NP-MRD: Showing NP-Card for N-Acetylgalactosamine (NP0000178)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-19 23:57:54 UTC

NP-MRD ID

NP0000178

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetylgalactosamine

Description

N-Acetylgalactosamine, also known as GalNAc, belongs to the class of organic compounds known as N-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an N-acyl group. N-Acetylgalactosamine is also classified as an amino sugar derivative of galactose. In humans GalNAc functions as the terminal carbohydrate forming the antigen of blood group A. GalNAc is typically the first monosaccharide that connects serine or threonine during protein O-glycosylation and the formation of glycoproteins. This is often referred to as mucin-type O-glycosylation, as the mucins (a class of a family of high molecular weight, heavily glycosylated proteins produced by epithelial tissues in most animals which have an ability to form gels) are heavily O-GalNAc modified. Interestingly, mammals have genes encoding for approximately 20 different polypeptide-N-acetylgalactosaminyltransferases (ppGalNAcTs), all of which transfer GalNAc from UDP-GalNAc to a hydroxyl-containing amino acids such as serine or threonine. N- O-GalNAc-containing glycoproteins appear to play a variety of essential roles. Among these is the ability of the mucins to hydrate and protect tissues by trapping bacteria. These O-glycans can also significantly alter the conformation of the protein and on the heavily modified proteins may protect the polypeptide from proteolytic digestion. O-GalNAc structures also appear to play an essential role in sperm–egg interactions. From a pathophysiological perspective, O-GalNAc modification appears to play a critical role in the immune system, cell–cell interactions, and cancer. N-Acetylgalactosamine is an important constituent of brain heteropolysaccharides (glycoproteins). The concentration of the N-acetylgalactosamine-containing glycoproteins in the 3-year-old cerebral gray matter from human brain is 7-15 times greater than in 8-year old tissue and 15-30 times greater than in 72-year-old tissue. Outside of the human body, N-Acetylgalactosamine has been detected, but not quantified in, several different foods, such as prickly pears, italian sweet red peppers, wheats, silver lindens, and sour cherries. This could make N-acetylgalactosamine a potential biomarker for the consumption of these foods.

Structure

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

HMDB0000212
     RDKit          3D
N-Acetylgalactosamine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.4214    0.7191    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9689    0.9921    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6037    2.2003    0.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0239   -0.0557   -0.0041 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6347    0.2374    0.0313 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0315   -0.2437   -1.2278 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5223   -1.4723   -1.5664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3915   -0.2186   -1.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9899   -0.7543   -0.1010 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4812   -0.5182   -0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7903    0.8380   -0.2058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -0.0162    1.1460 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4870    1.3620    0.8605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -0.4181    1.2502 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5569    0.0121    2.4163 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899    0.5040   -0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0248    1.5361    0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6346   -0.2034    0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3622   -1.0291   -0.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4521    1.3129    0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3011    0.4703   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -2.1509   -0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7924   -1.8191    0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9851   -1.0824   -0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017   -0.8914    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6783    1.0437    0.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0677   -0.2629    2.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5635    1.5405   -0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199   -1.5100    1.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0842   -0.1220    3.1596 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  6
  7 22  1  0
  9 23  1  1
 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

Untitled Document-1
  Mrv1652305271900222D          

 15 15  0  0  0  0            999 V2000
   -1.4289    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.6500    0.0000 O   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
  6  1  1  0  0  0  0
  1  7  1  1  0  0  0
  2  8  1  1  0  0  0
  3  9  1  1  0  0  0
  4 10  1  6  0  0  0
  5 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  7 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000178

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8+/m1/s1

> <INCHI_KEY>
OVRNDRQMDRJTHS-CBQIKETKSA-N

> <FORMULA>
C8H15NO6

> <MOLECULAR_WEIGHT>
221.2078

> <EXACT_MASS>
221.089937217

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
20.581216896348444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.60

> <JCHEM_LOGP>
-3.220574411666667

> <ALOGPS_LOGS>
0.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.811681816700894

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.604129514800414

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5720778168170417

> <JCHEM_POLAR_SURFACE_AREA>
119.25000000000001

> <JCHEM_REFRACTIVITY>
47.024699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-GalNAc

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000212
     RDKit          3D
N-Acetylgalactosamine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.4214    0.7191    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9689    0.9921    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6037    2.2003    0.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0239   -0.0557   -0.0041 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6347    0.2374    0.0313 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0315   -0.2437   -1.2278 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5223   -1.4723   -1.5664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3915   -0.2186   -1.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9899   -0.7543   -0.1010 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4812   -0.5182   -0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7903    0.8380   -0.2058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -0.0162    1.1460 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4870    1.3620    0.8605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -0.4181    1.2502 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5569    0.0121    2.4163 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899    0.5040   -0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0248    1.5361    0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6346   -0.2034    0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3622   -1.0291   -0.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4521    1.3129    0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3011    0.4703   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -2.1509   -0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7924   -1.8191    0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9851   -1.0824   -0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017   -0.8914    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6783    1.0437    0.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0677   -0.2629    2.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5635    1.5405   -0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199   -1.5100    1.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0842   -0.1220    3.1596 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  6
  7 22  1  0
  9 23  1  1
 10 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  1
 13 28  1  0
 14 29  1  6
 15 30  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-1                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.667   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.001   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.001  -1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334  -3.080   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       1.334  -1.540   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       1.334   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   0.770   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.001   3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    1                                                       
CONECT    7    1   15                                                       
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4   12                                                       
CONECT   11    5                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    7                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0000212
HETATM    1  C1  UNL     1       4.421   0.719   0.037  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.969   0.992   0.072  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.604   2.200   0.172  1.00  0.00           O  
HETATM    4  N1  UNL     1       2.024  -0.056  -0.004  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.635   0.237   0.031  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.031  -0.244  -1.228  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.522  -1.472  -1.566  1.00  0.00           O  
HETATM    8  O3  UNL     1      -1.391  -0.219  -1.203  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.990  -0.754  -0.101  1.00  0.00           C  
HETATM   10  C6  UNL     1      -3.481  -0.518  -0.163  1.00  0.00           C  
HETATM   11  O4  UNL     1      -3.790   0.838  -0.206  1.00  0.00           O  
HETATM   12  C7  UNL     1      -1.491  -0.016   1.146  1.00  0.00           C  
HETATM   13  O5  UNL     1      -1.487   1.362   0.861  1.00  0.00           O  
HETATM   14  C8  UNL     1      -0.023  -0.418   1.250  1.00  0.00           C  
HETATM   15  O6  UNL     1       0.557   0.012   2.416  1.00  0.00           O  
HETATM   16  H1  UNL     1       4.790   0.504  -0.986  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.025   1.536   0.450  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.635  -0.203   0.650  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.362  -1.029  -0.085  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.452   1.313   0.119  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.301   0.470  -2.040  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.442  -2.151  -0.867  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.792  -1.819   0.082  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.985  -1.082  -0.956  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.902  -0.891   0.816  1.00  0.00           H  
HETATM   26  H11 UNL     1      -4.678   1.044   0.149  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.068  -0.263   2.034  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.563   1.541  -0.098  1.00  0.00           H  
HETATM   29  H14 UNL     1       0.020  -1.510   1.088  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.084  -0.122   3.160  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

