MiMeDB: Showing metabocard for UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gamma-D-glutamyl-L-lysine (MMDBc0056360)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:23:42 UTC

Update Date

2022-08-12 20:09:42 UTC

MiMeDB ID

MMDBc0056360

Metabolite Identification

Common Name

UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gamma-D-glutamyl-L-lysine

Description

UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gamma-D-glutamyl-L-lysine belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Based on a literature review very few articles have been published on UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gamma-D-glutamyl-L-lysine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222232D          

 80 82  0  0  1  0            999 V2000
   11.7631   -0.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8256    1.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    0.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1131   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5256   -5.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5881   -3.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006   -4.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7688    6.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8756   -6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1014    6.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0631    3.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4256    4.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5881   -0.4717    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2381    0.9572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5381    0.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3506   -5.4730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0006   -2.6151    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.4756    3.1006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.2506    4.5296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5881   -4.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5225    6.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3006    1.6717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   16.7131    2.3862    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    8.0506   -6.9020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006    0.2427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131    0.9572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7631   -4.7586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5881   -1.9007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6087    5.5764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1876    5.4270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4756    4.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    1.6717    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.0006   -5.4730    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   25.1899    6.8818    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   21.4806    3.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    2.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1876    3.6321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8256   -1.1862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -0.4717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5881   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3506   -6.9020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -1.9007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -3.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0275    4.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    2.9901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   17.2362    3.5131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0131    3.8151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0631    0.9572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7355    5.1970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3006    3.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5381    2.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3631    3.8151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    3.8151    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    3.1006    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.1756   -1.1862    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4131    0.9572    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9381   -6.1875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4131   -3.3296    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6506    3.1006    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.8761    3.7945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8881    0.9572    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.3189    3.2788    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6506    1.6717    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.2552    4.4916    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8881    2.3862    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.3911    5.7569    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1256    1.6717    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  5  1  0  0  0  0
 11  9  2  0  0  0  0
 14  1  1  6  0  0  0
 15  2  1  1  0  0  0
 16  3  1  4  0  0  0
 17  6  1  0  0  0  0
 18  7  1  0  0  0  0
 19 12  1  1  0  0  0
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 21  8  1  0  0  0  0
 22  9  1  0  0  0  0
 24 20  1  0  0  0  0
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 35 10  1  0  0  0  0
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 36 29  2  0  0  0  0
 37 16  2  0  0  0  0
 23 37  1  6  0  0  0
 17 38  1  1  0  0  0
 38 21  2  0  0  0  0
 18 39  1  6  0  0  0
 39 28  2  0  0  0  0
 40 22  2  0  0  0  0
 40 34  1  0  0  0  0
 41 11  1  0  0  0  0
 30 41  1  1  0  0  0
 41 34  1  0  0  0  0
 42 12  1  0  0  0  0
 43 16  1  0  0  0  0
 21 44  1  4  0  0  0
 45 22  1  0  0  0  0
 24 46  1  6  0  0  0
 25 47  1  6  0  0  0
 26 48  1  6  0  0  0
 28 49  1  4  0  0  0
 29 50  1  4  0  0  0
 51 31  2  0  0  0  0
 52 31  1  0  0  0  0
 53 32  2  0  0  0  0
 54 32  1  0  0  0  0
 55 34  2  0  0  0  0
 60 13  1  0  0  0  0
 61 15  1  0  0  0  0
 27 61  1  6  0  0  0
 62 20  1  0  0  0  0
 62 30  1  0  0  0  0
 63 19  1  0  0  0  0
 63 33  1  0  0  0  0
 33 64  1  6  0  0  0
 66 56  1  0  0  0  0
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 67 65  1  0  0  0  0
 14 68  1  1  0  0  0
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 17 70  1  1  0  0  0
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 27 78  1  6  0  0  0
 30 79  1  6  0  0  0
 33 80  1  1  0  0  0
M  CHG  3  43  -1  44  -1  45  -1
M  END


