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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:28:15 UTC

Update Date

2021-09-26 23:15:53 UTC

HMDB ID

HMDB0258745

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tauromustine

Description

Tauromustine, also known as TCNU, belongs to the class of organic compounds known as nitrosoureas. Nitrosoureas are compounds containing a nitro group and an urea group N-N linked together, with the general structure R1N(R2)C(=O)N(R3)N=O. Based on a literature review a small amount of articles have been published on Tauromustine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tauromustine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tauromustine 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

HMDB0258745
     RDKit          3D
Tauromustine
 32 31  0  0  0  0  0  0  0  0999 V2000
   -4.2179    0.2854   -0.7524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0079   -0.6341    0.3719 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8694    0.2069    1.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5449   -1.4721    0.0916 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.6830   -2.2128   -1.2083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3480   -2.4736    1.2050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433   -0.3671    0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0694   -1.1832   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947   -0.4300   -0.3129 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312    0.3734    0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2309    0.4849    1.7778 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327    1.0702    0.5054 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372    0.9664   -0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7262   -0.1934   -0.7312 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9151    0.0282    0.5443 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5954    1.8750    1.4988 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212    3.1048    1.4097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7078   -0.2366   -1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2822    0.7058   -1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8818    1.1211   -0.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4471   -0.4259    2.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8758    0.5758    1.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2065    1.0763    1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3004    0.3073   -0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462    0.2251    0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0849   -1.8424   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003   -1.8812    0.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8092   -0.5202   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    0.9584   -1.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3910    1.8785   -0.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1980   -1.1697   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1963   -0.2012   -1.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  2  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
M  END

  Mrv1652309112122282D          

 17 16  0  0  0  0            999 V2000
   -1.0974    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    2.2539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    1.8414    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7441    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  2  0  0  0  0
  4  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  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258745

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)S(=O)(=O)CCNC(=O)N(CCCl)N=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H15ClN4O4S/c1-11(2)17(15,16)6-4-9-7(13)12(10-14)5-3-8/h3-6H2,1-2H3,(H,9,13)

> <INCHI_KEY>
RCLLNBVPCJDIPX-UHFFFAOYSA-N

> <FORMULA>
C7H15ClN4O4S

> <MOLECULAR_WEIGHT>
286.73

> <EXACT_MASS>
286.0502539

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.643738213512407

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-chloroethyl)-1-[2-(dimethylsulfamoyl)ethyl]-3-nitrosourea

> <ALOGPS_LOGP>
-0.05

> <JCHEM_LOGP>
-0.7490666720000002

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.628261733554513

> <JCHEM_PKA_STRONGEST_BASIC>
-5.3447137008279935

> <JCHEM_POLAR_SURFACE_AREA>
99.15

> <JCHEM_REFRACTIVITY>
63.651500000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-chloroethyl)-1-[2-(dimethylsulfamoyl)ethyl]-3-nitrosourea

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258745
     RDKit          3D
Tauromustine
 32 31  0  0  0  0  0  0  0  0999 V2000
   -4.2179    0.2854   -0.7524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0079   -0.6341    0.3719 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8694    0.2069    1.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5449   -1.4721    0.0916 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.6830   -2.2128   -1.2083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3480   -2.4736    1.2050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433   -0.3671    0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0694   -1.1832   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947   -0.4300   -0.3129 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312    0.3734    0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2309    0.4849    1.7778 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327    1.0702    0.5054 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372    0.9664   -0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7262   -0.1934   -0.7312 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9151    0.0282    0.5443 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5954    1.8750    1.4988 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212    3.1048    1.4097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7078   -0.2366   -1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2822    0.7058   -1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8818    1.1211   -0.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4471   -0.4259    2.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8758    0.5758    1.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2065    1.0763    1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3004    0.3073   -0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462    0.2251    0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0849   -1.8424   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003   -1.8812    0.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8092   -0.5202   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    0.9584   -1.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3910    1.8785   -0.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1980   -1.1697   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1963   -0.2012   -1.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  2  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
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      -2.048   3.437   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.715   4.207   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -0.715   5.747   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       0.619   3.437   0.000  0.00  0.00           S+0
HETATM    5  O   UNK     0      -0.151   2.104   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.389   4.771   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.953   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.620   2.667   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       7.287   2.667   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      11.288   3.437   0.000  0.00  0.00          Cl+0
HETATM   16  N   UNK     0       7.287   1.127   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       8.621   0.357   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   12   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0258745
HETATM    1  C1  UNL     1      -4.218   0.285  -0.752  1.00  0.00           C  
HETATM    2  N1  UNL     1      -4.008  -0.634   0.372  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.869   0.207   1.551  1.00  0.00           C  
HETATM    4  S1  UNL     1      -2.545  -1.472   0.092  1.00  0.00           S  
HETATM    5  O1  UNL     1      -2.683  -2.213  -1.208  1.00  0.00           O  
HETATM    6  O2  UNL     1      -2.348  -2.474   1.205  1.00  0.00           O  
HETATM    7  C3  UNL     1      -1.143  -0.367   0.018  1.00  0.00           C  
HETATM    8  C4  UNL     1       0.069  -1.183  -0.227  1.00  0.00           C  
HETATM    9  N2  UNL     1       1.295  -0.430  -0.313  1.00  0.00           N  
HETATM   10  C5  UNL     1       1.831   0.373   0.683  1.00  0.00           C  
HETATM   11  O3  UNL     1       1.231   0.485   1.778  1.00  0.00           O  
HETATM   12  N3  UNL     1       3.033   1.070   0.505  1.00  0.00           N  
HETATM   13  C6  UNL     1       3.737   0.966  -0.747  1.00  0.00           C  
HETATM   14  C7  UNL     1       4.726  -0.193  -0.731  1.00  0.00           C  
HETATM   15 CL1  UNL     1       5.915   0.028   0.544  1.00  0.00          CL  
HETATM   16  N4  UNL     1       3.595   1.875   1.499  1.00  0.00           N  
HETATM   17  O4  UNL     1       3.421   3.105   1.410  1.00  0.00           O  
HETATM   18  H1  UNL     1      -4.708  -0.237  -1.603  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.282   0.706  -1.130  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.882   1.121  -0.468  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.447  -0.426   2.345  1.00  0.00           H  
HETATM   22  H5  UNL     1      -4.876   0.576   1.852  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.206   1.076   1.301  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.300   0.307  -0.856  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.146   0.225   0.928  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.085  -1.842  -1.095  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.200  -1.881   0.653  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.809  -0.520  -1.231  1.00  0.00           H  
HETATM   29  H12 UNL     1       3.098   0.958  -1.641  1.00  0.00           H  
HETATM   30  H13 UNL     1       4.391   1.879  -0.863  1.00  0.00           H  
HETATM   31  H14 UNL     1       4.198  -1.170  -0.648  1.00  0.00           H  
HETATM   32  H15 UNL     1       5.196  -0.201  -1.747  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4
CONECT    3   21   22   23
CONECT    4    5    5    6    6
CONECT    4    7
CONECT    7    8   24   25
CONECT    8    9   26   27
CONECT    9   10   28
CONECT   10   11   11   12
CONECT   12   13   16
CONECT   13   14   29   30
CONECT   14   15   31   32
CONECT   16   17   17
END

HMDB0258745
     RDKit          3D
Tauromustine
 32 31  0  0  0  0  0  0  0  0999 V2000
   -4.2179    0.2854   -0.7524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0079   -0.6341    0.3719 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8694    0.2069    1.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5449   -1.4721    0.0916 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.6830   -2.2128   -1.2083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3480   -2.4736    1.2050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433   -0.3671    0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0694   -1.1832   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947   -0.4300   -0.3129 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312    0.3734    0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2309    0.4849    1.7778 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327    1.0702    0.5054 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372    0.9664   -0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7262   -0.1934   -0.7312 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9151    0.0282    0.5443 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5954    1.8750    1.4988 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212    3.1048    1.4097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7078   -0.2366   -1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2822    0.7058   -1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8818    1.1211   -0.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4471   -0.4259    2.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8758    0.5758    1.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2065    1.0763    1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3004    0.3073   -0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462    0.2251    0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0849   -1.8424   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003   -1.8812    0.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8092   -0.5202   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    0.9584   -1.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3910    1.8785   -0.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1980   -1.1697   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1963   -0.2012   -1.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  2  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(2-Chloroethyl)-2-(dimethylsulfamoyl)-N-nitrosoethane-1-carbamimidate	HMDB
N-(2-Chloroethyl)-2-(dimethylsulphamoyl)-N-nitrosoethane-1-carbamimidate	HMDB
N-(2-Chloroethyl)-2-(dimethylsulphamoyl)-N-nitrosoethane-1-carbamimidic acid	HMDB
1-(2-Chloroethyl)-3-(2-(dimethylaminosulfonyl)ethyl)-1-nitrosourea	HMDB
TCNU	HMDB

Chemical Formula

C₇H₁₅ClN₄O₄S

Average Molecular Weight

286.73

Monoisotopic Molecular Weight

286.0502539

IUPAC Name

3-(2-chloroethyl)-1-[2-(dimethylsulfamoyl)ethyl]-3-nitrosourea

Traditional Name

3-(2-chloroethyl)-1-[2-(dimethylsulfamoyl)ethyl]-3-nitrosourea

CAS Registry Number

Not Available

SMILES

CN(C)S(=O)(=O)CCNC(=O)N(CCCl)N=O

InChI Identifier

InChI=1S/C7H15ClN4O4S/c1-11(2)17(15,16)6-4-9-7(13)12(10-14)5-3-8/h3-6H2,1-2H3,(H,9,13)

InChI Key

RCLLNBVPCJDIPX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrosoureas. Nitrosoureas are compounds containing a nitro group and an urea group N-N linked together, with the general structure R1N(R2)C(=O)N(R3)N=O.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic carbonic acids and derivatives

Sub Class

Ureas

Direct Parent

Nitrosoureas

Alternative Parents

Substituents

Nitrosourea
Organic sulfonic acid amide
Organosulfonic acid amide
Semicarbazide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Nitrosamide
Aminosulfonyl compound
Sulfonyl
Organic n-nitroso compound
Organic nitroso compound
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Carbonyl group
Alkyl halide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	-0.05	ALOGPS
logP	-0.75	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.63	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.15 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	63.65 m³·mol⁻¹	ChemAxon
Polarizability	26.64 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	153.304	30932474
DeepCCS	[M-H]-	150.946	30932474
DeepCCS	[M-2H]-	184.462	30932474
DeepCCS	[M+Na]+	159.509	30932474
AllCCS	[M+H]+	159.4	32859911
AllCCS	[M+H-H2O]+	156.5	32859911
AllCCS	[M+NH4]+	162.0	32859911
AllCCS	[M+Na]+	162.8	32859911
AllCCS	[M-H]-	157.4	32859911
AllCCS	[M+Na-2H]-	158.4	32859911
AllCCS	[M+HCOO]-	159.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tauromustine	CN(C)S(=O)(=O)CCNC(=O)N(CCCl)N=O	3027.2	Standard polar	33892256
Tauromustine	CN(C)S(=O)(=O)CCNC(=O)N(CCCl)N=O	1699.9	Standard non polar	33892256
Tauromustine	CN(C)S(=O)(=O)CCNC(=O)N(CCCl)N=O	2315.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tauromustine,1TMS,isomer #1	CN(C)S(=O)(=O)CCN(C(=O)N(CCCl)N=O)[Si](C)(C)C	2186.2	Semi standard non polar	33892256
Tauromustine,1TMS,isomer #1	CN(C)S(=O)(=O)CCN(C(=O)N(CCCl)N=O)[Si](C)(C)C	2391.1	Standard non polar	33892256
Tauromustine,1TMS,isomer #1	CN(C)S(=O)(=O)CCN(C(=O)N(CCCl)N=O)[Si](C)(C)C	3702.1	Standard polar	33892256
Tauromustine,1TBDMS,isomer #1	CN(C)S(=O)(=O)CCN(C(=O)N(CCCl)N=O)[Si](C)(C)C(C)(C)C	2428.7	Semi standard non polar	33892256
Tauromustine,1TBDMS,isomer #1	CN(C)S(=O)(=O)CCN(C(=O)N(CCCl)N=O)[Si](C)(C)C(C)(C)C	2657.3	Standard non polar	33892256
Tauromustine,1TBDMS,isomer #1	CN(C)S(=O)(=O)CCN(C(=O)N(CCCl)N=O)[Si](C)(C)C(C)(C)C	3674.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tauromustine GC-MS (Non-derivatized) - 70eV, Positive	splash10-005c-6900000000-bc2a7a5f8da8e5738ee8	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tauromustine 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

50078

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

55456

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 Tauromustine (HMDB0258745)

MOL for HMDB0258745 (Tauromustine)

3D MOL for HMDB0258745 (Tauromustine)

3D SDF for HMDB0258745 (Tauromustine)

3D-SDF for HMDB0258745 (Tauromustine)

PDB for HMDB0258745 (Tauromustine)

3D PDB for HMDB0258745 (Tauromustine)

SMILES for HMDB0258745 (Tauromustine)

INCHI for HMDB0258745 (Tauromustine)

Structure for HMDB0258745 (Tauromustine)

3D Structure for HMDB0258745 (Tauromustine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra