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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:05:28 UTC

Update Date

2021-09-26 23:04:41 UTC

HMDB ID

HMDB0252240

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Fexinidazole

Description

Fexinidazole belongs to the class of organic compounds known as nitroimidazoles. Nitroimidazoles are compounds containing an imidazole ring which bears a nitro group. Based on a literature review very few articles have been published on Fexinidazole. This compound has been identified in human blood as reported by (PMID: 31557052 ). Fexinidazole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Fexinidazole 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

HMDB0252240
     RDKit          3D
Fexinidazole
 32 33  0  0  0  0  0  0  0  0999 V2000
   -6.2510    0.0501    0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5174   -0.9792   -0.9001 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7555   -0.7568   -0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1918    0.2502   -1.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8084    0.4529   -1.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0212   -0.3652   -0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3416   -0.1174   -0.7953 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1811   -0.9469    0.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5601   -0.4865   -0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029   -0.9739   -1.1040 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5848   -0.3476   -1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4783    0.5824    0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4890    1.4607    0.4328 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.6026    1.4618   -0.1078 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2321    2.3224    1.4612 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.2093    0.4572    0.4904 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    1.2480    1.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5666   -1.3775   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9480   -1.5590   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3982    1.0514   -0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1848   -0.4175    0.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5103    0.1125    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7776    0.9174   -2.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3572    1.2445   -2.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0546   -2.0075   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8885   -0.8209    1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4516   -0.5346   -1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491    2.2912    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3780    1.2946    2.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6837    0.8508    1.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459   -2.0181    0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4196   -2.3395    0.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
  6 18  1  0
 18 19  2  0
 19  3  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
  8 26  1  0
 11 27  1  0
 17 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
M  CHG  2  13   1  15  -1
M  END


  Mrv1652310201623452D          

 19 20  0  0  0  0            999 V2000
    1.4289   -1.6500    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
    2.0964   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -3.7445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0231   -2.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362   -3.2570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4208   -3.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0339   -3.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186   -3.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9901   -2.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770   -1.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5924   -2.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7747   -2.2373    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9462   -1.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810   -2.7050    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.0525   -1.8980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4941   -3.2570    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  CHG  2  17   1  19  -1
M  END
> <DATABASE_ID>
HMDB0252240

> <DATABASE_NAME>
hmdb

> <SMILES>
CSC1=CC=C(OCC2=NC=C(N2C)[N+]([O-])=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H13N3O3S/c1-14-11(13-7-12(14)15(16)17)8-18-9-3-5-10(19-2)6-4-9/h3-7H,8H2,1-2H3

> <INCHI_KEY>
MIWWSGDADVMLTG-UHFFFAOYSA-N

> <FORMULA>
C12H13N3O3S

> <MOLECULAR_WEIGHT>
279.31

> <EXACT_MASS>
279.067762465

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.530451557113555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-2-{[4-(methylsulfanyl)phenoxy]methyl}-5-nitro-1H-imidazole

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
2.3759124986666675

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.028418015405252

> <JCHEM_POLAR_SURFACE_AREA>
70.19

> <JCHEM_REFRACTIVITY>
72.645

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fexinidazole

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252240
     RDKit          3D
Fexinidazole
 32 33  0  0  0  0  0  0  0  0999 V2000
   -6.2510    0.0501    0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5174   -0.9792   -0.9001 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7555   -0.7568   -0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1918    0.2502   -1.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8084    0.4529   -1.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0212   -0.3652   -0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3416   -0.1174   -0.7953 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1811   -0.9469    0.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5601   -0.4865   -0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029   -0.9739   -1.1040 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5848   -0.3476   -1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4783    0.5824    0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4890    1.4607    0.4328 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.6026    1.4618   -0.1078 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2321    2.3224    1.4612 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.2093    0.4572    0.4904 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    1.2480    1.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5666   -1.3775   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9480   -1.5590   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3982    1.0514   -0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1848   -0.4175    0.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5103    0.1125    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7776    0.9174   -2.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3572    1.2445   -2.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0546   -2.0075   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8885   -0.8209    1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4516   -0.5346   -1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491    2.2912    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3780    1.2946    2.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6837    0.8508    1.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459   -2.0181    0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4196   -2.3395    0.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
  6 18  1  0
 18 19  2  0
 19  3  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
  8 26  1  0
 11 27  1  0
 17 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
M  CHG  2  13   1  15  -1
M  END

HEADER    PROTEIN                                 20-OCT-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-OCT-16         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.913  -5.525   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.437  -6.990   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.897  -6.990   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.421  -5.525   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.043  -5.049   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.188  -6.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.652  -5.604   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.797  -6.634   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.261  -6.158   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.581  -4.652   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.437  -3.622   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.972  -4.098   0.000  0.00  0.00           C+0
HETATM   15  S   UNK     0      -7.046  -4.176   0.000  0.00  0.00           S+0
HETATM   16  C   UNK     0      -7.366  -2.670   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.378  -5.049   0.000  0.00  0.00           N+1
HETATM   18  O   UNK     0       5.698  -3.543   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.522  -6.080   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   12   16                                                       
CONECT   16   15                                                            
CONECT   17    3   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0252240
HETATM    1  C1  UNL     1      -6.251   0.050   0.415  1.00  0.00           C  
HETATM    2  S1  UNL     1      -5.517  -0.979  -0.900  1.00  0.00           S  
HETATM    3  C2  UNL     1      -3.755  -0.757  -0.838  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.192   0.250  -1.589  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.808   0.453  -1.564  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.021  -0.365  -0.781  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.342  -0.117  -0.795  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.181  -0.947   0.005  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.560  -0.486  -0.183  1.00  0.00           C  
HETATM   10  N1  UNL     1       3.403  -0.974  -1.104  1.00  0.00           N  
HETATM   11  C8  UNL     1       4.585  -0.348  -1.023  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.478   0.582   0.004  1.00  0.00           C  
HETATM   13  N2  UNL     1       5.489   1.461   0.433  1.00  0.00           N1+
HETATM   14  O2  UNL     1       6.603   1.462  -0.108  1.00  0.00           O  
HETATM   15  O3  UNL     1       5.232   2.322   1.461  1.00  0.00           O1-
HETATM   16  N3  UNL     1       3.209   0.457   0.490  1.00  0.00           N  
HETATM   17  C10 UNL     1       2.666   1.248   1.583  1.00  0.00           C  
HETATM   18  C11 UNL     1      -1.567  -1.377  -0.023  1.00  0.00           C  
HETATM   19  C12 UNL     1      -2.948  -1.559  -0.065  1.00  0.00           C  
HETATM   20  H1  UNL     1      -6.398   1.051  -0.002  1.00  0.00           H  
HETATM   21  H2  UNL     1      -7.185  -0.418   0.800  1.00  0.00           H  
HETATM   22  H3  UNL     1      -5.510   0.112   1.237  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.778   0.917  -2.220  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.357   1.245  -2.153  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.055  -2.008  -0.312  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.889  -0.821   1.067  1.00  0.00           H  
HETATM   27  H8  UNL     1       5.452  -0.535  -1.641  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.449   2.291   1.208  1.00  0.00           H  
HETATM   29  H10 UNL     1       3.378   1.295   2.445  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.684   0.851   1.901  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.946  -2.018   0.591  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.420  -2.340   0.512  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   23
CONECT    5    6    6   24
CONECT    6    7   18
CONECT    7    8
CONECT    8    9   25   26
CONECT    9   10   10   16
CONECT   10   11
CONECT   11   12   12   27
CONECT   12   13   16
CONECT   13   14   14   15
CONECT   16   17
CONECT   17   28   29   30
CONECT   18   19   19   31
CONECT   19   32
END

HMDB0252240
     RDKit          3D
Fexinidazole
 32 33  0  0  0  0  0  0  0  0999 V2000
   -6.2510    0.0501    0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5174   -0.9792   -0.9001 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7555   -0.7568   -0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1918    0.2502   -1.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8084    0.4529   -1.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0212   -0.3652   -0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3416   -0.1174   -0.7953 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1811   -0.9469    0.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5601   -0.4865   -0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029   -0.9739   -1.1040 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5848   -0.3476   -1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4783    0.5824    0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4890    1.4607    0.4328 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.6026    1.4618   -0.1078 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2321    2.3224    1.4612 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.2093    0.4572    0.4904 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    1.2480    1.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5666   -1.3775   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9480   -1.5590   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3982    1.0514   -0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1848   -0.4175    0.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5103    0.1125    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7776    0.9174   -2.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3572    1.2445   -2.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0546   -2.0075   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8885   -0.8209    1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4516   -0.5346   -1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491    2.2912    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3780    1.2946    2.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6837    0.8508    1.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459   -2.0181    0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4196   -2.3395    0.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
  6 18  1  0
 18 19  2  0
 19  3  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
  8 26  1  0
 11 27  1  0
 17 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
M  CHG  2  13   1  15  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
HOE 239	MeSH