  Mrv1652306172222232D          

 80 82  0  0  1  0            999 V2000
   11.7631   -0.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8256    1.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    0.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1131   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5256   -5.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5881   -3.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006   -4.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.0631    3.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4256    4.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5881   -0.4717    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2381    0.9572    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5381    0.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3506   -5.4730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0006   -2.6151    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.4756    3.1006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.2506    4.5296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5881   -4.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5225    6.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3006    1.6717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.7355    3.8621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   11.7631   -4.7586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   23.1876    5.4270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4756    4.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    1.6717    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.0006   -5.4730    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   25.1899    6.8818    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   21.4806    3.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    2.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1876    3.6321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8256   -1.1862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -0.4717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5881   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3506   -6.9020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -1.9007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.6651    2.6881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    3.5131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0131    3.8151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0631    0.9572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7355    5.1970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3006    3.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5381    2.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3631    3.8151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    3.8151    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    3.1006    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.1756   -1.1862    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4131    0.9572    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9381   -6.1875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4131   -3.3296    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6506    3.1006    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.8761    3.7945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8881    0.9572    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.3189    3.2788    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6506    1.6717    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.2552    4.4916    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8881    2.3862    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.3911    5.7569    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1256    1.6717    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  5  1  0  0  0  0
 11  9  2  0  0  0  0
 14  1  1  6  0  0  0
 15  2  1  1  0  0  0
 16  3  1  4  0  0  0
 17  6  1  0  0  0  0
 18  7  1  0  0  0  0
 19 12  1  1  0  0  0
 20 13  1  1  0  0  0
 21  8  1  0  0  0  0
 22  9  1  0  0  0  0
 24 20  1  0  0  0  0
 25 19  1  0  0  0  0
 26 24  1  0  0  0  0
 27 23  1  0  0  0  0
 27 25  1  0  0  0  0
 28 14  1  0  0  0  0
 29 15  1  0  0  0  0
 30 26  1  0  0  0  0
 31 17  1  0  0  0  0
 32 18  1  0  0  0  0
 33 23  1  0  0  0  0
 35 10  1  0  0  0  0
 36 14  1  0  0  0  0
 36 29  2  0  0  0  0
 37 16  2  0  0  0  0
 23 37  1  6  0  0  0
 17 38  1  1  0  0  0
 38 21  2  0  0  0  0
 18 39  1  6  0  0  0
 39 28  2  0  0  0  0
 40 22  2  0  0  0  0
 40 34  1  0  0  0  0
 41 11  1  0  0  0  0
 30 41  1  1  0  0  0
 41 34  1  0  0  0  0
 42 12  1  0  0  0  0
 43 16  1  0  0  0  0
 21 44  1  4  0  0  0
 45 22  1  0  0  0  0
 24 46  1  6  0  0  0
 25 47  1  6  0  0  0
 26 48  1  6  0  0  0
 28 49  1  4  0  0  0
 29 50  1  4  0  0  0
 51 31  2  0  0  0  0
 52 31  1  0  0  0  0
 53 32  2  0  0  0  0
 54 32  1  0  0  0  0
 55 34  2  0  0  0  0
 60 13  1  0  0  0  0
 61 15  1  0  0  0  0
 27 61  1  6  0  0  0
 62 20  1  0  0  0  0
 62 30  1  0  0  0  0
 63 19  1  0  0  0  0
 63 33  1  0  0  0  0
 33 64  1  6  0  0  0
 66 56  1  0  0  0  0
 66 57  2  0  0  0  0
 66 60  1  0  0  0  0
 66 65  1  0  0  0  0
 67 58  1  0  0  0  0
 67 59  2  0  0  0  0
 67 64  1  0  0  0  0
 67 65  1  0  0  0  0
 14 68  1  1  0  0  0
 15 69  1  6  0  0  0
 17 70  1  1  0  0  0
 18 71  1  6  0  0  0
 19 72  1  6  0  0  0
 20 73  1  6  0  0  0
 23 74  1  1  0  0  0
 24 75  1  1  0  0  0
 25 76  1  1  0  0  0
 26 77  1  1  0  0  0
 27 78  1  6  0  0  0
 30 79  1  6  0  0  0
 33 80  1  1  0  0  0
M  CHG  3  43  -1  44  -1  45  -1
M  END
> <DATABASE_ID>
MMDBc0056360

