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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:04:31 UTC

Update Date

2021-09-26 23:08:50 UTC

HMDB ID

HMDB0254688

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Metronidazole benzoate

Description

Metronidazole benzoate, also known as benzoylmetronidazole or elyzol, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Based on a literature review a significant number of articles have been published on Metronidazole benzoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Metronidazole benzoate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Metronidazole benzoate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254688
     RDKit          3D
Metronidazole benzoate
 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.3968    1.2054    1.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556    0.2727    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9646    0.1723    0.2179 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9156   -0.7614   -0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6138   -1.2555   -0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1638   -2.2753   -1.5841 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.9865   -2.6597   -1.5228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0266   -2.8258   -2.4859 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.9000   -0.6103    0.2276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5108   -0.8010    0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6825    0.1061   -0.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7084   -0.0128    0.0100 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    0.7224   -0.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2553    1.5227   -1.5419 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0965    0.6123   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0205    1.3649   -1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902    1.2633   -0.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8273    0.3917    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8995   -0.3726    0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5384   -0.2576    0.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8786    2.0921    1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3174    1.5664    2.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7987    0.6779    2.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7047   -1.0934   -1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146   -0.5266    1.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1920   -1.8329    0.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9182   -0.0901   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9531    1.1565   -0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677    2.0453   -1.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1112    1.8706   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8639    0.2559    0.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2023   -1.0734    1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8432   -0.8503    1.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  9  2  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  CHG  2   6   1   8  -1
M  END

  Mrv1652309112116042D          

 20 21  0  0  0  0            999 V2000
   -0.9021   -3.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152   -3.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3221   -3.4670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7346   -2.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1826   -2.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3541   -1.3325    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -3.1388   -1.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7410   -0.7804    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  CHG  2  18   1  20  -1
M  END
> <DATABASE_ID>
HMDB0254688

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NC=C(N1CCOC(=O)C1=CC=CC=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H13N3O4/c1-10-14-9-12(16(18)19)15(10)7-8-20-13(17)11-5-3-2-4-6-11/h2-6,9H,7-8H2,1H3

> <INCHI_KEY>
CUUCCLJJOWSASK-UHFFFAOYSA-N

> <FORMULA>
C13H13N3O4

> <MOLECULAR_WEIGHT>
275.264

> <EXACT_MASS>
275.090605911

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.68287607844859

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
2.035989624

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.570682981358693

> <JCHEM_POLAR_SURFACE_AREA>
87.26

> <JCHEM_REFRACTIVITY>
70.0383

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
metrogyl

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254688
     RDKit          3D
Metronidazole benzoate
 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.3968    1.2054    1.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556    0.2727    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9646    0.1723    0.2179 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9156   -0.7614   -0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6138   -1.2555   -0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1638   -2.2753   -1.5841 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.9865   -2.6597   -1.5228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0266   -2.8258   -2.4859 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.9000   -0.6103    0.2276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5108   -0.8010    0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6825    0.1061   -0.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7084   -0.0128    0.0100 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    0.7224   -0.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2553    1.5227   -1.5419 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0965    0.6123   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0205    1.3649   -1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902    1.2633   -0.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8273    0.3917    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8995   -0.3726    0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5384   -0.2576    0.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8786    2.0921    1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3174    1.5664    2.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7987    0.6779    2.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7047   -1.0934   -1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146   -0.5266    1.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1920   -1.8329    0.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9182   -0.0901   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9531    1.1565   -0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677    2.0453   -1.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1112    1.8706   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8639    0.2559    0.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2023   -1.0734    1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8432   -0.8503    1.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  9  2  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  CHG  2   6   1   8  -1
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -1.684  -7.182   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.828  -6.152   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -4.335  -6.472   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -5.105  -5.138   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.074  -3.994   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -2.667  -4.620   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -4.394  -2.487   0.000  0.00  0.00           N+1
HETATM   19  O   UNK     0      -5.859  -2.011   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.250  -1.457   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    5   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0254688
HETATM    1  C1  UNL     1      -3.397   1.205   1.890  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.756   0.273   0.795  1.00  0.00           C  
HETATM    3  N1  UNL     1      -4.965   0.172   0.218  1.00  0.00           N  
HETATM    4  C3  UNL     1      -4.916  -0.761  -0.718  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.614  -1.255  -0.713  1.00  0.00           C  
HETATM    6  N2  UNL     1      -3.164  -2.275  -1.584  1.00  0.00           N1+
HETATM    7  O1  UNL     1      -1.986  -2.660  -1.523  1.00  0.00           O  
HETATM    8  O2  UNL     1      -4.027  -2.826  -2.486  1.00  0.00           O1-
HETATM    9  N3  UNL     1      -2.900  -0.610   0.228  1.00  0.00           N  
HETATM   10  C5  UNL     1      -1.511  -0.801   0.586  1.00  0.00           C  
HETATM   11  C6  UNL     1      -0.682   0.106  -0.273  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.708  -0.013   0.010  1.00  0.00           O  
HETATM   13  C7  UNL     1       1.669   0.722  -0.653  1.00  0.00           C  
HETATM   14  O4  UNL     1       1.255   1.523  -1.542  1.00  0.00           O  
HETATM   15  C8  UNL     1       3.097   0.612  -0.375  1.00  0.00           C  
HETATM   16  C9  UNL     1       4.021   1.365  -1.061  1.00  0.00           C  
HETATM   17  C10 UNL     1       5.390   1.263  -0.799  1.00  0.00           C  
HETATM   18  C11 UNL     1       5.827   0.392   0.167  1.00  0.00           C  
HETATM   19  C12 UNL     1       4.900  -0.373   0.865  1.00  0.00           C  
HETATM   20  C13 UNL     1       3.538  -0.258   0.589  1.00  0.00           C  
HETATM   21  H1  UNL     1      -2.879   2.092   1.475  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.317   1.566   2.391  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.799   0.678   2.666  1.00  0.00           H  
HETATM   24  H4  UNL     1      -5.705  -1.093  -1.368  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.415  -0.527   1.683  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.192  -1.833   0.466  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.918  -0.090  -1.320  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.953   1.157  -0.017  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.668   2.045  -1.817  1.00  0.00           H  
HETATM   30  H10 UNL     1       6.111   1.871  -1.355  1.00  0.00           H  
HETATM   31  H11 UNL     1       6.864   0.256   0.428  1.00  0.00           H  
HETATM   32  H12 UNL     1       5.202  -1.073   1.636  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.843  -0.850   1.133  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3    9
CONECT    3    4
CONECT    4    5    5   24
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    9   10
CONECT   10   11   25   26
CONECT   11   12   27   28
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16   16   20
CONECT   16   17   29
CONECT   17   18   18   30
CONECT   18   19   31
CONECT   19   20   20   32
CONECT   20   33
END

HMDB0254688
     RDKit          3D
Metronidazole benzoate
 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.3968    1.2054    1.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556    0.2727    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9646    0.1723    0.2179 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9156   -0.7614   -0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6138   -1.2555   -0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1638   -2.2753   -1.5841 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.9865   -2.6597   -1.5228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0266   -2.8258   -2.4859 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.9000   -0.6103    0.2276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5108   -0.8010    0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6825    0.1061   -0.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7084   -0.0128    0.0100 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    0.7224   -0.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2553    1.5227   -1.5419 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0965    0.6123   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0205    1.3649   -1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902    1.2633   -0.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8273    0.3917    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8995   -0.3726    0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5384   -0.2576    0.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8786    2.0921    1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3174    1.5664    2.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7987    0.6779    2.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7047   -1.0934   -1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146   -0.5266    1.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1920   -1.8329    0.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9182   -0.0901   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9531    1.1565   -0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677    2.0453   -1.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1112    1.8706   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8639    0.2559    0.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2023   -1.0734    1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8432   -0.8503    1.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  9  2  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  CHG  2   6   1   8  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Methyl-5-nitro-1H-imidazole-1-ethyl benzoate	ChEBI
Benzoylmetronidazole	ChEBI
Elyzol	ChEBI
Flagyl S	ChEBI
Flegyl	ChEBI
Vertisal	ChEBI
2-Methyl-5-nitro-1H-imidazole-1-ethyl benzoic acid	Generator
Metronidazole benzoic acid	Generator
Klion suspension	HMDB
Benzoylmetronidazole monohydrate	HMDB

Chemical Formula

C₁₃H₁₃N₃O₄

Average Molecular Weight

275.264

Monoisotopic Molecular Weight

275.090605911

IUPAC Name

2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate

Traditional Name

metrogyl

CAS Registry Number

Not Available

SMILES

CC1=NC=C(N1CCOC(=O)C1=CC=CC=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C13H13N3O4/c1-10-14-9-12(16(18)19)15(10)7-8-20-13(17)11-5-3-2-4-6-11/h2-6,9H,7-8H2,1H3

InChI Key

CUUCCLJJOWSASK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
1,2,5-trisubstituted-imidazole
Nitroaromatic compound
Benzoyl
Nitroimidazole
Trisubstituted imidazole
N-substituted imidazole
Azole
Heteroaromatic compound
Imidazole
Carboxylic acid ester
Organic nitro compound
C-nitro compound
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

benzoate ester (CHEBI:50688 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0254688)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.71	ALOGPS
logP	2.04	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	2.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	87.26 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.04 m³·mol⁻¹	ChemAxon
Polarizability	26.68 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	153.483	30932474
DeepCCS	[M-H]-	150.223	30932474
DeepCCS	[M-2H]-	185.552	30932474
DeepCCS	[M+Na]+	161.688	30932474
AllCCS	[M+H]+	161.7	32859911
AllCCS	[M+H-H2O]+	158.0	32859911
AllCCS	[M+NH4]+	165.1	32859911
AllCCS	[M+Na]+	166.1	32859911
AllCCS	[M-H]-	163.6	32859911
AllCCS	[M+Na-2H]-	163.2	32859911
AllCCS	[M+HCOO]-	162.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Metronidazole benzoate	CC1=NC=C(N1CCOC(=O)C1=CC=CC=C1)[N+]([O-])=O	3011.2	Standard polar	33892256
Metronidazole benzoate	CC1=NC=C(N1CCOC(=O)C1=CC=CC=C1)[N+]([O-])=O	2223.6	Standard non polar	33892256
Metronidazole benzoate	CC1=NC=C(N1CCOC(=O)C1=CC=CC=C1)[N+]([O-])=O	2289.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Metronidazole benzoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2910000000-49e7ab1cd7adb80ea7c4	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metronidazole benzoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

75079

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Metronidazole

METLIN ID

Not Available

PubChem Compound

83213

PDB ID

Not Available

ChEBI ID

50688

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Metronidazole benzoate (HMDB0254688)

MOL for HMDB0254688 (Metronidazole benzoate)

3D MOL for HMDB0254688 (Metronidazole benzoate)

3D SDF for HMDB0254688 (Metronidazole benzoate)

3D-SDF for HMDB0254688 (Metronidazole benzoate)

PDB for HMDB0254688 (Metronidazole benzoate)

3D PDB for HMDB0254688 (Metronidazole benzoate)

SMILES for HMDB0254688 (Metronidazole benzoate)

INCHI for HMDB0254688 (Metronidazole benzoate)

Structure for HMDB0254688 (Metronidazole benzoate)

3D Structure for HMDB0254688 (Metronidazole benzoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra