NP-MRD: Showing NP-Card for Glucosamine 6-sulfate (NP0000655)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:17:13 UTC

NP-MRD ID

NP0000655

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glucosamine 6-sulfate

Description

Glucosamine 6-sulfate is a naturally occurring compound present in many of the body's tissues, and belongs to a class of compounds known as glycosaminoglycans (GAGs). Glucosamine 6-sulfate is being used in the treatment of arthritis. Glucosamine for arthritis products is usually formulated as the hydrochloride salt or glucosamine sulfate and often combined with chondroitin sulphate. It is notable that while both the hydrochloride salt and glucosamine sulfate are used in pharmaceutical preparations, glucosamine sulfate is thought to have a higher biological activity due to the presence of the sulfate. It should also be noted that there is a large cost difference between the two salts, with the hydrochloride salt being significantly less expensive. (PMID: 15925239 ).

Structure

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

HMDB0000592
     RDKit          3D
Glucosamine 6-sulfate
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.5123    0.9920   -0.7273 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110   -0.1067    0.1976 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5888   -1.2075   -0.5487 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3098   -2.2080    0.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4423   -0.8079   -1.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0630    0.4154   -0.9068 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5835    0.2412   -0.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8043   -0.9234   -0.1878 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3762   -1.1351    0.3002 S   0  0  0  0  0  6  0  0  0  0  0  0
    4.2062   -1.5471   -0.8917 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -2.3024    1.2636 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0349    0.2137    1.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2697    1.1124    0.3586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8480    2.3773    0.1588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759    0.3563    1.2205 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5760   -0.7063    1.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6776    0.6882   -1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2204    1.6558   -0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2336   -0.4644    0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3040   -1.6863   -1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1399   -2.4609    0.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165    1.0921   -1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872    1.1249   -0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8902    0.1238   -1.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5895    0.6759    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6046    1.2996    1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5407    2.8116   -0.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529    0.9992    1.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099   -0.6235    2.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
  6 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  2  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  6
  4 21  1  0
  6 22  1  6
  7 23  1  0
  7 24  1  0
 12 25  1  0
 13 26  1  1
 14 27  1  0
 15 28  1  1
 16 29  1  0
M  END


  Mrv1652305271900132D          

 16 16  0  0  1  0            999 V2000
   23.7357  -12.2258    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.7357   -9.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5922  -10.1632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5922   -8.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4501   -8.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7357  -11.4008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7357  -13.0508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5607  -12.2258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9107  -12.2258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0212   -7.6882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3067   -8.9257    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.3067   -9.7507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.0212   -8.5132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.0212  -10.1632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.7357   -8.9257    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.0212  -10.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  2  0  0  0  0
  1  9  2  0  0  0  0
  2 14  1  0  0  0  0
  2 15  1  0  0  0  0
 12  3  1  1  0  0  0
 11  4  1  6  0  0  0
 15  5  1  6  0  0  0
  6 16  1  0  0  0  0
 13 10  1  1  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0000655

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H13NO8S/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H,11,12,13)/t2-,3-,4-,5-,6-/m1/s1

> <INCHI_KEY>
MTDHILKWIRSIHB-QZABAPFNSA-N

> <FORMULA>
C6H13NO8S

> <MOLECULAR_WEIGHT>
259.234

> <EXACT_MASS>
259.036187087

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.375918668402807

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R,6R)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}sulfonic acid

> <ALOGPS_LOGP>
-2.30

> <JCHEM_LOGP>
-3.9939593449410413

> <ALOGPS_LOGS>
-0.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.727468589260997

