MiMeDB: Showing metabocard for Glucosamine 6-phosphate (MMDBc0029600)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:33:55 UTC

Update Date

2022-08-31 13:58:51 UTC

Metabolite ID

MMDBc0029600

Metabolite Identification

Common Name

Glucosamine 6-phosphate

Description

Glucosamine 6-phosphate is normally produced via the de novo glucosamine synthesis by the enzyme fructose-6-phosphate amidotransferase and the modulation of this pathway by glutamine. Glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines. 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. (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>
MMDBc0029600

> <DATABASE_NAME>
MIME

> <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

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
Glucosamine 6-phosphoric acid	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
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	MeSH, HMDB

Molecular Formula

C₆H₁₄NO₈P

Average Mass

259.151

Monoisotopic Mass

259.045702941

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

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052b-9320000000-54466a568e39d51598c7	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0ik9-3912400000-c198d10e982d681785ed	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0970000000-095ba413dfd29c80b445	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-053r-9500000000-e4e82ba86236d6046d0d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-bd232a0933f76298e943	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-03di-0190000000-778d1a36aaf5c9b3c846	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-08i0-1690000000-f08f9e49e698f1aa134d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-002b-9010000000-8a6a96ec67621a842ce8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-002b-9010000000-8a6a96ec67621a842ce8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0190000000-280711606909adbb8814	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-08i0-1690000000-f08f9e49e698f1aa134d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03di-3190000000-0f9d6942fba86f12422e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03fr-2790000000-7fe42a3d5900a5984d04	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0490000000-818ec0fe39e531f561a4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-9850000000-40bb2cfef099c426fcbf	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kmj-9500000000-9bb59bf1855e5fa76305	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0699-8950000000-68f380f4fab22160c728	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9110000000-4f7a2c18e5b29f9e6076	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-6fc65d9a14f58d847a4f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0790000000-d9873144345380710376	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9810000000-32a2cffa4a376910fdb3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ot-9000000000-7be390edddedcba28a23	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-054k-9040000000-fd7b28df2dbc578cfc0b	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9010000000-f0f082b70bb688bd4b38	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Lysosome

Biospecimen Locations

Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191726	Glucosamine 6-phosphate N-acetyltransferase	Enzyme	Q96EK6	Homo sapiens
MMDBp0191880	Glucokinase	Enzyme	P35557	Homo sapiens
MMDBp0191881	Glucosamine-6-phosphate isomerase 1	Unknown	P46926	Homo sapiens
MMDBp0191882	Hexokinase-3	Enzyme	P52790	Homo sapiens
MMDBp0191883	Hexokinase-2	Enzyme	P52789	Homo sapiens
MMDBp0191884	Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2	Enzyme	O94808	Homo sapiens
MMDBp0191885	Hexokinase-1	Enzyme	P19367	Homo sapiens
MMDBp0191886	Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1	Enzyme	Q06210	Homo sapiens
MMDBp0193927	Putative N-acetylglucosamine-6-phosphate deacetylase	Enzyme	Q9Y303	Homo sapiens
MMDBp0196018	Glucosamine-6-phosphate isomerase 2	Enzyme	Q8TDQ7	Homo sapiens
MMDBp0196842	Putative hexokinase HKDC1	Unknown	Q2TB90

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000174	Acetyl-CoA	N-Acetyl-D-Glucosamine 6-Phosphate	Not Available	N-Acetylglucosamine-6-Phosphate Synthase	VMH	30371894
MMDBr0001428	Adenosine triphosphate	ADP	Not Available	Hexokinase (D-Glucosamine:ATP)	VMH	30371894
MMDBr0002521	Glucosamine	Glucosamine 6-phosphate	Hexokinase 1	Hexokinase	VMH	30371894
MMDBr0002522	Deoxyadenosine triphosphate	dADP	Hexokinase 1	Hexokinase	VMH	30371894
MMDBr0006938	Glucosamine	Glucosamine 6-phosphate	Not Available	D-glucosamine transport via PEP:Pyr PTS	VMH	30371894
MMDBr0007424	Fructose 6-phosphate	Glucosamine 6-phosphate	Not Available	Glutamine-Fructose-6-Phosphate Transaminase	VMH	30371894
MMDBr0007519	D-Glucosamine 1-phosphate	Glucosamine 6-phosphate	Not Available	Phosphoglucosamine mutase	VMH	30371894
MMDBr0007703	N-Acetyl-D-Glucosamine 6-Phosphate	Acetic acid	Not Available	N-Acetylglucosamine-6-Phosphate Deacetylase	VMH	30371894
MMDBr0007819	Glucosamine 6-phosphate	Fructose 6-phosphate	Not Available	Glucosamine-6-Phosphate Deaminase	VMH	30371894
MMDBr0013088	Glucosamine 6-phosphate	beta-D-Fructose 6-phosphate	D-galactosamine-6-phosphate deaminase AgaS	Deamination; Isomerization	RHEA	34755880
MMDBr0018434	Water	Acetic acid	N-acetylglucosamine-6-phosphate deacetylase	Deacetylation	PathBank	31602464
MMDBr0018435	Water	Ammonium	Glucosamine-6-phosphate deaminase	Deamination	PathBank	31602464
MMDBr0018436	L-Glutamine	L-Glutamic acid	Glutamine--fructose-6-phosphate aminotransferase [isomerizing]	Amine group addition	PathBank	31602464
MMDBr0018441	Glucosamine 6-phosphate	Glucosamine-1P	Phosphoglucosamine mutase	Transfer of phosphate groups within a molecule	PathBank	31602464
MMDBr0018638	L-Glutamine	L-Glutamic acid	Glutamine--fructose-6-phosphate aminotransferase [isomerizing]	Amine group addition	PathBank	31602464
MMDBr0019555	L-Glutamine	L-Glutamic acid	Glutamine--fructose-6-phosphate aminotransferase [isomerizing]	Amine group addition	PathBank	31602464
MMDBr0019556	Acetyl-CoA	Hydrogen Ion	Glucosamine 6-phosphate N-acetyltransferase	Acetylation	PathBank	31602464

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	270	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; River trout ; Chicken	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	481	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool; Catfish	Metabolic reconstruction
Bacteria	Actinobacteria	141	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	127	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	7	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	7	Human feces; Human	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown
Bacteria/NULL	Proteobacteria	1	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; River trout ; Chicken	Unknown; Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001254

DrugBank ID

DB02657

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022515

KNApSAcK ID

Not Available

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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

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. doi: 10.1007/s001250051599. [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. doi: 10.1074/jbc.M201056200. 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 ]

Showing metabocard for Glucosamine 6-phosphate (MMDBc0029600)

MOL for #<Metabolite:0x00007fe2a805b5f8>

3D MOL for #<Metabolite:0x00007fe2a805b5f8>

3D SDF for #<Metabolite:0x00007fe2a805b5f8>

3D-SDF for #<Metabolite:0x00007fe2a805b5f8>

PDB for #<Metabolite:0x00007fe2a805b5f8>

3D PDB for #<Metabolite:0x00007fe2a805b5f8>

SMILES for #<Metabolite:0x00007fe2a805b5f8>

INCHI for #<Metabolite:0x00007fe2a805b5f8>

Structure for #<Metabolite:0x00007fe2a805b5f8>

3D Structure for #<Metabolite:0x00007fe2a805b5f8>