NP-MRD: Showing NP-Card for N-Acetylgalactosamine 4-sulphate (NP0001155)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:44:13 UTC

NP-MRD ID

NP0001155

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetylgalactosamine 4-sulphate

Description

Also known as GalNAc4S, this molecule is a key component of dermatan, keratan and chondroitin sulfate. It is also a substrate for the enzyme N-acteylgalactosamine-4-sulphate transferase. This molecule is found in elevated concentrations in the urine of patients suffering from muchopolysaccharidosis type III, IV and VI. Levels are typically 300-400 times normal values. GalNAc4S is thought to be derived from the action of beta-N-acetylhexosaminidase on sulphated GlcNAc or GalNAc residues at the non-reducing end of keratan sulphate, dermatan sulphate or chondroitin sulphate.

Structure

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

HMDB0000781
     RDKit          3D
N-Acetylgalactosamine 4-sulphate
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.5667   -0.7997    0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1941   -0.2578    0.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7913    0.5133    1.4953 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3073   -0.5733   -0.4607 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -0.0868   -0.5963 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7025    0.6301   -1.8662 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3740    1.8599   -1.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5938    0.8306   -2.1653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5499    0.6721   -1.2163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8042    1.9465   -0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2241    2.9873   -1.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3876   -0.5202   -0.3281 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4652   -0.1044    1.0149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6604   -0.9083    1.8441 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.1236   -2.0644    2.6521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6123   -1.4862    0.8290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5149    0.0938    2.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0592   -1.2109   -0.5001 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2420   -2.0757    0.5187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6563   -1.8005    0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3442   -0.0988    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7605   -0.9857    1.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665   -1.2297   -1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7669    0.5778    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560    0.0090   -2.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817    2.1264   -2.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5262    0.5053   -1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6326    1.7640    0.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905    2.3007    0.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573    3.6039   -0.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1741   -1.2938   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4232   -0.2931    2.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0704   -1.6972   -1.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2214   -2.9341    0.3385 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
 13 14  1  0
 14 15  2  0
 14 16  2  0
 14 17  1  0
 12 18  1  0
 18 19  1  0
 18  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  1
  6 25  1  6
  7 26  1  0
  9 27  1  6
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  6
 17 32  1  0
 18 33  1  6
 19 34  1  0
M  END


  Mrv1652305271900222D          

 19 19  0  0  1  0            999 V2000
    6.3523   -7.4984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6707   -6.2609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9562   -6.6734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6707   -5.4359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2417   -6.2609    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9562   -5.0234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2417   -5.4359    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9562   -7.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6707   -7.9109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3852   -5.0234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273   -5.0234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273   -6.6734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273   -7.4984    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7022   -7.4984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273   -8.3234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9562   -4.1984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -3.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -2.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273   -4.1984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
  3  8  1  6  0  0  0
  9  8  1  0  0  0  0
  4 10  1  6  0  0  0
  7 11  1  6  0  0  0
  5 12  1  6  0  0  0
 13 12  1  0  0  0  0
  1 13  2  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
  6 16  1  1  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001155

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO9S/c1-3(11)9-5-6(12)7(18-19(14,15)16)4(2-10)17-8(5)13/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H,14,15,16)/t4-,5-,6-,7+,8-/m1/s1

> <INCHI_KEY>
WHCJUIFHMJFEFZ-UIAUGNHASA-N

> <FORMULA>
C8H15NO9S

> <MOLECULAR_WEIGHT>
301.271

> <EXACT_MASS>
301.046751773

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.949935776389268

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
-2.04

> <JCHEM_LOGP>
-4.920668676521459

> <ALOGPS_LOGS>
-0.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.463895971777568

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.0335881928679234

> <JCHEM_PKA_STRONGEST_BASIC>
-1.388425744710882

> <JCHEM_POLAR_SURFACE_AREA>
162.62

> <JCHEM_REFRACTIVITY>
57.0165

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.29e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000781
     RDKit          3D
N-Acetylgalactosamine 4-sulphate
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.5667   -0.7997    0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1941   -0.2578    0.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7913    0.5133    1.4953 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3073   -0.5733   -0.4607 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -0.0868   -0.5963 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7025    0.6301   -1.8662 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3740    1.8599   -1.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5938    0.8306   -2.1653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5499    0.6721   -1.2163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8042    1.9465   -0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2241    2.9873   -1.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3876   -0.5202   -0.3281 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4652   -0.1044    1.0149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6604   -0.9083    1.8441 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.1236   -2.0644    2.6521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6123   -1.4862    0.8290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5149    0.0938    2.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0592   -1.2109   -0.5001 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2420   -2.0757    0.5187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6563   -1.8005    0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3442   -0.0988    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7605   -0.9857    1.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665   -1.2297   -1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7669    0.5778    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560    0.0090   -2.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817    2.1264   -2.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5262    0.5053   -1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6326    1.7640    0.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905    2.3007    0.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573    3.6039   -0.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1741   -1.2938   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4232   -0.2931    2.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0704   -1.6972   -1.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2214   -2.9341    0.3385 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
 13 14  1  0
 14 15  2  0
 14 16  2  0
 14 17  1  0
 12 18  1  0
 18 19  1  0
 18  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  1
  6 25  1  6
  7 26  1  0
  9 27  1  6
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  6
 17 32  1  0
 18 33  1  6
 19 34  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      11.858 -13.997   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      14.319 -11.687   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.985 -12.457   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.319 -10.147   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.651 -11.687   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.985  -9.377   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.651 -10.147   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.985 -13.997   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.319 -14.767   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      15.652  -9.377   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      10.318  -9.377   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      10.318 -12.457   0.000  0.00  0.00           O+0
HETATM   13  S   UNK     0      10.318 -13.997   0.000  0.00  0.00           S+0
HETATM   14  O   UNK     0       8.777 -13.997   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.318 -15.537   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      12.985  -7.837   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      11.651  -7.067   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.651  -5.527   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.318  -7.837   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5    8                                                  
CONECT    4    2    6   10                                                  
CONECT    5    3    7   12                                                  
CONECT    6    4    7   16                                                  
CONECT    7    5    6   11                                                  
CONECT    8    3    9                                                       
CONECT    9    8                                                            
CONECT   10    4                                                            
CONECT   11    7                                                            
CONECT   12    5   13                                                       
CONECT   13   12    1   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    6   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0000781
HETATM    1  C1  UNL     1       4.567  -0.800   0.679  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.194  -0.258   0.596  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.791   0.513   1.495  1.00  0.00           O  
HETATM    4  N1  UNL     1       2.307  -0.573  -0.461  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.981  -0.087  -0.596  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.703   0.630  -1.866  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.374   1.860  -1.955  1.00  0.00           O  
HETATM    8  O3  UNL     1      -0.594   0.831  -2.165  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.550   0.672  -1.216  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.804   1.946  -0.406  1.00  0.00           C  
HETATM   11  O4  UNL     1      -2.224   2.987  -1.231  1.00  0.00           O  
HETATM   12  C7  UNL     1      -1.388  -0.520  -0.328  1.00  0.00           C  
HETATM   13  O5  UNL     1      -1.465  -0.104   1.015  1.00  0.00           O  
HETATM   14  S1  UNL     1      -2.660  -0.908   1.844  1.00  0.00           S  
HETATM   15  O6  UNL     1      -2.124  -2.064   2.652  1.00  0.00           O  
HETATM   16  O7  UNL     1      -3.612  -1.486   0.829  1.00  0.00           O  
HETATM   17  O8  UNL     1      -3.515   0.094   2.882  1.00  0.00           O  
HETATM   18  C8  UNL     1      -0.059  -1.211  -0.500  1.00  0.00           C  
HETATM   19  O9  UNL     1       0.242  -2.076   0.519  1.00  0.00           O  
HETATM   20  H1  UNL     1       4.656  -1.801   0.203  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.344  -0.099   0.344  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.761  -0.986   1.775  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.666  -1.230  -1.215  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.767   0.578   0.264  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.156   0.009  -2.696  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.282   2.126  -2.923  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.526   0.505  -1.767  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.633   1.764   0.310  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.890   2.301   0.103  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.857   3.604  -0.795  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.174  -1.294  -0.459  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.423  -0.293   2.979  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.070  -1.697  -1.498  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.221  -2.934   0.339  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3    4
CONECT    4    5   23
CONECT    5    6   18   24
CONECT    6    7    8   25
CONECT    7   26
CONECT    8    9
CONECT    9   10   12   27
CONECT   10   11   28   29
CONECT   11   30
CONECT   12   13   18   31
CONECT   13   14
CONECT   14   15   15   16   16
CONECT   14   17
CONECT   17   32
CONECT   18   19   33
CONECT   19   34
END

HMDB0000781
     RDKit          3D
N-Acetylgalactosamine 4-sulphate
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.5667   -0.7997    0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1941   -0.2578    0.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7913    0.5133    1.4953 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3073   -0.5733   -0.4607 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -0.0868   -0.5963 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7025    0.6301   -1.8662 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3740    1.8599   -1.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5938    0.8306   -2.1653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5499    0.6721   -1.2163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8042    1.9465   -0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2241    2.9873   -1.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3876   -0.5202   -0.3281 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4652   -0.1044    1.0149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6604   -0.9083    1.8441 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.1236   -2.0644    2.6521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6123   -1.4862    0.8290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5149    0.0938    2.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0592   -1.2109   -0.5001 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2420   -2.0757    0.5187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6563   -1.8005    0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3442   -0.0988    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7605   -0.9857    1.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665   -1.2297   -1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7669    0.5778    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560    0.0090   -2.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817    2.1264   -2.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5262    0.5053   -1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6326    1.7640    0.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905    2.3007    0.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573    3.6039   -0.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1741   -1.2938   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4232   -0.2931    2.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0704   -1.6972   -1.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2214   -2.9341    0.3385 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
 13 14  1  0
 14 15  2  0
 14 16  2  0
 14 17  1  0
 12 18  1  0
 18 19  1  0
 18  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  1
  6 25  1  6
  7 26  1  0
  9 27  1  6
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  6
 17 32  1  0
 18 33  1  6
 19 34  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
N-Acetyl-beta-D-galactosamine 4-sulphate	ChEBI
2-(Acetylamino)-2-deoxy-4-O-sulfO-beta-D-galactopyranose	ChEBI
2-Deoxy-2-acetamido-beta-D-galactose-4-sulfate	ChEBI
beta-D-GalpNAc4S	ChEBI
N-Acetyl-beta-D-galactosamine 4-sulfuric acid	ChEBI
N-Acetyl-b-D-galactosamine 4-sulfate	Generator
N-Acetyl-b-D-galactosamine 4-sulfuric acid	Generator
N-Acetyl-b-D-galactosamine 4-sulphate	Generator
N-Acetyl-b-D-galactosamine 4-sulphuric acid	Generator
N-Acetyl-beta-D-galactosamine 4-sulfate	Generator
N-Acetyl-beta-D-galactosamine 4-sulphuric acid	Generator
N-Acetyl-β-D-galactosamine 4-sulfate	Generator
N-Acetyl-β-D-galactosamine 4-sulfuric acid	Generator
N-Acetyl-β-D-galactosamine 4-sulphate	Generator
N-Acetyl-β-D-galactosamine 4-sulphuric acid	Generator
2-(Acetylamino)-2-deoxy-4-O-sulfO-b-D-galactopyranose	Generator
2-(Acetylamino)-2-deoxy-4-O-sulfO-β-D-galactopyranose	Generator
2-(Acetylamino)-2-deoxy-4-O-sulphO-b-D-galactopyranose	Generator
2-(Acetylamino)-2-deoxy-4-O-sulphO-beta-D-galactopyranose	Generator
2-(Acetylamino)-2-deoxy-4-O-sulphO-β-D-galactopyranose	Generator
2-Deoxy-2-acetamido-b-D-galactose-4-sulfate	Generator
2-Deoxy-2-acetamido-b-D-galactose-4-sulfuric acid	Generator
2-Deoxy-2-acetamido-b-D-galactose-4-sulphate	Generator
2-Deoxy-2-acetamido-b-D-galactose-4-sulphuric acid	Generator
2-Deoxy-2-acetamido-beta-D-galactose-4-sulfuric acid	Generator
2-Deoxy-2-acetamido-beta-D-galactose-4-sulphate	Generator
2-Deoxy-2-acetamido-beta-D-galactose-4-sulphuric acid	Generator
2-Deoxy-2-acetamido-β-D-galactose-4-sulfate	Generator
2-Deoxy-2-acetamido-β-D-galactose-4-sulfuric acid	Generator
2-Deoxy-2-acetamido-β-D-galactose-4-sulphate	Generator
2-Deoxy-2-acetamido-β-D-galactose-4-sulphuric acid	Generator
b-D-GalpNAc4S	Generator
Β-D-galpnac4S	Generator
N-Acetylgalactosamine 4-sulfate	Generator
N-Acetylgalactosamine 4-sulfuric acid	Generator
N-Acetylgalactosamine 4-sulphuric acid	Generator
2-(Acetylamino)-2-deoxy-D-galactose 4-(hydrogen sulfate)	HMDB
2-(Acetylamino)-2-deoxy-D-galactose 4-(hydrogen sulphate)	HMDB
GalNAc4S	HMDB
N-Acetyl-D-galactosamine 4-sulfate	HMDB
N-Acetyl-D-galactosamine 4-sulphate	HMDB
N-Acetylgalactosamine-4-sulfate	HMDB
N-Acetylgalactosamine-4-sulphate	HMDB
NAG-4-S	HMDB
N-[(2R,3R,4R,5R,6R)-2,4-Dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-3-yl]ethanimidate	HMDB
N-[(2R,3R,4R,5R,6R)-2,4-Dihydroxy-6-(hydroxymethyl)-5-(sulphooxy)oxan-3-yl]ethanimidate	HMDB
N-[(2R,3R,4R,5R,6R)-2,4-Dihydroxy-6-(hydroxymethyl)-5-(sulphooxy)oxan-3-yl]ethanimidic acid	HMDB

Chemical Formula

C₈H₁₅NO₉S

Average Mass

301.2710 Da

Monoisotopic Mass

301.04675 Da

IUPAC Name

[(2R,3R,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid

Traditional Name

[(2R,3R,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid

CAS Registry Number

45233-43-0

SMILES

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

InChI Identifier

InChI=1S/C8H15NO9S/c1-3(11)9-5-6(12)7(18-19(14,15)16)4(2-10)17-8(5)13/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H,14,15,16)/t4-,5-,6-,7+,8-/m1/s1

InChI Key

WHCJUIFHMJFEFZ-UIAUGNHASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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

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 sulfate
Monosaccharide
Oxane
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Acetamide
Carboxamide group
Hemiacetal
Secondary alcohol
Secondary carboxylic acid amide
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic nitrogen compound
Primary alcohol
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	42.9 g/L	ALOGPS
logP	-2	ALOGPS
logP	-4.9	ChemAxon
logS	-0.85	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.62 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.02 m³·mol⁻¹	ChemAxon
Polarizability	25.95 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

HMDB0000781

DrugBank ID

DB01872

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022238

KNApSAcK ID

Not Available

Chemspider ID

393546

KEGG Compound ID

C16265

BioCyc ID

CPD-12516

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5747

PubChem Compound

446101

PDB ID

Not Available

ChEBI ID

44391

Good Scents ID

Not Available

References

General References

Hopwood JJ, Elliott H: Urinary excretion of sulphated N-acetylhexosamines in patients with various mucopolysaccharidoses. Biochem J. 1985 Aug 1;229(3):579-86. [PubMed:3931626 ]
Takagaki K, Munakata H, Majima M, Endo M: Enzymatic reconstruction of a hybrid glycosaminoglycan containing 6-sulfated, 4-sulfated, and unsulfated N-acetylgalactosamine. Biochem Biophys Res Commun. 1999 May 19;258(3):741-4. doi: 10.1006/bbrc.1999.0697. [PubMed:10329456 ]
Kotlo K, Bhattacharyya S, Yang B, Feferman L, Tejaskumar S, Linhardt R, Danziger R, Tobacman JK: Impact of salt exposure on N-acetylgalactosamine-4-sulfatase (arylsulfatase B) activity, glycosaminoglycans, kininogen, and bradykinin. Glycoconj J. 2013 Oct;30(7):667-76. doi: 10.1007/s10719-013-9468-8. Epub 2013 Feb 6. [PubMed:23385884 ]
Ustyuzhanina NE, Bilan MI, Dmitrenok AS, Nifantiev NE, Usov AI: Fucosylated chondroitin sulfates from the sea cucumbers Holothuria tubulosa and Holothuria stellati. Carbohydr Polym. 2018 Nov 15;200:1-5. doi: 10.1016/j.carbpol.2018.07.035. Epub 2018 Jul 26. [PubMed:30177144 ]

Showing NP-Card for N-Acetylgalactosamine 4-sulphate (NP0001155)

MOL for NP0001155 (N-Acetylgalactosamine 4-sulphate)

3D MOL for NP0001155 (N-Acetylgalactosamine 4-sulphate)

3D SDF for NP0001155 (N-Acetylgalactosamine 4-sulphate)

3D-SDF for NP0001155 (N-Acetylgalactosamine 4-sulphate)

PDB for NP0001155 (N-Acetylgalactosamine 4-sulphate)

3D PDB for NP0001155 (N-Acetylgalactosamine 4-sulphate)

SMILES for NP0001155 (N-Acetylgalactosamine 4-sulphate)

INCHI for NP0001155 (N-Acetylgalactosamine 4-sulphate)

Structure for NP0001155 (N-Acetylgalactosamine 4-sulphate)

3D Structure for NP0001155 (N-Acetylgalactosamine 4-sulphate)