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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:48:31 UTC

Update Date

2021-09-26 23:16:44 UTC

HMDB ID

HMDB0259291

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Trofosfamide

Description

Trofosfamide belongs to the class of organic compounds known as isofamides. These are oxazaphospholanes containing the isofamide skeleton. Isofamide is a heterocyclic compound made up of a 1,3,2-oxazaphospholane, where the phosphorus atom is part of a phosphodiamide group, and the oxazaphospholane is substituted by two haloalkyl chains. Based on a literature review a significant number of articles have been published on Trofosfamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Trofosfamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Trofosfamide 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

HMDB0259291
     RDKit          3D
Trofosfamide
 35 35  0  0  0  0  0  0  0  0999 V2000
    0.0375    0.0187    1.9161 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0137   -0.2708    0.4408 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5826    0.1497   -0.1533 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191    1.5489    0.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5815    2.5145   -0.9957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992    2.7671   -1.4034 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4840   -0.5167    0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5556   -1.9852    0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7413   -2.5226    1.9868 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2458   -1.9414    0.2829 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102   -2.2765   -1.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8794   -1.6666   -1.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7273   -0.2160   -1.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3159    0.5423   -0.3845 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4583    0.5598    0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2940    1.6754    1.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7219    1.6317    2.5902 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4217    1.9192    1.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0134    1.6266    0.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947    2.2750   -1.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9967    3.5311   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4535    0.0001    0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0113   -0.2557    1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658   -2.5615    0.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0005   -2.3282   -0.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284   -1.7037   -1.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5056   -3.3488   -1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5408   -1.8880   -0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525   -2.1160   -2.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6833    0.2143   -1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9812   -0.0009   -2.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3628    0.6917   -0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638   -0.4277    1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3953    1.6946    2.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3617    2.6659    0.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 14  2  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
M  END


  Mrv1652306031609322D          

 17 17  0  0  0  0            999 V2000
    5.3592   -2.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2057    0.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842    1.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0131    1.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6414   -1.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3933    0.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842    0.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0131    0.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5468   -2.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4879    0.9450    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8697    1.5830    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7276    1.5830    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.1111   -0.7488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2986   -0.0670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -0.7488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0165   -1.6673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2986   -0.8920    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14  8  1  0  0  0  0
 16  9  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259291

> <DATABASE_NAME>
hmdb

> <SMILES>
ClCCN(CCCl)P1(=O)OCCCN1CCCl

> <INCHI_IDENTIFIER>
InChI=1S/C9H18Cl3N2O2P/c10-2-6-13-5-1-9-16-17(13,15)14(7-3-11)8-4-12/h1-9H2

> <INCHI_KEY>
UMKFEPPTGMDVMI-UHFFFAOYSA-N

> <FORMULA>
C9H18Cl3N2O2P

> <MOLECULAR_WEIGHT>
323.58

> <EXACT_MASS>
322.0171479

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.81477967690501

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[bis(2-chloroethyl)amino]-3-(2-chloroethyl)-1,3,2lambda5-oxazaphosphinan-2-one

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
0.9847135963333332

> <ALOGPS_LOGS>
-1.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.15039857936284384