HMDB0000212
     RDKit          3D
N-Acetylgalactosamine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.4214    0.7191    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9689    0.9921    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6037    2.2003    0.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0239   -0.0557   -0.0041 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6347    0.2374    0.0313 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0315   -0.2437   -1.2278 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5223   -1.4723   -1.5664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3915   -0.2186   -1.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9899   -0.7543   -0.1010 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4812   -0.5182   -0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7903    0.8380   -0.2058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -0.0162    1.1460 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4870    1.3620    0.8605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -0.4181    1.2502 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5569    0.0121    2.4163 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899    0.5040   -0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0248    1.5361    0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6346   -0.2034    0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3622   -1.0291   -0.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4521    1.3129    0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3011    0.4703   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -2.1509   -0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7924   -1.8191    0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9851   -1.0824   -0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017   -0.8914    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6783    1.0437    0.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0677   -0.2629    2.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5635    1.5405   -0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199   -1.5100    1.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0842   -0.1220    3.1596 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  6
  7 22  1  0
  9 23  1  1
 10 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  1
 13 28  1  0
 14 29  1  6
 15 30  1  0
M  END

View in JSmol

Synonyms

Value	Source
2-(Acetylamino)-2-deoxy-alpha-D-galactopyranose	ChEBI
alpha-GalNAc	ChEBI
alpha-GalpNAc	ChEBI
GalNAc-alpha	ChEBI
Tn	ChEBI
TN Antigen saccharide	ChEBI
TN Antigen saccharide component	ChEBI
TN Saccharide	ChEBI
TN Saccharide component	ChEBI
WURCS=2.0/1,1,0/[a2112h-1a_1-5_2*ncc/3=o]/1/	ChEBI