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.8795458232818172

> <JCHEM_PKA_STRONGEST_BASIC>
8.229727115001346

> <JCHEM_POLAR_SURFACE_AREA>
159.54000000000002

> <JCHEM_REFRACTIVITY>
47.57270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glucosamine 6-sulfate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000592
     RDKit          3D
Glucosamine 6-sulfate
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.5123    0.9920   -0.7273 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110   -0.1067    0.1976 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5888   -1.2075   -0.5487 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3098   -2.2080    0.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4423   -0.8079   -1.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0630    0.4154   -0.9068 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5835    0.2412   -0.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8043   -0.9234   -0.1878 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3762   -1.1351    0.3002 S   0  0  0  0  0  6  0  0  0  0  0  0
    4.2062   -1.5471   -0.8917 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -2.3024    1.2636 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0349    0.2137    1.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2697    1.1124    0.3586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8480    2.3773    0.1588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759    0.3563    1.2205 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5760   -0.7063    1.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6776    0.6882   -1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2204    1.6558   -0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2336   -0.4644    0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3040   -1.6863   -1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1399   -2.4609    0.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165    1.0921   -1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872    1.1249   -0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8902    0.1238   -1.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5895    0.6759    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6046    1.2996    1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5407    2.8116   -0.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529    0.9992    1.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099   -0.6235    2.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
  6 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  2  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  6
  4 21  1  0
  6 22  1  6
  7 23  1  0
  7 24  1  0
 12 25  1  0
 13 26  1  1
 14 27  1  0
 15 28  1  1
 16 29  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  S   UNK     0      44.307 -22.821   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      44.307 -18.201   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      40.305 -18.971   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      40.305 -15.891   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      45.640 -15.891   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      44.307 -21.281   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      44.307 -24.361   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      45.847 -22.821   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      42.767 -22.821   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      42.973 -14.351   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      41.639 -16.661   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      41.639 -18.201   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      42.973 -15.891   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      42.973 -18.971   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      44.307 -16.661   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      42.973 -20.511   0.000  0.00  0.00           C+0
CONECT    1    6    7    8    9                                             
CONECT    2   14   15                                                       
CONECT    3   12                                                            
CONECT    4   11                                                            
CONECT    5   15                                                            
CONECT    6    1   16                                                       
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9    1                                                            
CONECT   10   13                                                            
CONECT   11    4   12   13                                                  
CONECT   12    3   11   14                                                  
CONECT   13   10   11   15                                                  
CONECT   14    2   12   16                                                  
CONECT   15    2    5   13                                                  
CONECT   16    6   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0000592
HETATM    1  N1  UNL     1      -2.512   0.992  -0.727  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.311  -0.107   0.198  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.589  -1.207  -0.549  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.310  -2.208   0.395  1.00  0.00           O  
HETATM    5  O2  UNL     1      -0.442  -0.808  -1.138  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.063   0.415  -0.907  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.583   0.241  -0.907  1.00  0.00           C  
HETATM    8  O3  UNL     1       1.804  -0.923  -0.188  1.00  0.00           O  
HETATM    9  S1  UNL     1       3.376  -1.135   0.300  1.00  0.00           S  
HETATM   10  O4  UNL     1       4.206  -1.547  -0.892  1.00  0.00           O  
HETATM   11  O5  UNL     1       3.390  -2.302   1.264  1.00  0.00           O  
HETATM   12  O6  UNL     1       4.035   0.214   1.028  1.00  0.00           O  
HETATM   13  C5  UNL     1      -0.270   1.112   0.359  1.00  0.00           C  
HETATM   14  O7  UNL     1      -0.848   2.377   0.159  1.00  0.00           O  
HETATM   15  C6  UNL     1      -1.276   0.356   1.221  1.00  0.00           C  
HETATM   16  O8  UNL     1      -0.576  -0.706   1.773  1.00  0.00           O  
HETATM   17  H1  UNL     1      -2.678   0.688  -1.705  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.220   1.656  -0.375  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.234  -0.464   0.663  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.304  -1.686  -1.264  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.140  -2.461   0.892  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.217   1.092  -1.753  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.087   1.125  -0.497  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.890   0.124  -1.970  1.00  0.00           H  
HETATM   25  H9  UNL     1       4.589   0.676   0.359  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.605   1.300   1.031  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.541   2.812  -0.664  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.753   0.999   1.968  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.410  -0.623   2.735  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3   15   19
CONECT    3    4    5   20
CONECT    4   21
CONECT    5    6
CONECT    6    7   13   22
CONECT    7    8   23   24
CONECT    8    9
CONECT    9   10   10   11   11
CONECT    9   12
CONECT   12   25
CONECT   13   14   15   26
CONECT   14   27
CONECT   15   16   28
CONECT   16   29
END

HMDB0000592
     RDKit          3D
Glucosamine 6-sulfate
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.5123    0.9920   -0.7273 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110   -0.1067    0.1976 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5888   -1.2075   -0.5487 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3098   -2.2080    0.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4423   -0.8079   -1.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0630    0.4154   -0.9068 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5835    0.2412   -0.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8043   -0.9234   -0.1878 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3762   -1.1351    0.3002 S   0  0  0  0  0  6  0  0  0  0  0  0
    4.2062   -1.5471   -0.8917 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -2.3024    1.2636 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0349    0.2137    1.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2697    1.1124    0.3586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8480    2.3773    0.1588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759    0.3563    1.2205 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5760   -0.7063    1.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6776    0.6882   -1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2204    1.6558   -0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2336   -0.4644    0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3040   -1.6863   -1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1399   -2.4609    0.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165    1.0921   -1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872    1.1249   -0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8902    0.1238   -1.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5895    0.6759    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6046    1.2996    1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5407    2.8116   -0.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529    0.9992    1.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099   -0.6235    2.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
  6 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  2  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  6
  4 21  1  0
  6 22  1  6
  7 23  1  0
  7 24  1  0
 12 25  1  0
 13 26  1  1
 14 27  1  0
 15 28  1  1
 16 29  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-Amino-2-deoxy-beta-D-glucopyranose 6-sulfate	ChEBI
2-Amino-2-deoxy-D-glucose 6-sulfate	ChEBI
2-Amino-2-deoxy-D-glucose 6-sulphate	ChEBI
6-O-SulfO-beta-D-glucosamine	ChEBI
beta-D-Glucosamine 6-O-sulfate	ChEBI
D-Glucosamine-6-sulfate	ChEBI
D-Glucosamine-6-sulphate	ChEBI
GLCN-6S	ChEBI
Glucosamine 6-O-sulfate	ChEBI
Glucosamine 6-O-sulphate	ChEBI
Glucosamine 6-sulphate	ChEBI
2-Amino-2-deoxy-b-D-glucopyranose 6-sulfate	Generator
2-Amino-2-deoxy-b-D-glucopyranose 6-sulfuric acid	Generator
2-Amino-2-deoxy-b-D-glucopyranose 6-sulphate	Generator
2-Amino-2-deoxy-b-D-glucopyranose 6-sulphuric acid	Generator
2-Amino-2-deoxy-beta-D-glucopyranose 6-sulfuric acid	Generator
2-Amino-2-deoxy-beta-D-glucopyranose 6-sulphate	Generator
2-Amino-2-deoxy-beta-D-glucopyranose 6-sulphuric acid	Generator
2-Amino-2-deoxy-β-D-glucopyranose 6-sulfate	Generator
2-Amino-2-deoxy-β-D-glucopyranose 6-sulfuric acid	Generator
2-Amino-2-deoxy-β-D-glucopyranose 6-sulphate	Generator
2-Amino-2-deoxy-β-D-glucopyranose 6-sulphuric acid	Generator
2-Amino-2-deoxy-D-glucose 6-sulfuric acid	Generator
2-Amino-2-deoxy-D-glucose 6-sulphuric acid	Generator
6-O-SulfO-b-D-glucosamine	Generator
6-O-SulfO-β-D-glucosamine	Generator
6-O-SulphO-b-D-glucosamine	Generator
6-O-SulphO-beta-D-glucosamine	Generator
6-O-SulphO-β-D-glucosamine	Generator
b-D-Glucosamine 6-O-sulfate	Generator
b-D-Glucosamine 6-O-sulfuric acid	Generator
b-D-Glucosamine 6-O-sulphate	Generator
b-D-Glucosamine 6-O-sulphuric acid	Generator
beta-D-Glucosamine 6-O-sulfuric acid	Generator
beta-D-Glucosamine 6-O-sulphate	Generator
beta-D-Glucosamine 6-O-sulphuric acid	Generator
Β-D-glucosamine 6-O-sulfate	Generator
Β-D-glucosamine 6-O-sulfuric acid	Generator
Β-D-glucosamine 6-O-sulphate	Generator
Β-D-glucosamine 6-O-sulphuric acid	Generator
D-Glucosamine-6-sulfuric acid	Generator
D-Glucosamine-6-sulphuric acid	Generator
Glucosamine 6-O-sulfuric acid	Generator
Glucosamine 6-O-sulphuric acid	Generator
Glucosamine 6-sulfuric acid	Generator
Glucosamine 6-sulphuric acid	Generator
b-D-Glucosamine 6-sulfate	HMDB
b-D-Glucosamine 6-sulfuric acid	HMDB
b-D-Glucosamine 6-sulphate	HMDB
b-D-Glucosamine 6-sulphuric acid	HMDB
beta-D-Glucosamine 6-sulfuric acid	HMDB
beta-D-Glucosamine 6-sulphate	HMDB
beta-D-Glucosamine 6-sulphuric acid	HMDB
Β-D-glucosamine 6-sulfate	HMDB
Β-D-glucosamine 6-sulfuric acid	HMDB
Β-D-glucosamine 6-sulphate	HMDB
Β-D-glucosamine 6-sulphuric acid	HMDB
Glucosamine 6-sulfate	Generator

Chemical Formula

C₆H₁₃NO₈S

Average Mass

259.2340 Da

Monoisotopic Mass

259.03619 Da

IUPAC Name

{[(2R,3S,4R,5R,6R)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}sulfonic acid

Traditional Name

glucosamine 6-sulfate

CAS Registry Number

91674-26-9

SMILES

N[C@H]1[C@H](O)O[C@H](COS(O)(=O)=O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C6H13NO8S/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H,11,12,13)/t2-,3-,4-,5-,6-/m1/s1

InChI Key

MTDHILKWIRSIHB-QZABAPFNSA-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	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
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	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 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	¹H NMR Spectrum (1D, 300 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	¹H NMR Spectrum (1D, 400 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	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 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	¹H NMR Spectrum (1D, 700 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	¹H NMR Spectrum (1D, 800 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	¹H NMR Spectrum (1D, 900 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 hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Monosaccharide sulfate
Amino saccharide
Oxane
Sulfuric acid monoester
Sulfate-ester
Alkyl sulfate
Sulfuric acid ester
Organic sulfuric acid or derivatives
Hemiacetal
1,2-diol
Secondary alcohol
1,2-aminoalcohol
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organonitrogen compound
Primary amine
Primary aliphatic amine
Organic nitrogen compound
Alcohol
Amine
Organopnictogen compound
Organic oxide
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	129 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-4	ChemAxon
logS	-0.3	ALOGPS
pKa (Strongest Acidic)	-1.9	ChemAxon
pKa (Strongest Basic)	8.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	159.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.57 m³·mol⁻¹	ChemAxon
Polarizability	22.38 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

HMDB0000592

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022132

KNApSAcK ID

Not Available

Chemspider ID

65298

KEGG Compound ID

C04132

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5571

PubChem Compound

72361

PDB ID

Not Available

ChEBI ID

133343

Good Scents ID

Not Available

References

General References

Skelton TP, Hooper LV, Srivastava V, Hindsgaul O, Baenziger JU: Characterization of a sulfotransferase responsible for the 4-O-sulfation of terminal beta-N-acetyl-D-galactosamine on asparagine-linked oligosaccharides of glycoprotein hormones. J Biol Chem. 1991 Sep 15;266(26):17142-50. [PubMed:1894609 ]
Lindahl B, Westling C, Gimenez-Gallego G, Lindahl U, Salmivirta M: Common binding sites for beta-amyloid fibrils and fibroblast growth factor-2 in heparan sulfate from human cerebral cortex. J Biol Chem. 1999 Oct 22;274(43):30631-5. [PubMed:10521448 ]
Ishihara K, Kameyama J, Hotta K: Development of an HPLC method to estimate hexosamines and its application to determine mucin content in rat and human gastric mucosa. Comp Biochem Physiol B. 1993 Apr;104(4):781-6. [PubMed:8472545 ]
Ishihara M, Takano R, Kanda T, Hayashi K, Hara S, Kikuchi H, Yoshida K: Importance of 6-O-sulfate groups of glucosamine residues in heparin for activation of FGF-1 and FGF-2. J Biochem. 1995 Dec;118(6):1255-60. [PubMed:8720143 ]
Maldonado M, Weerasinghe G, Ambroise F, Yamoah E, Londono M, Pelayo JC, Grigorian M, Oppenheimer SB: The charged milieu: a major player in fertilization reactions. Acta Histochem. 2004 Feb;106(1):3-10. [PubMed:15032323 ]
Ramsay SL, Meikle PJ, Hopwood JJ: Determination of monosaccharides and disaccharides in mucopolysaccharidoses patients by electrospray ionisation mass spectrometry. Mol Genet Metab. 2003 Mar;78(3):193-204. [PubMed:12649064 ]
Foot M, Mulholland M: Classification of chondroitin sulfate A, chondroitin sulfate C, glucosamine hydrochloride and glucosamine 6 sulfate using chemometric techniques. J Pharm Biomed Anal. 2005 Jul 1;38(3):397-407. [PubMed:15925239 ]
Kashige N, Yamaguchi T, Ohtakara A, Mitsutomi M, Brimacombe JS, Miake F, Watanabe K: Structure-activity relationships in the induction of single-strand breakage in plasmid pBR322 DNA by amino sugars and derivatives. Carbohydr Res. 1994 May 5;257(2):285-91. [PubMed:8013009 ]
Bame KJ, Lidholt K, Lindahl U, Esko JD: Biosynthesis of heparan sulfate. Coordination of polymer-modification reactions in a Chinese hamster ovary cell mutant defective in N-sulfotransferase. J Biol Chem. 1991 Jun 5;266(16):10287-93. [PubMed:2037581 ]
Maccarana M, Sakura Y, Tawada A, Yoshida K, Lindahl U: Domain structure of heparan sulfates from bovine organs. J Biol Chem. 1996 Jul 26;271(30):17804-10. [PubMed:8663266 ]
Bruce JS, McLean MW, Williamson FB, Long WF: Flavobacterium heparinum 6-O-sulphatase for N-substituted glucosamine 6-O-sulphate. Eur J Biochem. 1985 Oct 1;152(1):75-82. [PubMed:4043087 ]
Bagasra O, Whittle P, Heins B, Pomerantz RJ: Anti-human immunodeficiency virus type 1 activity of sulfated monosaccharides: comparison with sulfated polysaccharides and other polyions. J Infect Dis. 1991 Dec;164(6):1082-90. [PubMed:1720153 ]
Yagita M, Nakajima M, Saksela E: Suppression of human natural killer cell activity by amino sugars. Cell Immunol. 1989 Aug;122(1):83-95. [PubMed:2752431 ]
Salmivirta M, Safaiyan F, Prydz K, Andresen MS, Aryan M, Kolset SO: Differentiation-associated modulation of heparan sulfate structure and function in CaCo-2 colon carcinoma cells. Glycobiology. 1998 Oct;8(10):1029-36. [PubMed:9719684 ]
Petitou M, Duchaussoy P, Lederman I, Choay J, Sinay P: Binding of heparin to antithrombin III: a chemical proof of the critical role played by a 3-sulfated 2-amino-2-deoxy-D-glucose residue. Carbohydr Res. 1988 Aug 15;179:163-72. [PubMed:3208245 ]
(). Bourhill, G., Mansour, K., Perry, Kelly J., Khundkar, L., Sleva, Edward T., Kern, R., Perry, Joseph W., Williams, Ian D., Kurtz, Stewart K. Second-order nonlinear optical properties of saccharide materials. Proceedings of SPIE-The International Society for Optical Engineering (1993), 1853(Organic and Biological Optoelectronics), 110-25. .
(). O'Shea, Thomas J., Lunte, Susan M., LaCourse, William R. Detection of carbohydrates by capillary electrophoresis with pulsed amperometric detection. Analytical Chemistry (1993), 65(7), 948-51. .
(). Dallinga, Jan W., Rinkema, Fedde D., Heerma, Wigger. Fast atom bombardment mass spectrometry of some aminoglucoses and glucosamine phosphates and sulfates. Biomedical & Environmental Mass Spectrometry (1989), 18(4), 241-6. .
(). Amar, M., Dumeirain, F., Barre, A., Chatelain, C., Rouge, P. Interaction of legume lectins with sulfated and phosphorylated monosaccharides. Lectins: Biology, Biochemistry, Clinical Biochemistry (1997), 11 33-38. .
(). Saito, T., Noguchi, J., Komatsu, Kiroku. The esterification of carbohydrates in concentrated sul-furic acid. III. The synthesis of 2-amino-2-deoxy-D-glucose O-sulfate, 2-acetamido-2-deoxy-D-glucose-6-sulfate and its calcium and barium salts. Nippon Kagaku Zasshi (1961), 82 472-4. .
(). Bourhill, G., Mansour, K., Perry, Kelly J., Khundkar, L., Sleva, Edward T., Kern, R., Perry, Joseph W., Williams, Ian D., Kurtz, Stewart K. Powder second harmonic generation efficiencies of saccharide materials. Chemistry of Materials (1993), 5(6), 802-8. .

Showing NP-Card for Glucosamine 6-sulfate (NP0000655)

MOL for NP0000655 (Glucosamine 6-sulfate)

3D MOL for NP0000655 (Glucosamine 6-sulfate)

3D SDF for NP0000655 (Glucosamine 6-sulfate)

3D-SDF for NP0000655 (Glucosamine 6-sulfate)

PDB for NP0000655 (Glucosamine 6-sulfate)

3D PDB for NP0000655 (Glucosamine 6-sulfate)

SMILES for NP0000655 (Glucosamine 6-sulfate)

INCHI for NP0000655 (Glucosamine 6-sulfate)

Structure for NP0000655 (Glucosamine 6-sulfate)

3D Structure for NP0000655 (Glucosamine 6-sulfate)