MiMeDB: Showing metabocard for N-Acetyl-glucosamine 1-phosphate (MMDBc0029632)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:35:24 UTC

Update Date

2024-04-30 19:39:48 UTC

Metabolite ID

MMDBc0029632

Metabolite Identification

Common Name

N-Acetyl-glucosamine 1-phosphate

Description

N-acetyl-glucosamine 1-phosphate is a member of the chemical class known as N-acetyl-alpha-hexosamine-1-phosphates. These are carbohydrates derivative which is structurally characterized by the presence of an hexosamine bearing a phosphate group attached to the C1 carbon atom, and another moeity N-linked through the amine group.

Structure

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

HMDB0001367
     RDKit          3D
N-Acetyl-glucosamine 1-phosphate
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.2533    0.0640    0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0160   -0.7044   -0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0343   -1.9567   -0.2576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7731   -0.0464   -0.1558 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000   -0.7267   -0.3059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3320   -0.3637    0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1893    0.9972    1.1155 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4894    1.3679    2.5988 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.4651    2.2304    3.4177 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016    2.2736    2.3839 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8605    0.0061    3.5165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6788   -0.6454    0.7331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    0.0723   -0.3608 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6793    0.0799   -0.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2243   -1.1766   -0.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755   -0.5814   -1.5885 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2326   -0.2346   -2.7506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -0.1780   -1.5945 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5764   -0.6455   -2.6753 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3680    0.4653    1.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1160   -0.5928   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2017    0.9292   -0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7096    1.0076   -0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6633   -1.8259   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -0.9840    1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7617    2.8000    1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5178    0.2383    4.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7786    1.1021   -0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9790    0.7211   -1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0167    0.6177    0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0558   -1.1128   -1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5889   -1.6978   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6674   -1.0442   -3.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0766    0.9373   -1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0634   -1.3928   -3.0736 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
  7  8  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 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  6
  6 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  1
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  1
 17 33  1  0
 18 34  1  1
 19 35  1  0
M  END


  Mrv0541 02231219052D          

 19 19  0  0  1  0            999 V2000
    0.0946   -0.6850    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0946    0.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6245   -1.0975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0596   -1.1127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6245    0.5525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8061    0.5525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3397   -0.6850    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6245   -1.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7712   -0.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3397    0.1400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8061    1.3776    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0437   -1.0975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4827   -1.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7673    0.1211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0437    0.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8061    2.1989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6311    1.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0151    1.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6719    0.0189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  1  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  6  0  0  0
  9 13  1  0  0  0  0
  9 14  2  0  0  0  0
 10 15  1  1  0  0  0
 11 16  1  0  0  0  0
 11 17  1  0  0  0  0
 11 18  2  0  0  0  0
 15 19  1  0  0  0  0
  7 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029632

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16NO9P/c1-3(11)9-5-7(13)6(12)4(2-10)17-8(5)18-19(14,15)16/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H2,14,15,16)/t4-,5-,6-,7-,8?/m1/s1

> <INCHI_KEY>
FZLJPEPAYPUMMR-RTRLPJTCSA-N

> <FORMULA>
C8H16NO9P

> <MOLECULAR_WEIGHT>
301.1877

> <EXACT_MASS>
301.056267627

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
25.406552682510437

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-2.00

> <JCHEM_LOGP>
-3.3441404429999997

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.238176832880029

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1819802553665197

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7889787416026043

> <JCHEM_POLAR_SURFACE_AREA>
165.78

> <JCHEM_REFRACTIVITY>
57.8976

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.84e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001367
     RDKit          3D
N-Acetyl-glucosamine 1-phosphate
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.2533    0.0640    0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0160   -0.7044   -0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0343   -1.9567   -0.2576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7731   -0.0464   -0.1558 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000   -0.7267   -0.3059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3320   -0.3637    0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1893    0.9972    1.1155 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4894    1.3679    2.5988 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.4651    2.2304    3.4177 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016    2.2736    2.3839 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8605    0.0061    3.5165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6788   -0.6454    0.7331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    0.0723   -0.3608 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6793    0.0799   -0.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2243   -1.1766   -0.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755   -0.5814   -1.5885 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2326   -0.2346   -2.7506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -0.1780   -1.5945 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5764   -0.6455   -2.6753 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3680    0.4653    1.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1160   -0.5928   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2017    0.9292   -0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7096    1.0076   -0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6633   -1.8259   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -0.9840    1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7617    2.8000    1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5178    0.2383    4.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7786    1.1021   -0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9790    0.7211   -1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0167    0.6177    0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0558   -1.1128   -1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5889   -1.6978   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6674   -1.0442   -3.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0766    0.9373   -1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0634   -1.3928   -3.0736 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
  7  8  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 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  6
  6 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  1
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  1
 17 33  1  0
 18 34  1  1
 19 35  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.177  -1.279   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.177   0.261   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.166  -2.049   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.978  -2.077   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0      -1.166   1.031   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.505   1.031   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.501  -1.279   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.166  -3.582   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.306  -1.307   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.501   0.261   0.000  0.00  0.00           C+0
HETATM   11  P   UNK     0       1.505   2.572   0.000  0.00  0.00           P+0
HETATM   12  O   UNK     0      -3.815  -2.049   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.634  -2.077   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.299   0.226   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.815   1.031   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.505   4.105   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.045   2.572   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.028   2.572   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.988   0.035   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12   10                                                  
CONECT    8    3                                                            
CONECT    9    4   13   14                                                  
CONECT   10    5   15    7                                                  
CONECT   11    6   16   17   18                                             
CONECT   12    7                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15   10   19                                                       
CONECT   16   11                                                            
CONECT   17   11                                                            
CONECT   18   11                                                            
CONECT   19   15                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0001367
HETATM    1  C1  UNL     1       4.253   0.064   0.019  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.016  -0.704  -0.137  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.034  -1.957  -0.258  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.773  -0.046  -0.156  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.500  -0.727  -0.306  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.332  -0.364   0.898  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.189   0.997   1.116  1.00  0.00           O  
HETATM    8  P1  UNL     1       0.489   1.368   2.599  1.00  0.00           P  
HETATM    9  O3  UNL     1      -0.465   2.230   3.418  1.00  0.00           O  
HETATM   10  O4  UNL     1       1.902   2.274   2.384  1.00  0.00           O  
HETATM   11  O5  UNL     1       0.861   0.006   3.516  1.00  0.00           O  
HETATM   12  O6  UNL     1      -1.679  -0.645   0.733  1.00  0.00           O  
HETATM   13  C5  UNL     1      -2.175   0.072  -0.361  1.00  0.00           C  
HETATM   14  C6  UNL     1      -3.679   0.080  -0.397  1.00  0.00           C  
HETATM   15  O7  UNL     1      -4.224  -1.177  -0.487  1.00  0.00           O  
HETATM   16  C7  UNL     1      -1.575  -0.581  -1.589  1.00  0.00           C  
HETATM   17  O8  UNL     1      -2.233  -0.235  -2.751  1.00  0.00           O  
HETATM   18  C8  UNL     1      -0.119  -0.178  -1.594  1.00  0.00           C  
HETATM   19  O9  UNL     1       0.576  -0.646  -2.675  1.00  0.00           O  
HETATM   20  H1  UNL     1       4.368   0.465   1.045  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.116  -0.593  -0.207  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.202   0.929  -0.691  1.00  0.00           H  
HETATM   23  H4  UNL     1       1.710   1.008  -0.058  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.663  -1.826  -0.402  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.028  -0.984   1.745  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.762   2.800   1.544  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.518   0.238   4.211  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.779   1.102  -0.255  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.979   0.721  -1.252  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.017   0.618   0.520  1.00  0.00           H  
HETATM   31  H12 UNL     1      -5.056  -1.113  -1.057  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.589  -1.698  -1.438  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.667  -1.044  -3.116  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.077   0.937  -1.490  1.00  0.00           H  
HETATM   35  H16 UNL     1       0.063  -1.393  -3.074  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   12   25
CONECT    7    8
CONECT    8    9    9   10   11
CONECT   10   26
CONECT   11   27
CONECT   12   13
CONECT   13   14   16   28
CONECT   14   15   29   30
CONECT   15   31
CONECT   16   17   18   32
CONECT   17   33
CONECT   18   19   34
CONECT   19   35
END

HMDB0001367
     RDKit          3D
N-Acetyl-glucosamine 1-phosphate
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.2533    0.0640    0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0160   -0.7044   -0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0343   -1.9567   -0.2576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7731   -0.0464   -0.1558 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000   -0.7267   -0.3059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3320   -0.3637    0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1893    0.9972    1.1155 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4894    1.3679    2.5988 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.4651    2.2304    3.4177 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016    2.2736    2.3839 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8605    0.0061    3.5165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6788   -0.6454    0.7331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755    0.0723   -0.3608 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6793    0.0799   -0.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2243   -1.1766   -0.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755   -0.5814   -1.5885 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2326   -0.2346   -2.7506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -0.1780   -1.5945 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5764   -0.6455   -2.6753 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3680    0.4653    1.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1160   -0.5928   -0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2017    0.9292   -0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7096    1.0076   -0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6633   -1.8259   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -0.9840    1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7617    2.8000    1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5178    0.2383    4.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7786    1.1021   -0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9790    0.7211   -1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0167    0.6177    0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0558   -1.1128   -1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5889   -1.6978   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6674   -1.0442   -3.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0766    0.9373   -1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0634   -1.3928   -3.0736 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
  7  8  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 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  6
  6 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  1
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  1
 17 33  1  0
 18 34  1  1
 19 35  1  0
M  END

Synonyms

Value	Source
2-(Acetylamino)-2-deoxy-D-glucopyranose 1-(dihydrogen phosphate)	ChEBI
2-Acetamido-2-deoxy-1-O-phosphono-D-glucopyranose	ChEBI
N-Acetyl-D-glucosamine 1-phosphate	ChEBI
N-Acetylglucosamine-1-phosphate	ChEBI
2-(Acetylamino)-2-deoxy-D-glucopyranose 1-(dihydrogen phosphoric acid)	Generator
N-Acetyl-D-glucosamine 1-phosphoric acid	Generator
N-Acetylglucosamine-1-phosphoric acid	Generator
N-Acetyl-glucosamine 1-phosphoric acid	Generator
D-Glucosamine 1-phosphate	HMDB
delta-Glucosamine 1-phosphate	HMDB
N-Acetyl-alpha-D-glucosamine 1-phosphate	HMDB
N-Acetyl-alpha-delta-glucosamine 1-phosphate	HMDB
N-Acetyl-delta-glucosamine 1-phosphate	HMDB
N-Acetyl-glucosamine-1-phosphate	HMDB
GlcNAc-1-phosphate	HMDB

Molecular Formula

C₈H₁₆NO₉P

Average Mass

301.1877

Monoisotopic Mass

301.056267627

IUPAC Name

{[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1OP(O)(O)=O

InChI Identifier

InChI=1S/C8H16NO9P/c1-3(11)9-5-7(13)6(12)4(2-10)17-8(5)18-19(14,15)16/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H2,14,15,16)/t4-,5-,6-,7-,8?/m1/s1

InChI Key

FZLJPEPAYPUMMR-RTRLPJTCSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acyl-alpha-hexosamines

Alternative Parents

Substituents

N-acyl-alpha-hexosamine
Hexose monosaccharide
Monosaccharide phosphate
Monoalkyl phosphate
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Primary alcohol
Carbonyl group
Organonitrogen compound
Organic oxide
Alcohol
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acetyl-D-glucosamine 1-phosphate (CHEBI:7125 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	18.4 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.3	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	-0.79	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	165.78 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.9 m³·mol⁻¹	ChemAxon
Polarizability	25.41 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	splash10-007k-9230000000-37cdd3ef185356d03c19	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0f6t-9211240000-817e06893a2ccced098b	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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1094000000-f1e04aaf05d431b8b0ab	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f7k-6290000000-6ff96a8c8bf54d5e8bfa	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6t-9620000000-3e2ee2ffc3801abdb7da	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002s-9211000000-7f3631860a58ca188060	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9110000000-9614f2b717f8fb17cc08	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-1a4f6aa02a49053d5b95	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0269000000-3075b429edd6182c13ba	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0559000000-4ca1cd5a6e65977c0024	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fk9-6900000000-1cb673f71135d27b87a1	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1019000000-7dfe9f6a1a82e9cc6643	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9021000000-405c928cec60fc405bdb	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004j-9000000000-5c37c1fa0342ac32c556	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces
Placenta
Saliva

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
MMDBp0192685	UDP-N-acetylhexosamine pyrophosphorylase	Enzyme	Q16222	Homo sapiens
MMDBp0193141	Phosphoacetylglucosamine mutase	Unknown	O95394	Homo sapiens
MMDBp0197002	UDP-N-acetylhexosamine pyrophosphorylase-like protein 1	Unknown	Q3KQV9

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000176	N-Acetyl-D-Glucosamine 6-Phosphate	N-Acetyl-glucosamine 1-phosphate	Not Available	VMH	11004509
MMDBr0007413	D-Glucosamine 1-phosphate	N-Acetyl-glucosamine 1-phosphate	Not Available	VMH	30371894
MMDBr0007588	N-Acetyl-glucosamine 1-phosphate	Uridine diphosphate-N-acetylglucosamine	Not Available	VMH	30371894

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	180	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	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	391	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	Metabolic reconstruction
Bacteria	Actinobacteria	128	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	123	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	1	Human feces	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	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Tenericutes	2	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Saliva	Detected and Quantified	0.135	0.363	uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.251	0.167	uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.282	0.623	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.326	0.327	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001367

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

N-ACETYL-D-GLUCOSAMINE-1-P

BiGG ID

43457

Wikipedia Link

Not Available

METLIN ID

6194

PubChem Compound

440272

PDB ID

Not Available

ChEBI ID

7125

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 N-Acetyl-glucosamine 1-phosphate (MMDBc0029632)

MOL for #<Metabolite:0x00007fdaf16d58c0>

3D MOL for #<Metabolite:0x00007fdaf16d58c0>

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3D-SDF for #<Metabolite:0x00007fdaf16d58c0>

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