2-(Acetylamino)-2-deoxy-a-D-galactopyranose	Generator
2-(Acetylamino)-2-deoxy-α-D-galactopyranose	Generator
a-GalNAc	Generator
Α-galnac	Generator
a-GalpNAc	Generator
Α-galpnac	Generator
GalNAc-a	Generator
GalNAc-α	Generator
2-Acetamido-2-deoxy-a-D-allopyranose	HMDB
2-Acetamido-2-deoxy-a-D-glucopyranose	HMDB
2-Acetamido-2-deoxy-alpha-D-allopyranose	HMDB
2-Acetamido-2-deoxy-alpha-D-glucopyranose	HMDB
2-Acetamido-2-deoxy-alpha-delta-allopyranose	HMDB
2-Acetamido-2-deoxy-alpha-delta-glucopyranose	HMDB
2-Acetamido-2-deoxy-b-D-glucopyranose	HMDB
2-Acetamido-2-deoxy-beta-D-glucopyranose	HMDB
2-Acetamido-2-deoxy-beta-delta-glucopyranose	HMDB
2-Acetamido-2-desoxy-b-D-talofuranose	HMDB
2-Acetamido-2-desoxy-beta-D-talofuranose	HMDB
2-Acetamido-2-desoxy-beta-delta-talofuranose	HMDB
2-Acetamino-2-deoxy-a-D-glucose	HMDB
2-Acetamino-2-deoxy-alpha-D-glucose	HMDB
2-Acetamino-2-deoxy-alpha-delta-glucose	HMDB
2-Acetamino-2-desoxy-a-D-glucopyranose	HMDB
2-Acetamino-2-desoxy-alpha-D-glucopyranose	HMDB
2-Acetamino-2-desoxy-alpha-delta-glucopyranose	HMDB
2-Acetamino-2-desoxy-D-galaktose	HMDB
2-Acetamino-2-desoxy-D-glucose	HMDB
2-Acetamino-2-desoxy-delta-galaktose	HMDB
2-Acetamino-2-desoxy-delta-glucose	HMDB
2-Acetylamino-2-deoxy-a-D-galactopyranose	HMDB
2-Acetylamino-2-deoxy-a-D-glucopyranose	HMDB
2-Acetylamino-2-deoxy-a-D-mannopyranose	HMDB
2-Acetylamino-2-deoxy-alpha-D-galactopyranose	HMDB
2-Acetylamino-2-deoxy-alpha-D-glucopyranose	HMDB
2-Acetylamino-2-deoxy-alpha-D-mannopyranose	HMDB
2-Acetylamino-2-deoxy-alpha-delta-galactopyranose	HMDB
2-Acetylamino-2-deoxy-alpha-delta-glucopyranose	HMDB
2-Acetylamino-2-deoxy-alpha-delta-mannopyranose	HMDB
2-Acetylamino-2-deoxy-b-D-allopyranose	HMDB
2-Acetylamino-2-deoxy-b-D-altropyranose	HMDB
2-Acetylamino-2-deoxy-b-D-galactopyranose	HMDB
2-Acetylamino-2-deoxy-b-D-glucopyranose	HMDB
2-Acetylamino-2-deoxy-b-D-mannopyranose	HMDB
2-Acetylamino-2-deoxy-beta-D-allopyranose	HMDB
2-Acetylamino-2-deoxy-beta-D-altropyranose	HMDB
2-Acetylamino-2-deoxy-beta-D-galactopyranose	HMDB
2-Acetylamino-2-deoxy-beta-D-glucopyranose	HMDB
2-Acetylamino-2-deoxy-beta-D-mannopyranose	HMDB
2-Acetylamino-2-deoxy-beta-delta-allopyranose	HMDB
2-Acetylamino-2-deoxy-beta-delta-altropyranose	HMDB
2-Acetylamino-2-deoxy-beta-delta-galactopyranose	HMDB
2-Acetylamino-2-deoxy-beta-delta-glucopyranose	HMDB
2-Acetylamino-2-deoxy-beta-delta-mannopyranose	HMDB
2-Acetylamino-2-desoxy-a-D-galaktose	HMDB
2-Acetylamino-2-desoxy-a-D-mannose	HMDB
2-Acetylamino-2-desoxy-alpha-D-galaktose	HMDB
2-Acetylamino-2-desoxy-alpha-D-mannose	HMDB
2-Acetylamino-2-desoxy-alpha-delta-galaktose	HMDB
2-Acetylamino-2-desoxy-alpha-delta-mannose	HMDB
2-Acetylamino-2-desoxy-b-D-galaktose	HMDB
2-Acetylamino-2-desoxy-b-D-mannose	HMDB
2-Acetylamino-2-desoxy-beta-D-galaktose	HMDB
2-Acetylamino-2-desoxy-beta-D-mannose	HMDB
2-Acetylamino-2-desoxy-beta-delta-galaktose	HMDB
2-Acetylamino-2-desoxy-beta-delta-mannose	HMDB
2-Acetylamino-2-desoxy-D-mannose	HMDB
2-Acetylamino-2-desoxy-delta-mannose	HMDB
2-Acetylamino-2-desoxy-DL-glucopyranose	HMDB
2-Acetylamino-a-D-2-deoxy-galactopyranose	HMDB
2-Acetylamino-a-D-2-deoxy-glucopyranose	HMDB
2-Acetylamino-a-D-2-deoxy-glucose	HMDB
2-Acetylamino-a-D-2-deoxy-mannopyranose	HMDB
2-Acetylamino-alpha-D-2-deoxy-galactopyranose	HMDB
2-Acetylamino-alpha-D-2-deoxy-glucopyranose	HMDB
2-Acetylamino-alpha-D-2-deoxy-glucose	HMDB
2-Acetylamino-alpha-D-2-deoxy-mannopyranose	HMDB
2-Acetylamino-alpha-delta-2-deoxy-galactopyranose	HMDB
2-Acetylamino-alpha-delta-2-deoxy-glucopyranose	HMDB
2-Acetylamino-alpha-delta-2-deoxy-glucose	HMDB
2-Acetylamino-alpha-delta-2-deoxy-mannopyranose	HMDB
2-Acetylamino-b-D-2-deoxy-galactopyranose	HMDB
2-Acetylamino-b-D-2-deoxy-glucopyranose	HMDB
2-Acetylamino-b-D-2-deoxy-mannopyranose	HMDB
2-Acetylamino-beta-D-2-deoxy-galactopyranose	HMDB
2-Acetylamino-beta-D-2-deoxy-glucopyranose	HMDB
2-Acetylamino-beta-D-2-deoxy-mannopyranose	HMDB
2-Acetylamino-beta-delta-2-deoxy-galactopyranose	HMDB
2-Acetylamino-beta-delta-2-deoxy-glucopyranose	HMDB
2-Acetylamino-beta-delta-2-deoxy-mannopyranose	HMDB
2-Acetylamino-D-2-deoxy-galactose	HMDB
2-Acetylamino-D-2-deoxy-glucose	HMDB
2-Acetylamino-D-2-deoxy-gulose	HMDB
2-Acetylamino-D-2-deoxy-idose	HMDB
2-Acetylamino-D-2-deoxy-mannose	HMDB
2-Acetylamino-D-2-deoxy-talose	HMDB
2-Acetylamino-delta-2-deoxy-galactose	HMDB
2-Acetylamino-delta-2-deoxy-glucose	HMDB
2-Acetylamino-delta-2-deoxy-gulose	HMDB
2-Acetylamino-delta-2-deoxy-idose	HMDB
2-Acetylamino-delta-2-deoxy-mannose	HMDB
2-Acetylamino-delta-2-deoxy-talose	HMDB
2-Acetylamino-L-2-deoxy-galactose	HMDB
2-Acetylamino-L-2-deoxy-mannose	HMDB
a-2-Acetamido-2-deoxy-D-galactose	HMDB
alpha-2-Acetamido-2-deoxy-D-galactose	HMDB
alpha-2-Acetamido-2-deoxy-delta-galactose	HMDB
GalNAc	HMDB
N-(2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide	HMDB
N-Acetyl-a-D-glucosamine	HMDB
N-Acetyl-alpha-D-glucosamine	HMDB
N-Acetyl-alpha-delta-glucosamine	HMDB
N-Acetyl-D-allosamine	HMDB
N-Acetyl-D-galactosamine	HMDB
N-Acetyl-delta-allosamine	HMDB
N-Acetyl-delta-galactosamine	HMDB
N-Acetylgalactosamin	HMDB
N-Acetylglucosamin	HMDB
N-Acetylgluosamin	HMDB
N-Acetylmannosamin	HMDB
2 Acetamido 2 deoxy D galactose	HMDB
2-Acetamido-2-D-galactopyranose	HMDB
Acetylgalactosamine	HMDB
2-Acetamido-2-deoxygalactose	HMDB
N Acetyl D galactosamine	HMDB
2 Acetamido 2 D galactopyranose	HMDB
2 Acetamido 2 deoxygalactose	HMDB
2-Acetamido-2-deoxy-D-galactose	HMDB
N-Acetyl-a-D-galactosamine	HMDB
N-Acetyl-α-D-galactosamine	HMDB
a-N-Acetyl-D-galactosamine	HMDB
Α-N-acetyl-D-galactosamine	HMDB

Chemical Formula

C₈H₁₅NO₆

Average Mass

221.2078 Da

Monoisotopic Mass

221.08994 Da

IUPAC Name

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

Traditional Name

α-GalNAc

CAS Registry Number

1811-31-0

SMILES

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

InChI Identifier

InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8+/m1/s1

InChI Key

OVRNDRQMDRJTHS-CBQIKETKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acyl-alpha-hexosamines

Alternative Parents

Substituents

N-acyl-alpha-hexosamine
Hexose monosaccharide
Monosaccharide
Oxane
Hemiacetal
Secondary alcohol
Carboximidic acid
Carboximidic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Alcohol
Organonitrogen compound
Organic nitrogen compound
Primary alcohol
Organopnictogen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acetyl-D-galactosamine (CHEBI:40356 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	172 - 173 °C	Not Available
Boiling Point	636.40 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-2.815 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
Water Solubility	254 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.2	ChemAxon
logS	0.06	ALOGPS
pKa (Strongest Acidic)	11.6	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	20.58 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000212

DrugBank ID

DB03567

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB031022

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

N-Acetylgalactosamine

METLIN ID

5222

PubChem Compound

84265

PDB ID

Not Available

ChEBI ID

40356

Good Scents ID

Not Available

References

General References

Mazany KD, Peng T, Watson CE, Tabas I, Williams KJ: Human chondroitin 6-sulfotransferase: cloning, gene structure, and chromosomal localization. Biochim Biophys Acta. 1998 Jul 1;1407(1):92-7. [PubMed:9639683 ]
Zhang Y, Iwasaki H, Wang H, Kudo T, Kalka TB, Hennet T, Kubota T, Cheng L, Inaba N, Gotoh M, Togayachi A, Guo J, Hisatomi H, Nakajima K, Nishihara S, Nakamura M, Marth JD, Narimatsu H: Cloning and characterization of a new human UDP-N-acetyl-alpha-D-galactosamine:polypeptide N-acetylgalactosaminyltransferase, designated pp-GalNAc-T13, that is specifically expressed in neurons and synthesizes GalNAc alpha-serine/threonine antigen. J Biol Chem. 2003 Jan 3;278(1):573-84. Epub 2002 Oct 28. [PubMed:12407114 ]
White T, Bennett EP, Takio K, Sorensen T, Bonding N, Clausen H: Purification and cDNA cloning of a human UDP-N-acetyl-alpha-D-galactosamine:polypeptide N-acetylgalactosaminyltransferase. J Biol Chem. 1995 Oct 13;270(41):24156-65. [PubMed:7592619 ]
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 ]
Kamakura K, Kaida K, Kusunoki S, Miyamoto N, Masaki T, Nakamura R, Motoyoshi K, Fukuda J: Harmful effects of anti-GalNAc-GD1a antibodies and TNF-alpha on rat dorsal root ganglia. J Peripher Nerv Syst. 2005 Jun;10(2):190-201. [PubMed:15958130 ]
Petri WA Jr, Chaudhry O, Haque R, Houpt E: Adherence-blocking vaccine for amebiasis. Arch Med Res. 2006 Feb;37(2):288-91. [PubMed:16380334 ]
Petry K, Greinix HT, Nudelman E, Eisen H, Hakomori S, Levy HL, Reichardt JK: Characterization of a novel biochemical abnormality in galactosemia: deficiency of glycolipids containing galactose or N-acetylgalactosamine and accumulation of precursors in brain and lymphocytes. Biochem Med Metab Biol. 1991 Aug;46(1):93-104. [PubMed:1931160 ]
Kaida K, Kusunoki S, Kamakura K, Motoyoshi K, Kanazawa I: GalNAc-GD1a in human peripheral nerve: target sites of anti-ganglioside antibody. Neurology. 2003 Aug 26;61(4):465-70. [PubMed:12939418 ]
Gupta D, Sabesan S, Brewer CF: Selective inhibition of N-acetylglucosamine and galactose-specific lectins including the 14-kDa vertebrate lectin by novel synthetic biantennary oligosaccharides. Eur J Biochem. 1993 Sep 15;216(3):789-97. [PubMed:8404897 ]
Sutherlin ME, Nishimori I, Caffrey T, Bennett EP, Hassan H, Mandel U, Mack D, Iwamura T, Clausen H, Hollingsworth MA: Expression of three UDP-N-acetyl-alpha-D-galactosamine:polypeptide GalNAc N-acetylgalactosaminyltransferases in adenocarcinoma cell lines. Cancer Res. 1997 Nov 1;57(21):4744-8. [PubMed:9354435 ]
Kariniemi AL, Virtanen I: Dolichos biflorus agglutinin (DBA) reveals a similar basal cell differentiation in normal and psoriatic epidermis. Histochemistry. 1989;93(2):129-32. [PubMed:2482277 ]
Yuki N: Infectious origins of, and molecular mimicry in, Guillain-Barre and Fisher syndromes. Lancet Infect Dis. 2001 Aug;1(1):29-37. [PubMed:11871407 ]
Tao X, Gao G, Zhang HZ, Zhu DX, Boersma A, Lamblin G, Han KK: Isolation and characterization of human urinary colony-stimulating factor. Biol Chem Hoppe Seyler. 1987 Mar;368(3):187-94. [PubMed:3496105 ]
Hiruma T, Togayachi A, Okamura K, Sato T, Kikuchi N, Kwon YD, Nakamura A, Fujimura K, Gotoh M, Tachibana K, Ishizuka Y, Noce T, Nakanishi H, Narimatsu H: A novel human beta1,3-N-acetylgalactosaminyltransferase that synthesizes a unique carbohydrate structure, GalNAcbeta1-3GlcNAc. J Biol Chem. 2004 Apr 2;279(14):14087-95. Epub 2004 Jan 14. [PubMed:14724282 ]
Chikakiyo H, Kunishige M, Yoshino H, Asano A, Sumitomo Y, Endo I, Matsumoto T, Mitsui T: Delayed motor and sensory neuropathy in a patient with brainstem encephalitis. J Neurol Sci. 2005 Jul 15;234(1-2):105-8. [PubMed:15936038 ]
Roelen HC, Bijsterbosch MK, Bakkeren HF, van Berkel TJ, Kempen HJ, Buytenhek M, van der Marel GA, van Boom JH: Water-soluble cholesteryl-containing phosphorothioate monogalactosides: synthesis, properties, and use in lowering blood cholesterol by directing plasma lipoproteins to the liver. J Med Chem. 1991 Mar;34(3):1036-42. [PubMed:2002447 ]
Smith PL, Bousfield GR, Kumar S, Fiete D, Baenziger JU: Equine lutropin and chorionic gonadotropin bear oligosaccharides terminating with SO4-4-GalNAc and Sia alpha 2,3Gal, respectively. J Biol Chem. 1993 Jan 15;268(2):795-802. [PubMed:8419356 ]
Szkudlinski MW, Thotakura NR, Tropea JE, Grossmann M, Weintraub BD: Asparagine-linked oligosaccharide structures determine clearance and organ distribution of pituitary and recombinant thyrotropin. Endocrinology. 1995 Aug;136(8):3325-30. [PubMed:7628367 ]
Taguchi K, Ren J, Utsunomiya I, Aoyagi H, Fujita N, Ariga T, Miyatake T, Yoshino H: Neurophysiological and immunohistochemical studies on Guillain-Barre syndrome with IgG anti-GalNAc-GD1a antibodies-effects on neuromuscular transmission. J Neurol Sci. 2004 Oct 15;225(1-2):91-8. [PubMed:15465091 ]
Hoyte K, Kang C, Martin PT: Definition of pre- and postsynaptic forms of the CT carbohydrate antigen at the neuromuscular junction: ubiquitous expression of the CT antigens and the CT GalNAc transferase in mouse tissues. Brain Res Mol Brain Res. 2002 Dec 30;109(1-2):146-60. [PubMed:12531524 ]
Brunngraber EG, Brown BD, Aro A: Distribution and age-dependent concentration in brain tissue of glycoproteins containing N-acetylgalactosamine. Neurobiology. 1975 Dec;5(6):339-46. [PubMed:1207868 ]
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Showing NP-Card for N-Acetylgalactosamine (NP0000178)

MOL for NP0000178 (N-Acetylgalactosamine)

3D MOL for NP0000178 (N-Acetylgalactosamine)

3D SDF for NP0000178 (N-Acetylgalactosamine)

3D-SDF for NP0000178 (N-Acetylgalactosamine)

PDB for NP0000178 (N-Acetylgalactosamine)

3D PDB for NP0000178 (N-Acetylgalactosamine)

SMILES for NP0000178 (N-Acetylgalactosamine)

INCHI for NP0000178 (N-Acetylgalactosamine)

Structure for NP0000178 (N-Acetylgalactosamine)

3D Structure for NP0000178 (N-Acetylgalactosamine)