NP-MRD: Showing NP-Card for Glucosamine 6-phosphate (NP0001436)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-06-29 00:46:56 UTC

NP-MRD ID

NP0001436

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glucosamine 6-phosphate

Description

Glucosamine 6-phosphate (CAS: 3616-42-0) Is normally produced in endothelial cells via de novo glucosamine synthesis by the enzyme fructose-6-phosphate amidotransferase and the modulation of this pathway by hyperglycemia and glutamine. Glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines in mammals.It is a member of the N-terminal nucleophile class of amidotransferases, GFAT transfers the amino group from the L-glutamine amide to D-fructose 6-phosphate, producing glutamic acid and glucosamine 6-phosphate. As glucosamine inhibits endothelial nitric oxide synthesis it has important implications for impaired endothelium-dependent relaxation and vascular dysfunction in diabetes mellitus (PMID: 11270676 , 11842094 ).

Structure

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

HMDB0001254
     RDKit          3D
Glucosamine 6-phosphate
 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.5173    0.9906    0.4241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433    0.6812    0.1385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3114    0.5107    1.3889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1752   -0.0696    2.3421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2667   -0.3164    1.2686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3349   -0.5206    0.0597 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4562    0.5021   -0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5478   -0.1151   -0.7126 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8741   -0.1364    0.3500 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.6093   -1.1416    1.4694 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2268   -0.6539   -0.5092 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2126    1.3713    0.9992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5617   -0.6329   -1.1073 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3022   -1.7285   -1.9280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961   -0.6448   -0.6113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9268   -0.7829   -1.6120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0748    0.7040   -0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5715    2.0253    0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730    1.4667   -0.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0768    1.5250    1.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0106   -1.0528    2.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870   -1.5018    0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7182    1.0573    0.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0755    1.2519   -0.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3656    0.0641   -1.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330    2.0811    0.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4512    0.2880   -1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3882   -2.5417   -1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0672   -1.4562    0.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7269   -1.2243   -1.2040 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  1  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  6
  3 20  1  1
  4 21  1  0
  6 22  1  1
  7 23  1  0
  7 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  6
 14 28  1  0
 15 29  1  1
 16 30  1  0
M  END


  Mrv1652307172022512D          

 16 16  0  0  0  0            999 V2000
 9999.5865 9999.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5865 9998.2735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0150 9997.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4446 9999.9236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4480 9998.2712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.7300 9999.5110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.7300 9998.6860    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0154 9998.2735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3010 9998.6860    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3009 9999.5110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.0155 9999.9236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8719 9999.5106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1580 9999.9241    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9998.570610000.6384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4420 9999.5106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.745310000.6384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  0  0  0  0
 10 11  1  0  0  0  0
 10  1  1  1  0  0  0
  9  2  1  6  0  0  0
  8  3  1  1  0  0  0
  6  4  1  6  0  0  0
  7  5  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
  1 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001436

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1

> <INCHI_KEY>
XHMJOUIAFHJHBW-UKFBFLRUSA-N

> <FORMULA>
C6H14NO8P

> <MOLECULAR_WEIGHT>
259.151

> <EXACT_MASS>
259.045702941

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.419863006161435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.60

> <JCHEM_LOGP>
-4.1756722937241015

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.244475918446593

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2231700437457214

> <JCHEM_PKA_STRONGEST_BASIC>
8.234242859039174

> <JCHEM_POLAR_SURFACE_AREA>
162.70000000000002

> <JCHEM_REFRACTIVITY>
48.453799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.48e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-D-glucosamine 6-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001254
     RDKit          3D
Glucosamine 6-phosphate
 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.5173    0.9906    0.4241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433    0.6812    0.1385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3114    0.5107    1.3889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1752   -0.0696    2.3421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2667   -0.3164    1.2686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3349   -0.5206    0.0597 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4562    0.5021   -0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5478   -0.1151   -0.7126 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8741   -0.1364    0.3500 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.6093   -1.1416    1.4694 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2268   -0.6539   -0.5092 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2126    1.3713    0.9992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5617   -0.6329   -1.1073 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3022   -1.7285   -1.9280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961   -0.6448   -0.6113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9268   -0.7829   -1.6120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0748    0.7040   -0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5715    2.0253    0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730    1.4667   -0.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0768    1.5250    1.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0106   -1.0528    2.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870   -1.5018    0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7182    1.0573    0.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0755    1.2519   -0.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3656    0.0641   -1.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330    2.0811    0.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4512    0.2880   -1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3882   -2.5417   -1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0672   -1.4562    0.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7269   -1.2243   -1.2040 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  1  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  6
  3 20  1  1
  4 21  1  0
  6 22  1  1
  7 23  1  0
  7 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  6
 14 28  1  0
 15 29  1  1
 16 30  1  0
M  END

