NP-MRD: Showing NP-Card for N-Acetyl-D-glucosamine 1-phosphate (NP0002636)

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Record Information

Version

1.0

Created at

2020-11-23 18:25:46 UTC

Updated at

2021-08-12 19:51:43 UTC

NP-MRD ID

NP0002636

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetyl-D-glucosamine 1-phosphate

Provided By

BMRB

Description

N-acetyl-alpha-D-glucosamine 1-phosphate is also known as alpha-glcnac-(1->o)PO3H2 or 1-(N-acetyl-a-D-glucosamine) phosphoric acid. N-Acetyl-D-glucosamine 1-phosphate is found in Escherichia coli K1. It was first documented in 2003 (PMID: 12626405). Based on a literature review very few articles have been published on N-acetyl-alpha-D-glucosamine 1-phosphate (PMID: 17984079) (PMID: 18048019).

Structure

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


     RDKit          2D

 35 35  0  0  0  0  0  0  0  0999 V2000
   -4.9724    0.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030   -0.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603   -1.9607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3762    0.2380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1068   -0.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5402    0.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4829    2.3266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    3.0264    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.8439    1.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1441    4.3532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1706    3.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9458    1.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8654   -0.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1348   -0.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -1.7518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2988   -1.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2415   -3.0413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1872   -1.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5140   -2.4460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7715   -0.9321    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1733    1.6067    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2418    1.1364    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4587    1.2186    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1142   -1.6725    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4697    1.1513    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9432    5.6226    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4400    2.9271    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728    0.9578    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7955   -1.6740    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9339    0.3167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7310   -1.0520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0517   -1.8045    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5109   -3.8405    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2715   -3.1744    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5714   -3.9449    0.0000 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
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 18  5  1  0
  1 20  1  1
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  1 22  1  0
  4 23  1  0
  5 24  1  6
  6 25  1  6
 10 26  1  0
 11 27  1  0
 13 28  1  1
 14 29  1  6
 14 30  1  0
 15 31  1  0
 16 32  1  6
 17 33  1  0
 18 34  1  1
 19 35  1  0
M  END

NP0002636
     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
    3.5072   -2.3945    1.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694   -2.2032    1.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2307   -3.0520    1.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6798   -1.0500    0.4827 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3068   -0.8449    0.1814 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2565    0.4456    0.7289 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1729    1.4776   -0.0674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9386    2.7153    0.7376 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4542    3.7014   -0.2980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1799    3.5548    1.7012 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2252    2.2297    1.6817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6580    0.3541    0.5538 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6549   -1.8762   -1.9668 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7829   -3.4620    1.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3911   -0.3647    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3373   -1.6683    0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0440    0.5618    1.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9160    2.9167    1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5738    0.8465   -2.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0404   -0.0875   -0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4691    1.9272    0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4445    0.1782   -1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1378   -2.2022   -2.7447 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
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 18 19  1  0
 18  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  1
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 11 27  1  0
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 16 32  1  1
 17 33  1  0
 18 34  1  6
 19 35  1  0
M  END


     RDKit          2D

 35 35  0  0  0  0  0  0  0  0999 V2000
   -4.9724    0.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030   -0.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603   -1.9607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3762    0.2380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1068   -0.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5402    0.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4829    2.3266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    3.0264    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.8439    1.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1441    4.3532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1706    3.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9458    1.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8654   -0.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1348   -0.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -1.7518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2988   -1.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2415   -3.0413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1872   -1.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5140   -2.4460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4400    2.9271    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7955   -1.6740    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5109   -3.8405    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2715   -3.1744    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5714   -3.9449    0.0000 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
  8  7  1  1
  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  1
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  6
  6 25  1  6
 10 26  1  0
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 13 28  1  1
 14 29  1  6
 14 30  1  0
 15 31  1  0
 16 32  1  6
 17 33  1  0
 18 34  1  1
 19 35  1  0
M  END
> <DATABASE_ID>
NP0002636