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)[O-])C(O)=N[C@@]([H])(C)C(O)=N[C@]([H])(CCC([O-])=N[C@@]([H])(CCCCN)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H55N7O24P2/c1-14(28(49)39-18(32(53)54)7-8-21(44)38-17(31(51)52)6-4-5-10-35)36-29(50)15(2)61-27-23(37-16(3)43)33(63-19(12-42)25(27)47)64-67(58,59)65-66(56,57)60-13-20-24(46)26(48)30(62-20)41-11-9-22(45)40-34(41)55/h9,11,14-15,17-20,23-27,30,33,42,46-48H,4-8,10,12-13,35H2,1-3H3,(H,36,50)(H,37,43)(H,38,44)(H,39,49)(H,51,52)(H,53,54)(H,56,57)(H,58,59)(H,40,45,55)/p-3/t14-,15+,17-,18+,19+,20+,23+,24+,25+,26+,27+,30+,33+/m0/s1

> <INCHI_KEY>
WXBLSQNZKMJACT-BYEZXYKXSA-K

> <FORMULA>
C34H52N7O24P2

> <MOLECULAR_WEIGHT>
1004.764

> <EXACT_MASS>
1004.255540318

> <JCHEM_ACCEPTOR_COUNT>
27

> <JCHEM_ATOM_COUNT>
119

> <JCHEM_AVERAGE_POLARIZABILITY>
90.07072387787038

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-N-[(1S)-5-amino-1-carboxypentyl]-4-carboxy-4-{[(2S)-2-{[(2R)-2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}butanecarboximidate

> <JCHEM_LOGP>
-4.319189124421353

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.6890802077930407

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7000769081849807

> <JCHEM_PKA_STRONGEST_BASIC>
10.20551268092046

> <JCHEM_POLAR_SURFACE_AREA>
503.27000000000015

> <JCHEM_REFRACTIVITY>
246.94100000000012

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-N-[(1S)-5-amino-1-carboxypentyl]-4-carboxy-4-{[(2S)-2-{[(2R)-2-{[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}butanecarboximidate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      21.958  -0.881   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.808   3.120   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.508   0.453   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.878 -11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.648 -10.216   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.498  -6.215   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.268  -7.549   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      44.368  12.567   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.568 -12.884   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      43.123  11.662   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.118   7.122   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      38.128   8.455   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.498  -0.881   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.578   1.787   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.738   1.787   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.188 -10.216   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.268  -4.882   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.888   5.788   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      39.668   8.455   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.498  -8.883   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      45.775  11.941   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      30.428   3.120   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      40.573   7.209   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      28.118   4.454   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      42.038   7.685   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      28.888   3.120   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      24.268  -2.214   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.808   0.453   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      42.038   9.225   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      21.958 -11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      25.808  -4.882   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      31.198   4.454   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      44.690   9.504   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      15.028 -12.884   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0      24.268   0.453   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0      31.198   1.787   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0      21.958  -8.883   0.000  0.00  0.00           N+0
HETATM   39  N   UNK     0      23.498  -3.548   0.000  0.00  0.00           N+0
HETATM   40  N   UNK     0      45.936  10.409   0.000  0.00  0.00           N+0
HETATM   41  N   UNK     0      43.284  10.130   0.000  0.00  0.00           N+0
HETATM   42  O   UNK     0      28.888   8.455   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      33.508   3.120   0.000  0.00  0.00           O-1
HETATM   44  O   UNK     0      24.268 -10.216   0.000  0.00  0.00           O-1
HETATM   45  O   UNK     0      47.021  12.846   0.000  0.00  0.00           O-1
HETATM   46  O   UNK     0      40.097   5.745   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      26.578   4.454   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      43.284   6.780   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      25.808  -2.214   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      26.578  -0.881   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      23.498 -11.550   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      21.188 -12.884   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      26.578  -3.548   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      26.578  -6.215   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      44.851   7.972   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      35.818   5.582   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      35.818   8.662   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      34.842   5.018   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      32.174   6.558   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      37.358   7.122   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      28.118   1.787   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      40.573   9.701   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      30.428   5.788   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      32.738   4.454   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      34.278   7.122   0.000  0.00  0.00           O+0
HETATM   66  P   UNK     0      35.818   7.122   0.000  0.00  0.00           P+0
HETATM   67  P   UNK     0      33.508   5.788   0.000  0.00  0.00           P+0
HETATM   68  H   UNK     0      22.728  -2.214   0.000  0.00  0.00           H+0
HETATM   69  H   UNK     0      25.038   1.787   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0      20.418 -11.550   0.000  0.00  0.00           H+0
HETATM   71  H   UNK     0      25.038  -6.215   0.000  0.00  0.00           H+0
HETATM   72  H   UNK     0      27.348   5.788   0.000  0.00  0.00           H+0
HETATM   73  H   UNK     0      38.969   7.083   0.000  0.00  0.00           H+0
HETATM   74  H   UNK     0      29.658   1.787   0.000  0.00  0.00           H+0
HETATM   75  H   UNK     0      41.662   6.120   0.000  0.00  0.00           H+0
HETATM   76  H   UNK     0      27.348   3.120   0.000  0.00  0.00           H+0
HETATM   77  H   UNK     0      43.410   8.384   0.000  0.00  0.00           H+0
HETATM   78  H   UNK     0      29.658   4.454   0.000  0.00  0.00           H+0
HETATM   79  H   UNK     0      41.797  10.746   0.000  0.00  0.00           H+0
HETATM   80  H   UNK     0      31.968   3.120   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4    5    6                                                       
CONECT    5    4   10                                                       
CONECT    6    4   17                                                       
CONECT    7    8   18                                                       
CONECT    8    7   21                                                       
CONECT    9   11   22                                                       
CONECT   10    5   35                                                       
CONECT   11    9   41                                                       
CONECT   12   19   42                                                       
CONECT   13   20   60                                                       
CONECT   14    1   28   36   68                                             
CONECT   15    2   29   61   69                                             
CONECT   16    3   37   43                                                  
CONECT   17    6   31   38   70                                             
CONECT   18    7   32   39   71                                             
CONECT   19   12   25   63   72                                             
CONECT   20   13   24   62   73                                             
CONECT   21    8   38   44                                                  
CONECT   22    9   40   45                                                  
CONECT   23   27   33   37   74                                             
CONECT   24   20   26   46   75                                             
CONECT   25   19   27   47   76                                             
CONECT   26   24   30   48   77                                             
CONECT   27   23   25   61   78                                             
CONECT   28   14   39   49                                                  
CONECT   29   15   36   50                                                  
CONECT   30   26   41   62   79                                             
CONECT   31   17   51   52                                                  
CONECT   32   18   53   54                                                  
CONECT   33   23   63   64   80                                             
CONECT   34   40   41   55                                                  
CONECT   35   10                                                            
CONECT   36   14   29                                                       
CONECT   37   16   23                                                       
CONECT   38   17   21                                                       
CONECT   39   18   28                                                       
CONECT   40   22   34                                                       
CONECT   41   11   30   34                                                  
CONECT   42   12                                                            
CONECT   43   16                                                            
CONECT   44   21                                                            
CONECT   45   22                                                            
CONECT   46   24                                                            
CONECT   47   25                                                            
CONECT   48   26                                                            
CONECT   49   28                                                            
CONECT   50   29                                                            
CONECT   51   31                                                            
CONECT   52   31                                                            
CONECT   53   32                                                            
CONECT   54   32                                                            
CONECT   55   34                                                            
CONECT   56   66                                                            
CONECT   57   66                                                            
CONECT   58   67                                                            
CONECT   59   67                                                            
CONECT   60   13   66                                                       
CONECT   61   15   27                                                       
CONECT   62   20   30                                                       
CONECT   63   19   33                                                       
CONECT   64   33   67                                                       
CONECT   65   66   67                                                       
CONECT   66   56   57   60   65                                             
CONECT   67   58   59   64   65                                             
CONECT   68   14                                                            
CONECT   69   15                                                            
CONECT   70   17                                                            
CONECT   71   18                                                            
CONECT   72   19                                                            
CONECT   73   20                                                            
CONECT   74   23                                                            
CONECT   75   24                                                            
CONECT   76   25                                                            
CONECT   77   26                                                            
CONECT   78   27                                                            
CONECT   79   30                                                            
CONECT   80   33                                                            
MASTER        0    0    0    0    0    0    0    0   80    0  164    0
END

Synonyms

Value	Source
UDP-N-Acetyl-a-D-muramoyl-L-alanyl-g-D-glutamyl-L-lysine	Generator
UDP-N-Acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-L-lysine	Generator

Chemical Formula

C₃₄H₅₂N₇O₂₄P₂

Average Molecular Weight

1004.764

Monoisotopic Molecular Weight

1004.255540318

IUPAC Name

(4R)-N-[(1S)-5-amino-1-carboxypentyl]-4-carboxy-4-{[(2S)-2-{[(2R)-2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}butanecarboximidate

Traditional Name

(4R)-N-[(1S)-5-amino-1-carboxypentyl]-4-carboxy-4-{[(2S)-2-{[(2R)-2-{[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}butanecarboximidate

CAS Registry Number

Not Available

SMILES

[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)[O-])C(O)=N[C@@]([H])(C)C(O)=N[C@]([H])(CCC([O-])=N[C@@]([H])(CCCCN)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C34H55N7O24P2/c1-14(28(49)39-18(32(53)54)7-8-21(44)38-17(31(51)52)6-4-5-10-35)36-29(50)15(2)61-27-23(37-16(3)43)33(63-19(12-42)25(27)47)64-67(58,59)65-66(56,57)60-13-20-24(46)26(48)30(62-20)41-11-9-22(45)40-34(41)55/h9,11,14-15,17-20,23-27,30,33,42,46-48H,4-8,10,12-13,35H2,1-3H3,(H,36,50)(H,37,43)(H,38,44)(H,39,49)(H,51,52)(H,53,54)(H,56,57)(H,58,59)(H,40,45,55)/p-3/t14-,15+,17-,18+,19+,20+,23+,24+,25+,26+,27+,30+,33+/m0/s1

InChI Key

WXBLSQNZKMJACT-BYEZXYKXSA-K

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Alpha-dipeptide
Gamma-glutamyl alpha-amino acid
Alpha peptide
Saccharolipid
Pentose phosphate
Pentose-5-phosphate
Glutamine or derivatives
N-acyl-alpha-hexosamine
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Glycosyl compound
N-glycosyl compound
Alanine or derivatives
Organic pyrophosphate
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Monosaccharide phosphate
Medium-chain fatty acid
Hydroxy fatty acid
Pyrimidone
Hydropyrimidine
Fatty amide
Oxane
Dicarboxylic acid or derivatives
Monosaccharide
N-acyl-amine
Alkyl phosphate
Pyrimidine
Fatty acid
Fatty acyl
Organic phosphoric acid derivative
Phosphoric acid ester
Acetamide
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Amino acid
Carboxylic acid salt
Carboxamide group
Amino acid or derivatives
Lactam
Secondary alcohol
Secondary carboxylic acid amide
Urea
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Organooxygen compound
Hydrocarbon derivative
Amine
Primary alcohol
Organic salt
Primary amine
Carbonyl group
Organic oxygen compound
Alcohol
Organic nitrogen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-L-lysine(3-) (CHEBI:83903 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-4.3	ChemAxon
pKa (Strongest Acidic)	1.7	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	27	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	503.27 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	246.94 m³·mol⁻¹	ChemAxon
Polarizability	90.07 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Firmicutes	37	Human ; Cattle ; Human Feces
	Thermotogae	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34448899

KEGG Compound ID

Not Available

BioCyc ID

CPD-209

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86290123

PDB ID

Not Available

ChEBI ID

83903

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gamma-D-glutamyl-L-lysine (MMDBc0056360)

MOL for #<Metabolite:0x000055b76e0b3558>

3D MOL for #<Metabolite:0x000055b76e0b3558>

3D SDF for #<Metabolite:0x000055b76e0b3558>

3D-SDF for #<Metabolite:0x000055b76e0b3558>

PDB for #<Metabolite:0x000055b76e0b3558>

3D PDB for #<Metabolite:0x000055b76e0b3558>

SMILES for #<Metabolite:0x000055b76e0b3558>

INCHI for #<Metabolite:0x000055b76e0b3558>

Structure for #<Metabolite:0x000055b76e0b3558>

3D Structure for #<Metabolite:0x000055b76e0b3558>