q96QH8	Homo sapiens
MMDBp0196225	Lysozyme-like protein 6	Enzyme	O75951	Homo sapiens
MMDBp0196710	Chitinase-3-like protein 1	Unknown	P36222
MMDBp0196711	Chitinase-3-like protein 2	Unknown	Q15782
MMDBp0196839	Hexosaminidase D	Unknown	Q8WVB3
MMDBp0196905	Bifunctional protein NCOAT	Unknown	O60502

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018437	N-Acetyl-D-glucosamine	N-Acetyl-D-Glucosamine 6-Phosphate	N-acetyl-D-glucosamine kinase	Phosphorylation	PathBank	31602464
MMDBr0018438	Chitobiose	N-Acetyl-D-glucosamine	Beta-hexosaminidase	Cleavage of GlcNAc linked beta-1,4 to MurNAc tripeptides	PathBank	31602464
MMDBr0018440	Chitin	N-Acetyl-D-glucosamine	Probable bifunctional chitinase/lysozyme		PathBank	31602464
MMDBr0019280	N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid	N-Acetyl-D-glucosamine	Beta-hexosaminidase	Cleavage of GlcNAc linked beta-1,4 to MurNAc tripeptides	PathBank	31602464
MMDBr0025316	N-Acetyl-D-glucosamine	L-Histidine	PTS system N-acetylglucosamine-specific EIICBA component	Phosphorylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva; Human supragingival plaque	Microbial culture
Bacteria/Eubacteria	Bacteroidetes	196	Human feces; Human stool; Human urine; Human ; Human appendix biopsy; Human saliva; Human supragingival plaque; Human subgingival plaque; Human gastric fluid	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	588	Human feces; Human ; Human stool; Human pleural fluid plaque; Pig ; Human urine; Human mucosa; Human sputum; Human saliva; Human supragingival plaque; Cattle ; Human subgingival plaque	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	289	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Chicken ; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	3	Human feces; Human stool; Human ; Human urine	Microbial culture; Metabolic reconstruction
Eukaryota	Euglenozoa	1		Microbial culture
Bacteria/Eubacteria	Spirochaetes	4	Human feces	Microbial culture; Metabolic reconstruction
Bacteria	Actinobacteria	23	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human saliva; Human supragingival plaque; Human subgingival plaque; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	177	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human saliva; Human supragingival plaque; Human subgingival plaque; Human stool	Metabolic reconstruction
Bacteria	Firmicutes	45	Human feces; Human ; Human stool; Human pleural fluid plaque; Pig ; Human urine; Human mucosa; Human sputum; Human saliva; Human supragingival plaque; Cattle ; Human subgingival plaque	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	21	Human feces; Human	Metabolic reconstruction
Bacteria	Proteobacteria	17	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Chicken ; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Archaea	Euryarchaeota	3	Human feces	Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	3	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	3	Human feces	Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	2	Human feces	Metabolic reconstruction

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Breast milk	Detected and Quantified	204.3278984		uM	Adult (>18 years old)	Female	Normal	HMDB	11787731
Human Urine	Detected and Quantified	2.96	1.85	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	2026685
Human Saliva	Detected and Quantified	2.23	1.83	uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	2.40	2.35	uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	21.4	18.6	uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	3.14	2.38	uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	3.78	3.93	uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	4.41	5.98	uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Intestine	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Feces	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified				Infant (0-1 year old)	Both	Normal	HMDB	22411374
Human Feces	Detected but not Quantified				Adult (>18 years old)	Not Specified	Normal	HMDB	27622378
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified							HMDB

External Links

HMDB ID

HMDB0000215

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1007/BF00218559. [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. doi: 10.1016/s0015-0282(16)42624-5. [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. doi: 10.1016/S0002-9440(10)61779-8. [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. doi: 10.1016/s0008-6215(00)90564-0. [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. doi: 10.1515/bchm3.1989.370.2.1285. [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. doi: 10.1007/BF00269544. [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. doi: 10.1016/0008-6215(83)88020-3. [PubMed:6226355 ]
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 ]
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. doi: 10.1002/jcb.20676. [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 ]

Showing metabocard for N-Acetyl-D-glucosamine (MMDBc0000073)

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