MiMeDB: Showing metabocard for UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-D-glutamic acid (MMDBc0056359)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:23:41 UTC

Update Date

2022-08-12 20:09:42 UTC

Metabolite ID

MMDBc0056359

Metabolite Identification

Common Name

UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-D-glutamic acid

Description

UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-D-glutamate, also known as UDP-N-acetyl-a-D-muramoyl-L-alanyl-D-glutamic acid, 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-D-glutamate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222232D          

 70 72  0  0  1  0            999 V2000
   11.1592   -0.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8717   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0967   -2.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6842   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4010   -6.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6473   -6.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8217   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717   -0.7441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.6342   -1.4586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2842   -4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9217   -2.1730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1092   -1.4586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.2342   -5.7454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.4872   -7.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.8986   -6.4991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2842   -1.4586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.5117   -7.0511    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8717   -2.1730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1592   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2262   -6.6386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3342   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1092   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.0661   -7.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3967   -0.7441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8717   -3.6020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3342   -1.4586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8198   -8.1302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9799   -6.9741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3467   -0.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1092   -4.3164    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   24.2409   -7.9808    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.4467   -3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4467   -2.1730    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   19.0917   -6.6706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8717   -0.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4255   -7.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717   -2.1730    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   12.3967   -2.1730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9217   -3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3987   -8.2796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2987   -3.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8697   -4.7289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3467   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3467   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9967   -5.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467   -2.1730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0547   -5.8316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217   -2.1730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217   -3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1717   -3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5842   -4.3164    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.3467   -3.6020    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.7467   -0.7441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2217   -0.7441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5092   -2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6967   -0.7441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.4103   -5.7886    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4592   -2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.6851   -7.2959    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4592   -1.4586    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.2036   -7.5004    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6967   -2.1730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.8673   -6.1194    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6967   -3.6020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
 10  1  1  6  0  0  0
 11  2  1  1  0  0  0
 12  3  1  4  0  0  0
 13  4  1  0  0  0  0
 14  8  1  1  0  0  0
 15  9  1  1  0  0  0
 16  6  1  0  0  0  0
 17  5  1  0  0  0  0
 19 15  1  0  0  0  0
 20 14  1  0  0  0  0
 21 19  1  0  0  0  0
 22 18  1  0  0  0  0
 22 20  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  1  0  0  0  0
 25 21  1  0  0  0  0
 26 13  1  0  0  0  0
 27 18  1  0  0  0  0
 29 10  1  0  0  0  0
 29 24  2  0  0  0  0
 30 12  2  0  0  0  0
 18 30  1  6  0  0  0
 13 31  1  6  0  0  0
 31 23  2  0  0  0  0
 32 16  2  0  0  0  0
 32 28  1  0  0  0  0
 33  7  1  0  0  0  0
 25 33  1  1  0  0  0
 33 28  1  0  0  0  0
 34  8  1  0  0  0  0
 35 12  1  0  0  0  0
 36 16  1  0  0  0  0
 37 17  2  0  0  0  0
 38 17  1  0  0  0  0
 19 39  1  6  0  0  0
 20 40  1  6  0  0  0
 21 41  1  6  0  0  0
 23 42  1  4  0  0  0
 24 43  1  4  0  0  0
 44 26  2  0  0  0  0
 45 26  1  0  0  0  0
 46 28  2  0  0  0  0
 51  9  1  0  0  0  0
 52 11  1  0  0  0  0
 22 52  1  6  0  0  0
 53 15  1  0  0  0  0
 53 25  1  0  0  0  0
 54 14  1  0  0  0  0
 54 27  1  0  0  0  0
 27 55  1  6  0  0  0
 57 47  1  0  0  0  0
 57 48  2  0  0  0  0
 57 51  1  0  0  0  0
 57 56  1  0  0  0  0
 58 49  1  0  0  0  0
 58 50  2  0  0  0  0
 58 55  1  0  0  0  0
 58 56  1  0  0  0  0
 10 59  1  1  0  0  0
 11 60  1  6  0  0  0
 13 61  1  6  0  0  0
 14 62  1  6  0  0  0
 15 63  1  6  0  0  0
 18 64  1  1  0  0  0
 19 65  1  1  0  0  0
 20 66  1  1  0  0  0
 21 67  1  1  0  0  0
 22 68  1  6  0  0  0
 25 69  1  6  0  0  0
 27 70  1  1  0  0  0
M  CHG  4  35  -1  36  -1  38  -1  42  -1
M  END