Chemical Formula

C₁₂H₁₃N₃O₃S

Average Molecular Weight

279.31

Monoisotopic Molecular Weight

279.067762465

IUPAC Name

1-methyl-2-{[4-(methylsulfanyl)phenoxy]methyl}-5-nitro-1H-imidazole

Traditional Name

fexinidazole

CAS Registry Number

Not Available

SMILES

CSC1=CC=C(OCC2=NC=C(N2C)[N+]([O-])=O)C=C1

InChI Identifier

InChI=1S/C12H13N3O3S/c1-14-11(13-7-12(14)15(16)17)8-18-9-3-5-10(19-2)6-4-9/h3-7H,8H2,1-2H3

InChI Key

MIWWSGDADVMLTG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitroimidazoles. Nitroimidazoles are compounds containing an imidazole ring which bears a nitro group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Nitroimidazoles

Alternative Parents

Substituents

1,2,5-trisubstituted-imidazole
Phenoxy compound
Aryl thioether
Nitroaromatic compound
Nitroimidazole
Phenol ether
Trisubstituted imidazole
Thiophenol ether
Alkyl aryl ether
Alkylarylthioether
Monocyclic benzene moiety
N-substituted imidazole
Benzenoid
Heteroaromatic compound
C-nitro compound
Organic nitro compound
Ether
Azacycle
Organic oxoazanium
Organic 1,3-dipolar compound
Thioether
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Sulfenyl compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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	2.28	ALOGPS
logP	2.38	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	1.03	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	70.19 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	72.64 m³·mol⁻¹	ChemAxon
Polarizability	28.53 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]+	160.818	30932474
DeepCCS	[M-H]-	158.179	30932474
DeepCCS	[M-2H]-	191.944	30932474
DeepCCS	[M+Na]+	168.316	30932474
AllCCS	[M+H]+	162.2	32859911
AllCCS	[M+H-H2O]+	158.7	32859911
AllCCS	[M+NH4]+	165.5	32859911
AllCCS	[M+Na]+	166.4	32859911
AllCCS	[M-H]-	162.5	32859911
AllCCS	[M+Na-2H]-	162.2	32859911
AllCCS	[M+HCOO]-	162.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fexinidazole	CSC1=CC=C(OCC2=NC=C(N2C)[N+]([O-])=O)C=C1	3146.7	Standard polar	33892256
Fexinidazole	CSC1=CC=C(OCC2=NC=C(N2C)[N+]([O-])=O)C=C1	2388.6	Standard non polar	33892256
Fexinidazole	CSC1=CC=C(OCC2=NC=C(N2C)[N+]([O-])=O)C=C1	2490.2	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 - Fexinidazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-5960000000-1a2afbed3cec3c85a061	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fexinidazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fexinidazole 10V, Positive-QTOF	splash10-001i-0090000000-35015bda73a438e02432	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fexinidazole 20V, Positive-QTOF	splash10-05gi-0090000000-f1594a195f812dea8192	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fexinidazole 40V, Positive-QTOF	splash10-0kmr-9620000000-abb060105242ead34e62	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fexinidazole 10V, Negative-QTOF	splash10-004j-6090000000-faa54d094d8b356bff5c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fexinidazole 20V, Negative-QTOF	splash10-0092-9370000000-bf91049664b340197a4f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fexinidazole 40V, Negative-QTOF	splash10-0002-9000000000-cf335fbd1993d3633672	2017-07-26	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

DB12265

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

62032

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fexinidazole

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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 Fexinidazole (HMDB0252240)

MOL for HMDB0252240 (Fexinidazole)

3D MOL for HMDB0252240 (Fexinidazole)

3D SDF for HMDB0252240 (Fexinidazole)

3D-SDF for HMDB0252240 (Fexinidazole)

PDB for HMDB0252240 (Fexinidazole)

3D PDB for HMDB0252240 (Fexinidazole)

SMILES for HMDB0252240 (Fexinidazole)

INCHI for HMDB0252240 (Fexinidazole)

Structure for HMDB0252240 (Fexinidazole)

3D Structure for HMDB0252240 (Fexinidazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra