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Showing metabocard for 2,4,6-Trinitrotoluene (HMDB0245483)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:32:56 UTC
Update Date2021-09-26 22:53:58 UTC
HMDB IDHMDB0245483
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,4,6-Trinitrotoluene
Description2,4,6-Trinitrotoluene, also known as TNT or trinitrotoluen, belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. 2,4,6-Trinitrotoluene exists in all living organisms, ranging from bacteria to humans. 2,4,6-Trinitrotoluene has been detected, but not quantified in, several different foods, such as teas (Camellia sinensis), red onion, lingonberries (Vaccinium vitis-idaea), yellow pond-lilies (Nuphar lutea), and poppies (Papaver). This could make 2,4,6-trinitrotoluene a potential biomarker for the consumption of these foods. 2,4,6-Trinitrotoluene is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 2,4,6-Trinitrotoluene. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,4,6-trinitrotoluene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,4,6-Trinitrotoluene 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0245483 (2,4,6-Trinitrotoluene)

TNL
  Mrv0541 02231215382D          

 16 16  0  0  0  0            999 V2000
    0.4705    0.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1850    0.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705   -0.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1850   -0.9607    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.1850   -1.7857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8994   -0.5482    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.2440   -0.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584   -0.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -0.9607    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.6729   -1.7857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3874   -0.5482    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.9584    0.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    0.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    1.5143    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.9584    1.9268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705    1.9268    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1 13  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  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
 14 16  1  0  0  0  0
M  CHG  6   4   1   6  -1   9   1  11  -1  14   1  16  -1
M  END
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3D MOL for HMDB0245483 (2,4,6-Trinitrotoluene)

HMDB0245483
     RDKit          3D
2,4,6-Trinitrotoluene
 21 21  0  0  0  0  0  0  0  0999 V2000
   -2.3478   -0.5391   -0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197   -0.1646   -0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4221    1.1120   -0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258    2.1596   -0.5933 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3262    2.0687   -1.2943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0318    3.4198   -0.0790 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9404    1.3991   -0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8280    0.4087    0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228    0.6527    0.3734 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.7069    1.7823    0.2603 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0310   -0.3979    0.6735 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.3368   -0.8682    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -1.1566    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4275   -2.5054    0.3266 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.2376   -3.2637    1.0917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4973   -3.0457   -0.2921 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.6458   -1.2826    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075    0.3540   -0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415   -0.8561   -1.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2805    2.4221   -0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0159   -1.6992    0.5798 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
  4  6  1  0
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  7 20  1  0
 12 21  1  0
M  CHG  6   4   1   6  -1   9   1  11  -1  14   1  16  -1
M  END
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3D SDF for HMDB0245483 (2,4,6-Trinitrotoluene)

TNL
  Mrv0541 02231215382D          

 16 16  0  0  0  0            999 V2000
    0.4705    0.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1850    0.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705   -0.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1850   -0.9607    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.1850   -1.7857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8994   -0.5482    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.2440   -0.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584   -0.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -0.9607    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.6729   -1.7857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3874   -0.5482    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.9584    0.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    0.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    1.5143    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.9584    1.9268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705    1.9268    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1 13  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  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
 14 16  1  0  0  0  0
M  CHG  6   4   1   6  -1   9   1  11  -1  14   1  16  -1
M  END
> <DATABASE_ID>
HMDB0245483

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H5N3O6/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10(15)16/h2-3H,1H3

> <INCHI_KEY>
SPSSULHKWOKEEL-UHFFFAOYSA-N

> <FORMULA>
C7H5N3O6

> <MOLECULAR_WEIGHT>
227.1311

> <EXACT_MASS>
227.017834907

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
17.897497947806563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-1,3,5-trinitrobenzene

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
2.306619773333334

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.99115470103241

> <JCHEM_POLAR_SURFACE_AREA>
137.45999999999998

> <JCHEM_REFRACTIVITY>
53.07330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-tnt

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0245483 (2,4,6-Trinitrotoluene)

HMDB0245483
     RDKit          3D
2,4,6-Trinitrotoluene
 21 21  0  0  0  0  0  0  0  0999 V2000
   -2.3478   -0.5391   -0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197   -0.1646   -0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4221    1.1120   -0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258    2.1596   -0.5933 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3262    2.0687   -1.2943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0318    3.4198   -0.0790 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9404    1.3991   -0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8280    0.4087    0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228    0.6527    0.3734 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.7069    1.7823    0.2603 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0310   -0.3979    0.6735 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.3368   -0.8682    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -1.1566    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4275   -2.5054    0.3266 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.2376   -3.2637    1.0917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4973   -3.0457   -0.2921 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.6458   -1.2826    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075    0.3540   -0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415   -0.8561   -1.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2805    2.4221   -0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0159   -1.6992    0.5798 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
  4  6  1  0
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  7 20  1  0
 12 21  1  0
M  CHG  6   4   1   6  -1   9   1  11  -1  14   1  16  -1
M  END
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PDB for HMDB0245483 (2,4,6-Trinitrotoluene)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: TNL                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.878   0.517   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.212   1.287   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.878  -1.023   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.212  -1.793   0.000  0.00  0.00           N+1
HETATM    5  O   UNK     0       2.212  -3.333   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.546  -1.023   0.000  0.00  0.00           O-1
HETATM    7  C   UNK     0      -0.455  -1.793   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.789  -1.023   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -3.123  -1.793   0.000  0.00  0.00           N+1
HETATM   10  O   UNK     0      -3.123  -3.333   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.456  -1.023   0.000  0.00  0.00           O-1
HETATM   12  C   UNK     0      -1.789   0.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.455   1.287   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -0.455   2.827   0.000  0.00  0.00           N+1
HETATM   15  O   UNK     0      -1.789   3.597   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.878   3.597   0.000  0.00  0.00           O-1
CONECT    1    2    3   13                                                  
CONECT    2    1                                                            
CONECT    3    1    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13    1   12   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END
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3D PDB for HMDB0245483 (2,4,6-Trinitrotoluene)

COMPND    HMDB0245483
HETATM    1  C1  UNL     1      -2.348  -0.539  -0.255  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.920  -0.165  -0.131  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.422   1.112  -0.269  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.326   2.160  -0.593  1.00  0.00           N1+
HETATM    5  O1  UNL     1      -2.326   2.069  -1.294  1.00  0.00           O  
HETATM    6  O2  UNL     1      -1.032   3.420  -0.079  1.00  0.00           O1-
HETATM    7  C4  UNL     1       0.940   1.399  -0.106  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.828   0.409   0.198  1.00  0.00           C  
HETATM    9  N2  UNL     1       3.223   0.653   0.373  1.00  0.00           N1+
HETATM   10  O3  UNL     1       3.707   1.782   0.260  1.00  0.00           O  
HETATM   11  O4  UNL     1       4.031  -0.398   0.674  1.00  0.00           O1-
HETATM   12  C6  UNL     1       1.337  -0.868   0.336  1.00  0.00           C  
HETATM   13  C7  UNL     1      -0.007  -1.157   0.176  1.00  0.00           C  
HETATM   14  N3  UNL     1      -0.428  -2.505   0.327  1.00  0.00           N1+
HETATM   15  O5  UNL     1       0.238  -3.264   1.092  1.00  0.00           O  
HETATM   16  O6  UNL     1      -1.497  -3.046  -0.292  1.00  0.00           O1-
HETATM   17  H1  UNL     1      -2.646  -1.283   0.529  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.007   0.354  -0.026  1.00  0.00           H  
HETATM   19  H3  UNL     1      -2.642  -0.856  -1.274  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.280   2.422  -0.225  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.016  -1.699   0.580  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3   13
CONECT    3    4    7
CONECT    4    5    5    6
CONECT    7    8    8   20
CONECT    8    9   12
CONECT    9   10   10   11
CONECT   12   13   13   21
CONECT   13   14
CONECT   14   15   15   16
END
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SMILES for HMDB0245483 (2,4,6-Trinitrotoluene)

CC1=C(C=C(C=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O
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INCHI for HMDB0245483 (2,4,6-Trinitrotoluene)

InChI=1S/C7H5N3O6/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10(15)16/h2-3H,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1-Methyl-2,4,6-trinitrobenzeneChEBI
2,4,6-TNTChEBI
2,4,6-TrinitrotoluolChEBI
alpha-TNTChEBI
S-TrinitrotolueneChEBI
S-TrinitrotoluolChEBI
Sym-trinitrotoluolChEBI
TNTChEBI
TrinitrotoluenChEBI
TrinitrotolueneChEBI
TrinitrotoluolChEBI
TritolChEBI
TrotylChEBI
a-TNTGenerator
Α-TNTGenerator
2,4,6-TrinitrotolueneKEGG
Chemical FormulaC7H5N3O6
Average Molecular Weight227.1311
Monoisotopic Molecular Weight227.017834907
IUPAC Name2-methyl-1,3,5-trinitrobenzene
Traditional Nameα-tnt
CAS Registry NumberNot Available
SMILES
CC1=C(C=C(C=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O
InChI Identifier
InChI=1S/C7H5N3O6/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10(15)16/h2-3H,1H3
InChI KeySPSSULHKWOKEEL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNitrobenzenes
Direct ParentNitrobenzenes
Alternative Parents
Substituents
  • Nitrobenzene
  • Nitrotoluene
  • Nitroaromatic compound
  • Toluene
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01676
Phenol Explorer Compound IDNot Available
FooDB IDFDB030299
KNApSAcK IDNot Available
Chemspider ID8073
KEGG Compound IDC16391
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrinitrotoluene
METLIN IDNot Available
PubChem Compound8376
PDB IDNot Available
ChEBI ID46053
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]