HEADER    PROTEIN                                 17-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-20         0                                  
HETATM    1  C   UNK     0    8665.8958666.523   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8665.8958663.444   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8668.5618661.904   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8671.2308666.524   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0    8671.2368663.440   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8669.8968665.754   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8669.8968664.214   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.5628663.444   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8667.2298664.214   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.2288665.754   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8668.5628666.524   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8664.5618665.753   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0    8663.2288666.525   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0    8663.9988667.858   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8661.8928665.753   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8662.4588667.858   0.000  0.00  0.00           O+0
CONECT    1   10   12                                                       
CONECT    2    9                                                            
CONECT    3    8                                                            
CONECT    4    6                                                            
CONECT    5    7                                                            
CONECT    6    7   11    4                                                  
CONECT    7    6    8    5                                                  
CONECT    8    7    9    3                                                  
CONECT    9    8   10    2                                                  
CONECT   10    9   11    1                                                  
CONECT   11    6   10                                                       
CONECT   12   13    1                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0001254
HETATM    1  N1  UNL     1      -3.517   0.991   0.424  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.143   0.681   0.139  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.311   0.511   1.389  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.175  -0.070   2.342  1.00  0.00           O  
HETATM    5  O2  UNL     1      -0.267  -0.316   1.269  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.335  -0.521   0.060  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.456   0.502  -0.085  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.548  -0.115  -0.713  1.00  0.00           O  
HETATM    9  P1  UNL     1       3.874  -0.136   0.350  1.00  0.00           P  
HETATM   10  O4  UNL     1       3.609  -1.142   1.469  1.00  0.00           O  
HETATM   11  O5  UNL     1       5.227  -0.654  -0.509  1.00  0.00           O  
HETATM   12  O6  UNL     1       4.213   1.371   0.999  1.00  0.00           O  
HETATM   13  C5  UNL     1      -0.562  -0.633  -1.107  1.00  0.00           C  
HETATM   14  O7  UNL     1      -0.302  -1.728  -1.928  1.00  0.00           O  
HETATM   15  C6  UNL     1      -1.996  -0.645  -0.611  1.00  0.00           C  
HETATM   16  O8  UNL     1      -2.927  -0.783  -1.612  1.00  0.00           O  
HETATM   17  H1  UNL     1      -4.075   0.704  -0.405  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.571   2.025   0.536  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.673   1.467  -0.490  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.077   1.525   1.792  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.011  -1.053   2.416  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.887  -1.502   0.146  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.718   1.057   0.773  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.076   1.252  -0.864  1.00  0.00           H  
HETATM   25  H9  UNL     1       5.366   0.064  -1.202  1.00  0.00           H  
HETATM   26  H10 UNL     1       3.933   2.081   0.364  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.451   0.288  -1.720  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.388  -2.542  -1.359  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.067  -1.456   0.147  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.727  -1.224  -1.204  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   12
CONECT   11   25
CONECT   12   26
CONECT   13   14   15   27
CONECT   14   28
CONECT   15   16   29
CONECT   16   30
END

HMDB0001254
     RDKit          3D
Glucosamine 6-phosphate
 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.5173    0.9906    0.4241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433    0.6812    0.1385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3114    0.5107    1.3889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1752   -0.0696    2.3421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2667   -0.3164    1.2686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3349   -0.5206    0.0597 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4562    0.5021   -0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5478   -0.1151   -0.7126 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8741   -0.1364    0.3500 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.6093   -1.1416    1.4694 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2268   -0.6539   -0.5092 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2126    1.3713    0.9992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5617   -0.6329   -1.1073 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3022   -1.7285   -1.9280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961   -0.6448   -0.6113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9268   -0.7829   -1.6120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0748    0.7040   -0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5715    2.0253    0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730    1.4667   -0.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0768    1.5250    1.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0106   -1.0528    2.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870   -1.5018    0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7182    1.0573    0.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0755    1.2519   -0.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3656    0.0641   -1.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330    2.0811    0.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4512    0.2880   -1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3882   -2.5417   -1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0672   -1.4562    0.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7269   -1.2243   -1.2040 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  1  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  6
  3 20  1  1
  4 21  1  0
  6 22  1  1
  7 23  1  0
  7 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  6
 14 28  1  0
 15 29  1  1
 16 30  1  0
M  END

View in JSmol

Synonyms

Value	Source
2-Amino-2-deoxy-6-O-phosphono-alpha-D-glucopyranose	ChEBI
alpha-D-Glucosamine 6-(dihydrogen phosphate)	ChEBI
2-Amino-2-deoxy-6-O-phosphono-a-D-glucopyranose	Generator
2-Amino-2-deoxy-6-O-phosphono-α-D-glucopyranose	Generator
a-D-Glucosamine 6-(dihydrogen phosphate)	Generator
a-D-Glucosamine 6-(dihydrogen phosphoric acid)	Generator
alpha-D-Glucosamine 6-(dihydrogen phosphoric acid)	Generator
Α-D-glucosamine 6-(dihydrogen phosphate)	Generator
Α-D-glucosamine 6-(dihydrogen phosphoric acid)	Generator
Glucosamine 6-phosphoric acid	Generator
2-Amino-2-deoxy-D-glucose 6-phosphate	HMDB
2-Amino-2-deoxyglucose 6-phosphate	HMDB
2-Amino-D-glucose-6-phosphate	HMDB
D-Glucosamine 6-phosphate	HMDB
D-Glucosamine phosphate	HMDB
D-Glucosamine-6-phosphate	HMDB
Glucosamine 6 -phosphate	HMDB
Glucosamine-6-p	HMDB
Glucosamine-6-phosphate	HMDB
Glucose-6-phosphorate	HMDB
Glucose-6-phosphoric acid	HMDB
Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester	HMDB
GLCN-6-p	HMDB

Chemical Formula

C₆H₁₄NO₈P

Average Mass

259.1510 Da

Monoisotopic Mass

259.04570 Da

IUPAC Name

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

Traditional Name

α-D-glucosamine 6-phosphate

CAS Registry Number

3616-42-0

SMILES

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

InChI Identifier

InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1

InChI Key

XHMJOUIAFHJHBW-UKFBFLRUSA-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

Species Where Detected

Species Name	Source	Reference
Escherichia coli	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexose phosphates

Alternative Parents

Substituents

Hexose phosphate
Monosaccharide phosphate
Amino saccharide
Monoalkyl phosphate
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Hemiacetal
1,2-diol
Secondary alcohol
1,2-aminoalcohol
Organoheterocyclic compound
Oxacycle
Polyol
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic nitrogen compound
Organic oxide
Amine
Primary amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

2-amino-2-deoxy-D-glucopyranose 6-phosphate (CHEBI:15873 )

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	34.8 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-4.2	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	8.23	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	162.7 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.45 m³·mol⁻¹	ChemAxon
Polarizability	21.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001254

DrugBank ID

DB02657

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

6111

PubChem Compound

439217

PDB ID

Not Available

ChEBI ID

15873

Good Scents ID

Not Available

References

General References

Wu G, Haynes TE, Yan W, Meininger CJ: Presence of glutamine:fructose-6-phosphate amidotransferase for glucosamine-6-phosphate synthesis in endothelial cells: effects of hyperglycaemia and glutamine. Diabetologia. 2001 Feb;44(2):196-202. [PubMed:11270676 ]
Broschat KO, Gorka C, Page JD, Martin-Berger CL, Davies MS, Huang Hc HC, Gulve EA, Salsgiver WJ, Kasten TP: Kinetic characterization of human glutamine-fructose-6-phosphate amidotransferase I: potent feedback inhibition by glucosamine 6-phosphate. J Biol Chem. 2002 Apr 26;277(17):14764-70. Epub 2002 Feb 12. [PubMed:11842094 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
Furchak JR, Yang P, Jennings C, Walter NG, Kennedy RT: Assay for glucosamine 6-phosphate using a ligand-activated ribozyme with fluorescence resonance energy transfer or CE-laser-induced fluorescence detection. Anal Chem. 2008 Nov 1;80(21):8195-201. doi: 10.1021/ac801410k. Epub 2008 Oct 9. [PubMed:18842060 ]

Showing NP-Card for Glucosamine 6-phosphate (NP0001436)

MOL for NP0001436 (Glucosamine 6-phosphate)

3D MOL for NP0001436 (Glucosamine 6-phosphate)

3D SDF for NP0001436 (Glucosamine 6-phosphate)

3D-SDF for NP0001436 (Glucosamine 6-phosphate)

PDB for NP0001436 (Glucosamine 6-phosphate)

3D PDB for NP0001436 (Glucosamine 6-phosphate)

SMILES for NP0001436 (Glucosamine 6-phosphate)

INCHI for NP0001436 (Glucosamine 6-phosphate)

Structure for NP0001436 (Glucosamine 6-phosphate)

3D Structure for NP0001436 (Glucosamine 6-phosphate)