  Mrv1652306172222232D          

 70 72  0  0  1  0            999 V2000
   11.1592   -0.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8717   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0967   -2.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6842   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4010   -6.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6473   -6.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8217   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717   -0.7441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.6342   -1.4586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2842   -4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9217   -2.1730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1092   -1.4586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.2342   -5.7454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.4872   -7.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.8986   -6.4991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2842   -1.4586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.5117   -7.0511    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8717   -2.1730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1592   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2262   -6.6386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3342   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1092   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.0661   -7.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3967   -0.7441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8717   -3.6020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3342   -1.4586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8198   -8.1302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9799   -6.9741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3467   -0.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1092   -4.3164    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   24.2409   -7.9808    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.4467   -3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4467   -2.1730    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   19.0917   -6.6706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8717   -0.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4255   -7.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717   -2.1730    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   12.3967   -2.1730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9217   -3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3987   -8.2796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2987   -3.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8697   -4.7289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3467   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3467   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9967   -5.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467   -2.1730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0547   -5.8316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217   -2.1730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217   -3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1717   -3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5842   -4.3164    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.3467   -3.6020    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.7467   -0.7441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2217   -0.7441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5092   -2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6967   -0.7441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.4103   -5.7886    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4592   -2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.6851   -7.2959    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4592   -1.4586    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.2036   -7.5004    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6967   -2.1730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.8673   -6.1194    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6967   -3.6020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
 10  1  1  6  0  0  0
 11  2  1  1  0  0  0
 12  3  1  4  0  0  0
 13  4  1  0  0  0  0
 14  8  1  1  0  0  0
 15  9  1  1  0  0  0
 16  6  1  0  0  0  0
 17  5  1  0  0  0  0
 19 15  1  0  0  0  0
 20 14  1  0  0  0  0
 21 19  1  0  0  0  0
 22 18  1  0  0  0  0
 22 20  1  0  0  0  0
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 24 11  1  0  0  0  0
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 26 13  1  0  0  0  0
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 29 10  1  0  0  0  0
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 18 30  1  6  0  0  0
 13 31  1  6  0  0  0
 31 23  2  0  0  0  0
 32 16  2  0  0  0  0
 32 28  1  0  0  0  0
 33  7  1  0  0  0  0
 25 33  1  1  0  0  0
 33 28  1  0  0  0  0
 34  8  1  0  0  0  0
 35 12  1  0  0  0  0
 36 16  1  0  0  0  0
 37 17  2  0  0  0  0
 38 17  1  0  0  0  0
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 21 41  1  6  0  0  0
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 24 43  1  4  0  0  0
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 45 26  1  0  0  0  0
 46 28  2  0  0  0  0
 51  9  1  0  0  0  0
 52 11  1  0  0  0  0
 22 52  1  6  0  0  0
 53 15  1  0  0  0  0
 53 25  1  0  0  0  0
 54 14  1  0  0  0  0
 54 27  1  0  0  0  0
 27 55  1  6  0  0  0
 57 47  1  0  0  0  0
 57 48  2  0  0  0  0
 57 51  1  0  0  0  0
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 58 49  1  0  0  0  0
 58 50  2  0  0  0  0
 58 55  1  0  0  0  0
 58 56  1  0  0  0  0
 10 59  1  1  0  0  0
 11 60  1  6  0  0  0
 13 61  1  6  0  0  0
 14 62  1  6  0  0  0
 15 63  1  6  0  0  0
 18 64  1  1  0  0  0
 19 65  1  1  0  0  0
 20 66  1  1  0  0  0
 21 67  1  1  0  0  0
 22 68  1  6  0  0  0
 25 69  1  6  0  0  0
 27 70  1  1  0  0  0
M  CHG  4  35  -1  36  -1  38  -1  42  -1
M  END
> <DATABASE_ID>
MMDBc0056359

> <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-])=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H43N5O23P2/c1-10(23(42)31-13(26(44)45)4-5-17(37)38)29-24(43)11(2)52-22-18(30-12(3)35)27(54-14(8-34)20(22)40)55-58(49,50)56-57(47,48)51-9-15-19(39)21(41)25(53-15)33-7-6-16(36)32-28(33)46/h6-7,10-11,13-15,18-22,25,27,34,39-41H,4-5,8-9H2,1-3H3,(H,29,43)(H,30,35)(H,31,42)(H,37,38)(H,44,45)(H,47,48)(H,49,50)(H,32,36,46)/p-4/t10-,11+,13+,14+,15+,18+,19+,20+,21+,22+,25+,27+/m0/s1

> <INCHI_KEY>
OJZCATPXPWFLHF-HPUCEMLMSA-J

> <FORMULA>
C28H39N5O23P2

> <MOLECULAR_WEIGHT>
875.582

> <EXACT_MASS>
875.153300851

> <JCHEM_ACCEPTOR_COUNT>
24

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
75.09617100049677

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-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-oxidopropylidene]amino}butanoate

> <JCHEM_LOGP>
-3.194644732333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
2.79286785854558

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7109296604504385

> <JCHEM_POLAR_SURFACE_AREA>
447.4900000000001

> <JCHEM_REFRACTIVITY>
222.6468000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-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-oxidopropylidene]amino}butanoate

> <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      20.830  -0.055   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.220  -1.389   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.760  -9.391   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.980  -4.056   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.210  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      43.682 -12.740   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      42.275 -12.113   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.840  -1.389   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      37.000  -9.391   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.600  -1.389   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.450  -2.723   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.530  -8.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.520  -4.056   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.070  -2.723   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.770 -10.725   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      43.843 -14.271   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.530  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.144 -12.132   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.530  -2.723   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      38.289 -13.162   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.760  -4.056   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.830  -2.723   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.910  -2.723   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      39.622 -12.392   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.290  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.070  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      41.190 -14.550   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      23.140  -1.389   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0      27.760  -6.724   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0      19.290  -2.723   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0      42.597 -15.176   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0      41.029 -13.018   0.000  0.00  0.00           N+0
HETATM   34  O   UNK     0      32.380  -1.389   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      30.070  -8.057   0.000  0.00  0.00           O-1
HETATM   36  O   UNK     0      45.250 -14.898   0.000  0.00  0.00           O-1
HETATM   37  O   UNK     0      13.900  -6.724   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      13.900  -4.056   0.000  0.00  0.00           O-1
HETATM   39  O   UNK     0      35.638 -12.452   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      27.760  -1.389   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      38.128 -14.694   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      21.600  -4.056   0.000  0.00  0.00           O-1
HETATM   43  O   UNK     0      23.140  -4.056   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      20.830  -5.390   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      18.520  -6.724   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      39.944 -15.455   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      36.024  -7.287   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      33.357  -8.827   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      32.380  -5.184   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      32.380  -8.264   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      35.460  -9.391   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      26.220  -4.056   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      39.302 -10.886   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      30.840  -4.056   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      30.840  -6.724   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      33.920  -6.724   0.000  0.00  0.00           O+0
HETATM   57  P   UNK     0      34.690  -8.057   0.000  0.00  0.00           P+0
HETATM   58  P   UNK     0      32.380  -6.724   0.000  0.00  0.00           P+0
HETATM   59  H   UNK     0      20.060  -1.389   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0      24.680  -1.389   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0      17.750  -5.390   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0      29.300  -1.389   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0      36.233 -10.805   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0      26.990  -5.390   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0      36.746 -13.619   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0      26.990  -2.723   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0      39.580 -14.001   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0      29.300  -4.056   0.000  0.00  0.00           H+0
HETATM   69  H   UNK     0      40.819 -11.423   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0      29.300  -6.724   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4    5   13                                                       
CONECT    5    4   17                                                       
CONECT    6    7   16                                                       
CONECT    7    6   33                                                       
CONECT    8   14   34                                                       
CONECT    9   15   51                                                       
CONECT   10    1   23   29   59                                             
CONECT   11    2   24   52   60                                             
CONECT   12    3   30   35                                                  
CONECT   13    4   26   31   61                                             
CONECT   14    8   20   54   62                                             
CONECT   15    9   19   53   63                                             
CONECT   16    6   32   36                                                  
CONECT   17    5   37   38                                                  
CONECT   18   22   27   30   64                                             
CONECT   19   15   21   39   65                                             
CONECT   20   14   22   40   66                                             
CONECT   21   19   25   41   67                                             
CONECT   22   18   20   52   68                                             
CONECT   23   10   31   42                                                  
CONECT   24   11   29   43                                                  
CONECT   25   21   33   53   69                                             
CONECT   26   13   44   45                                                  
CONECT   27   18   54   55   70                                             
CONECT   28   32   33   46                                                  
CONECT   29   10   24                                                       
CONECT   30   12   18                                                       
CONECT   31   13   23                                                       
CONECT   32   16   28                                                       
CONECT   33    7   25   28                                                  
CONECT   34    8                                                            
CONECT   35   12                                                            
CONECT   36   16                                                            
CONECT   37   17                                                            
CONECT   38   17                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
CONECT   41   21                                                            
CONECT   42   23                                                            
CONECT   43   24                                                            
CONECT   44   26                                                            
CONECT   45   26                                                            
CONECT   46   28                                                            
CONECT   47   57                                                            
CONECT   48   57                                                            
CONECT   49   58                                                            
CONECT   50   58                                                            
CONECT   51    9   57                                                       
CONECT   52   11   22                                                       
CONECT   53   15   25                                                       
CONECT   54   14   27                                                       
CONECT   55   27   58                                                       
CONECT   56   57   58                                                       
CONECT   57   47   48   51   56                                             
CONECT   58   49   50   55   56                                             
CONECT   59   10                                                            
CONECT   60   11                                                            
CONECT   61   13                                                            
CONECT   62   14                                                            
CONECT   63   15                                                            
CONECT   64   18                                                            
CONECT   65   19                                                            
CONECT   66   20                                                            
CONECT   67   21                                                            
CONECT   68   22                                                            
CONECT   69   25                                                            
CONECT   70   27                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  144    0
END

Synonyms

Value	Source
UDP-N-Acetyl-a-D-muramoyl-L-alanyl-D-glutamate	Generator
UDP-N-Acetyl-a-D-muramoyl-L-alanyl-D-glutamic acid	Generator
UDP-N-Acetyl-alpha-D-muramoyl-L-alanyl-D-glutamic acid	Generator
UDP-N-Acetyl-α-D-muramoyl-L-alanyl-D-glutamate	Generator
UDP-N-Acetyl-α-D-muramoyl-L-alanyl-D-glutamic acid	Generator

Molecular Formula

C₂₈H₃₉N₅O₂₃P₂

Average Mass

875.582

Monoisotopic Mass

875.153300851

IUPAC Name

(4R)-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-oxidopropylidene]amino}butanoate

Traditional Name

(4R)-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-oxidopropylidene]amino}butanoate

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-])=O)C(O)=O

InChI Identifier

InChI=1S/C28H43N5O23P2/c1-10(23(42)31-13(26(44)45)4-5-17(37)38)29-24(43)11(2)52-22-18(30-12(3)35)27(54-14(8-34)20(22)40)55-58(49,50)56-57(47,48)51-9-15-19(39)21(41)25(53-15)33-7-6-16(36)32-28(33)46/h6-7,10-11,13-15,18-22,25,27,34,39-41H,4-5,8-9H2,1-3H3,(H,29,43)(H,30,35)(H,31,42)(H,37,38)(H,44,45)(H,47,48)(H,49,50)(H,32,36,46)/p-4/t10-,11+,13+,14+,15+,18+,19+,20+,21+,22+,25+,27+/m0/s1

InChI Key

OJZCATPXPWFLHF-HPUCEMLMSA-J

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
Alpha peptide
Pentose phosphate
Pentose-5-phosphate
N-acyl-alpha-hexosamine
Glutamic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Glycosyl compound
N-glycosyl compound
Alanine or derivatives
Monosaccharide phosphate
Organic pyrophosphate
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
Pyrimidone
Dicarboxylic acid or derivatives
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Alkyl phosphate
Oxane
Phosphoric acid ester
Pyrimidine
Vinylogous amide
Tetrahydrofuran
Acetamide
Heteroaromatic compound
Urea
Carboxamide group
Lactam
Secondary carboxylic acid amide
Secondary alcohol
Ether
Carboxylic acid derivative
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Azacycle
Carboxylic acid
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

UDP-N-acetylmuramoyl-L-alanyl-D-glutamate(4-) (CHEBI:83900 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-3.2	ChemAxon
pKa (Strongest Acidic)	1.71	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	24	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	447.49 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	222.65 m³·mol⁻¹	ChemAxon
Polarizability	75.1 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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0013529	Adenosine triphosphate	ADP	UDP-N-acetylmuramoylalanine--D-glutamate ligase	Ligation	RHEA	34755880
MMDBr0013707	Adenosine triphosphate	ADP	UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--L-lysine ligase	Ligation	RHEA	34755880
MMDBr0014366	Adenosine triphosphate	ADP	UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--2,6-diaminopimelate ligase	Ligation	RHEA	34755880
MMDBr0014535	Adenosine triphosphate	ADP	UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase	Ligation	RHEA	34755880
MMDBr0016954	Adenosine triphosphate	Adenosine monophosphate	UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-L-glutamate epimerase	Epimerization	RHEA	34755880
MMDBr0016955	Adenosine triphosphate	Adenosine monophosphate	UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-L-glutamate epimerase	Epimerization	RHEA	34755880

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
Bacteria	Cyanobacteria	28	Human
Bacteria	Firmicutes	150	Human feces; Human ; Cattle ; Human subgingival plaque; Human saliva
Bacteria	Proteobacteria	228	Human ; Human feces; Cattle ; Turkey ; Pig ; Sheep ; Chicken
Bacteria	Acidobacteria	3
Bacteria	Aquificae	2
Bacteria	Bacteroidetes	10	Human ; Human feces
Bacteria	Actinobacteria	34	Human ; Human feces; Cattle
Bacteria	Spirochaetes	8	Human
Bacteria	Chlamydiae	10	Human ; Sheep ; Cat
Bacteria	Chlorobi	10
Bacteria	Deinococcus-thermus	4
Bacteria/NULL	Proteobacteria	2	Human ; Human feces; Cattle ; Turkey ; Pig ; Sheep ; Chicken
Bacteria	Elusimicrobia	1
Bacteria	Thermotogae	9
Bacteria	Fusobacteria	1	Human ; Human feces
Bacteria	Chloroflexi	2
Bacteria	nah	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

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

34448896

KEGG Compound ID

Not Available

BioCyc ID

UDP-AA-GLUTAMATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25243858

PDB ID

Not Available

ChEBI ID

83900

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-D-glutamic acid (MMDBc0056359)

MOL for #<Metabolite:0x00007fa4944b4840>

3D MOL for #<Metabolite:0x00007fa4944b4840>

3D SDF for #<Metabolite:0x00007fa4944b4840>

3D-SDF for #<Metabolite:0x00007fa4944b4840>

PDB for #<Metabolite:0x00007fa4944b4840>

3D PDB for #<Metabolite:0x00007fa4944b4840>

SMILES for #<Metabolite:0x00007fa4944b4840>

INCHI for #<Metabolite:0x00007fa4944b4840>

Structure for #<Metabolite:0x00007fa4944b4840>

3D Structure for #<Metabolite:0x00007fa4944b4840>