> <DATABASE_NAME>
NP-MRD

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

> <FORMULA>
C8H16NO9P

> <MOLECULAR_WEIGHT>
301.1877

> <EXACT_MASS>
301.056267627

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.3125788547967

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-3.3441404429999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.238176777203131

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1769426926362891

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5739791759132924

> <JCHEM_POLAR_SURFACE_AREA>
165.78

> <JCHEM_REFRACTIVITY>
57.8976

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
D-glucosamine 1-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002636
     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
    3.5072   -2.3945    1.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694   -2.2032    1.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2307   -3.0520    1.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6798   -1.0500    0.4827 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3068   -0.8449    0.1814 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2565    0.4456    0.7289 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1729    1.4776   -0.0674 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1799    3.5548    1.7012 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6580    0.3541    0.5538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522    0.4258   -0.8019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4040    0.7023   -1.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6945    1.9349   -0.4265 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8484   -0.9266   -2.7921 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0624   -0.8009   -1.3333 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6549   -1.8762   -1.9668 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0974   -1.9258    0.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7829   -3.4620    1.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3911   -0.3647    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3373   -1.6683    0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0440    0.5618    1.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0104    3.3366    2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9160    2.9167    1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3795    1.2867   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5738    0.8465   -2.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0404   -0.0875   -0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4691    1.9272    0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8026   -1.7085   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7431   -1.3434   -2.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4445    0.1782   -1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1378   -2.2022   -2.7447 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  1
  6 25  1  1
 10 26  1  0
 11 27  1  0
 13 28  1  6
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  1
 17 33  1  0
 18 34  1  6
 19 35  1  0
M  END

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.667  -1.540   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   18  P   UNK     0       2.667   3.080   0.000  0.00  0.00           P+0
HETATM   19  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   15    2    3                                                  
CONECT    2    1    6                                                       
CONECT    3    1    7    4                                                  
CONECT    4    3    8    5                                                  
CONECT    5    4   10    6                                                  
CONECT    6    5    2   11                                                  
CONECT    7    3    9                                                       
CONECT    8    4                                                            
CONECT    9    7   13   14                                                  
CONECT   10    5                                                            
CONECT   11    6   12                                                       
CONECT   12   11                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15    1   18                                                       
CONECT   16   18                                                            
CONECT   17   18                                                            
CONECT   18   15   16   17   19                                             
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    NP0002636
HETATM    1  C1  UNL     1       3.507  -2.395   1.494  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.069  -2.203   1.191  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.231  -3.052   1.562  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.680  -1.050   0.483  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.307  -0.845   0.181  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.257   0.446   0.729  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.173   1.478  -0.067  1.00  0.00           O  
HETATM    8  P1  UNL     1       0.939   2.715   0.738  1.00  0.00           P  
HETATM    9  O3  UNL     1       1.454   3.701  -0.298  1.00  0.00           O  
HETATM   10  O4  UNL     1      -0.180   3.555   1.701  1.00  0.00           O  
HETATM   11  O5  UNL     1       2.225   2.230   1.682  1.00  0.00           O  
HETATM   12  O6  UNL     1      -1.658   0.354   0.554  1.00  0.00           O  
HETATM   13  C5  UNL     1      -1.952   0.426  -0.802  1.00  0.00           C  
HETATM   14  C6  UNL     1      -3.404   0.702  -1.039  1.00  0.00           C  
HETATM   15  O7  UNL     1      -3.694   1.935  -0.426  1.00  0.00           O  
HETATM   16  C7  UNL     1      -1.451  -0.816  -1.469  1.00  0.00           C  
HETATM   17  O8  UNL     1      -1.848  -0.927  -2.792  1.00  0.00           O  
HETATM   18  C8  UNL     1       0.062  -0.801  -1.333  1.00  0.00           C  
HETATM   19  O9  UNL     1       0.655  -1.876  -1.967  1.00  0.00           O  
HETATM   20  H1  UNL     1       3.773  -1.868   2.425  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.097  -1.926   0.669  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.783  -3.462   1.583  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.391  -0.365   0.188  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.337  -1.668   0.564  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.044   0.562   1.790  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.010   3.337   2.657  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.916   2.917   1.669  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.379   1.287  -1.251  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.574   0.846  -2.126  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.040  -0.087  -0.631  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.469   1.927   0.538  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.803  -1.708  -0.890  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.743  -1.343  -2.873  1.00  0.00           H  
HETATM   34  H15 UNL     1       0.444   0.178  -1.688  1.00  0.00           H  
HETATM   35  H16 UNL     1       0.138  -2.202  -2.745  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

NP0002636
     RDKit          3D

35 35  0  0  0  0  0  0  0  0999 V2000
    3.5072   -2.3945    1.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694   -2.2032    1.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2307   -3.0520    1.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6798   -1.0500    0.4827 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3068   -0.8449    0.1814 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2565    0.4456    0.7289 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1729    1.4776   -0.0674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9386    2.7153    0.7376 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4542    3.7014   -0.2980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1799    3.5548    1.7012 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2252    2.2297    1.6817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6580    0.3541    0.5538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522    0.4258   -0.8019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4040    0.7023   -1.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6945    1.9349   -0.4265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4507   -0.8159   -1.4694 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8484   -0.9266   -2.7921 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0624   -0.8009   -1.3333 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6549   -1.8762   -1.9668 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7728   -1.8684    2.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -1.9258    0.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7829   -3.4620    1.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3911   -0.3647    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3373   -1.6683    0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0440    0.5618    1.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0104    3.3366    2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9160    2.9167    1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3795    1.2867   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5738    0.8465   -2.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0404   -0.0875   -0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4691    1.9272    0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8026   -1.7085   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7431   -1.3434   -2.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4445    0.1782   -1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1378   -2.2022   -2.7447 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  1
  6 25  1  1
 10 26  1  0
 11 27  1  0
 13 28  1  6
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  1
 17 33  1  0
 18 34  1  6
 19 35  1  0
M  END

View in JSmol

Synonyms

Value	Source
1-(N-Acetyl-alpha-D-glucosamine) phosphate	ChEBI
2-(ACETYLAMINO)-2-deoxy-1-O-phosphono-ALPHA-D-glucopyranose	ChEBI
2-Acetamido-2-deoxy-1-O-phosphono-alpha-D-glucopyranose	ChEBI
2-N-Acetylglucosamine 1-phosphate	ChEBI
alpha-GlcNAc-(1->o)PO3H2	ChEBI
alpha-GlcNAc-1-p	ChEBI
GlcNAc1alpha-phosphate	ChEBI
N-Acetyl-alpha-D-glucosamine 1-(dihydrogen phosphate)	ChEBI
N-Acetylglucosamine-1-phosphate	ChEBI
1-(N-Acetyl-a-D-glucosamine) phosphate	Generator
1-(N-Acetyl-a-D-glucosamine) phosphoric acid	Generator
1-(N-Acetyl-alpha-D-glucosamine) phosphoric acid	Generator
1-(N-Acetyl-α-D-glucosamine) phosphate	Generator
1-(N-Acetyl-α-D-glucosamine) phosphoric acid	Generator
2-(ACETYLAMINO)-2-deoxy-1-O-phosphono-a-D-glucopyranose	Generator
2-(ACETYLAMINO)-2-deoxy-1-O-phosphono-α-D-glucopyranose	Generator
2-Acetamido-2-deoxy-1-O-phosphono-a-D-glucopyranose	Generator
2-Acetamido-2-deoxy-1-O-phosphono-α-D-glucopyranose	Generator
2-N-Acetylglucosamine 1-phosphoric acid	Generator
a-GlcNAc-(1->o)PO3H2	Generator
Α-glcnac-(1->o)PO3H2	Generator
a-GlcNAc-1-p	Generator
Α-glcnac-1-p	Generator
GlcNAc1a-phosphate	Generator
GlcNAc1a-phosphoric acid	Generator
GlcNAc1alpha-phosphoric acid	Generator
GlcNAc1α-phosphate	Generator
GlcNAc1α-phosphoric acid	Generator
N-Acetyl-a-D-glucosamine 1-(dihydrogen phosphate)	Generator
N-Acetyl-a-D-glucosamine 1-(dihydrogen phosphoric acid)	Generator
N-Acetyl-alpha-D-glucosamine 1-(dihydrogen phosphoric acid)	Generator
N-Acetyl-α-D-glucosamine 1-(dihydrogen phosphate)	Generator
N-Acetyl-α-D-glucosamine 1-(dihydrogen phosphoric acid)	Generator
N-Acetylglucosamine-1-phosphoric acid	Generator
N-Acetyl-a-D-glucosamine 1-phosphate	Generator
N-Acetyl-a-D-glucosamine 1-phosphoric acid	Generator
N-Acetyl-alpha-D-glucosamine 1-phosphoric acid	Generator
N-Acetyl-α-D-glucosamine 1-phosphate	Generator
N-Acetyl-α-D-glucosamine 1-phosphoric acid	Generator
GlcNAc-1-phosphate	MeSH

Chemical Formula

C₈H₁₆NO₉P

Average Mass

301.1877 Da

Monoisotopic Mass

301.05627 Da

IUPAC Name

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

Traditional Name

D-glucosamine 1-phosphate

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(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-FMDGEEDCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, 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
Escherichia coli K1	Bacteria	KNApSAcK

Chemical Taxonomy

Description

This compound 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

2-acetamido-2-deoxy-D-glucopyranose 1-phosphate (CHEBI:16446 )

Physical Properties

State

Not Available

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
logP	-3.3	ChemAxon
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	-1.6	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	25.31 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB031023

KNApSAcK ID

Not Available

Chemspider ID

389323

KEGG Compound ID

C04501

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

16446

Good Scents ID

Not Available

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Wuhrer M, Grimm C, Zahringer U, Dennis RD, Berkefeld CM, Idris MA, Geyer R: A novel GlcNAcalpha1-HPO3-6Gal(1-1)ceramide antigen and alkylated inositol-phosphoglycerolipids expressed by the liver fluke Fasciola hepatica. Glycobiology. 2003 Feb;13(2):129-37. doi: 10.1093/glycob/cwg005. Epub 2002 Oct 30. [PubMed:12626405 ]
Khaled A, Piotrowska O, Dominiak K, Auge C: Exploring specificity of glycosyltransferases: synthesis of new sugar nucleotide related molecules as putative donor substrates. Carbohydr Res. 2008 Feb 4;343(2):167-78. doi: 10.1016/j.carres.2007.11.009. Epub 2007 Nov 17. [PubMed:18048019 ]

Showing NP-Card for N-Acetyl-D-glucosamine 1-phosphate (NP0002636)

MOL for NP0002636 (N-Acetyl-D-glucosamine 1-phosphate)

3D MOL for NP0002636 (N-Acetyl-D-glucosamine 1-phosphate)

3D SDF for NP0002636 (N-Acetyl-D-glucosamine 1-phosphate)

3D-SDF for NP0002636 (N-Acetyl-D-glucosamine 1-phosphate)

PDB for NP0002636 (N-Acetyl-D-glucosamine 1-phosphate)

3D PDB for NP0002636 (N-Acetyl-D-glucosamine 1-phosphate)

SMILES for NP0002636 (N-Acetyl-D-glucosamine 1-phosphate)

INCHI for NP0002636 (N-Acetyl-D-glucosamine 1-phosphate)

Structure for NP0002636 (N-Acetyl-D-glucosamine 1-phosphate)

3D Structure for NP0002636 (N-Acetyl-D-glucosamine 1-phosphate)