> <JCHEM_POLAR_SURFACE_AREA>
32.78

> <JCHEM_REFRACTIVITY>
72.71809999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[bis(2-chloroethyl)amino]-3-(2-chloroethyl)-1,3,2lambda5-oxazaphosphinan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0259291
     RDKit          3D
Trofosfamide
 35 35  0  0  0  0  0  0  0  0999 V2000
    0.0375    0.0187    1.9161 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0137   -0.2708    0.4408 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5826    0.1497   -0.1533 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191    1.5489    0.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5815    2.5145   -0.9957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992    2.7671   -1.4034 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4840   -0.5167    0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5556   -1.9852    0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7413   -2.5226    1.9868 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2458   -1.9414    0.2829 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102   -2.2765   -1.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8794   -1.6666   -1.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7273   -0.2160   -1.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3159    0.5423   -0.3845 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4583    0.5598    0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2940    1.6754    1.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7219    1.6317    2.5902 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4217    1.9192    1.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0134    1.6266    0.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947    2.2750   -1.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9967    3.5311   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4535    0.0001    0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0113   -0.2557    1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658   -2.5615    0.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0005   -2.3282   -0.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284   -1.7037   -1.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5056   -3.3488   -1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5408   -1.8880   -0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525   -2.1160   -2.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6833    0.2143   -1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9812   -0.0009   -2.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3628    0.6917   -0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638   -0.4277    1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3953    1.6946    2.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3617    2.6659    0.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 14  2  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      10.004  -4.025   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.584   0.317   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.690   2.185   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.358   2.185   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.531  -2.577   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.067   0.049   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.690   0.645   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.358   0.645   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.487  -4.292   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0      12.111   1.764   0.000  0.00  0.00          Cl+0
HETATM   11 Cl   UNK     0       5.357   2.955   0.000  0.00  0.00          Cl+0
HETATM   12 Cl   UNK     0      10.691   2.955   0.000  0.00  0.00          Cl+0
HETATM   13  N   UNK     0       9.541  -1.398   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       8.024  -0.125   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       6.508  -1.398   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.497  -3.112   0.000  0.00  0.00           O+0
HETATM   17  P   UNK     0       8.024  -1.665   0.000  0.00  0.00           P+0
CONECT    1    5    9                                                       
CONECT    2    6   10                                                       
CONECT    3    7   11                                                       
CONECT    4    8   12                                                       
CONECT    5    1   13                                                       
CONECT    6    2   13                                                       
CONECT    7    3   14                                                       
CONECT    8    4   14                                                       
CONECT    9    1   16                                                       
CONECT   10    2                                                            
CONECT   11    3                                                            
CONECT   12    4                                                            
CONECT   13    5    6   17                                                  
CONECT   14    7    8   17                                                  
CONECT   15   17                                                            
CONECT   16    9   17                                                       
CONECT   17   13   14   15   16                                             
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0259291
HETATM    1  O1  UNL     1       0.038   0.019   1.916  1.00  0.00           O  
HETATM    2  P1  UNL     1       0.014  -0.271   0.441  1.00  0.00           P  
HETATM    3  N1  UNL     1      -1.583   0.150  -0.153  1.00  0.00           N  
HETATM    4  C1  UNL     1      -1.919   1.549   0.061  1.00  0.00           C  
HETATM    5  C2  UNL     1      -1.581   2.515  -0.996  1.00  0.00           C  
HETATM    6 CL1  UNL     1       0.099   2.767  -1.403  1.00  0.00          CL  
HETATM    7  C3  UNL     1      -2.484  -0.517   0.843  1.00  0.00           C  
HETATM    8  C4  UNL     1      -2.556  -1.985   0.717  1.00  0.00           C  
HETATM    9 CL2  UNL     1      -3.741  -2.523   1.987  1.00  0.00          CL  
HETATM   10  O2  UNL     1       0.246  -1.941   0.283  1.00  0.00           O  
HETATM   11  C5  UNL     1       0.510  -2.277  -1.026  1.00  0.00           C  
HETATM   12  C6  UNL     1       1.879  -1.667  -1.356  1.00  0.00           C  
HETATM   13  C7  UNL     1       1.727  -0.216  -1.570  1.00  0.00           C  
HETATM   14  N2  UNL     1       1.316   0.542  -0.385  1.00  0.00           N  
HETATM   15  C8  UNL     1       2.458   0.560   0.515  1.00  0.00           C  
HETATM   16  C9  UNL     1       2.294   1.675   1.513  1.00  0.00           C  
HETATM   17 CL3  UNL     1       3.722   1.632   2.590  1.00  0.00          CL  
HETATM   18  H1  UNL     1      -1.422   1.919   1.013  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.013   1.627   0.259  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.195   2.275  -1.947  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.997   3.531  -0.691  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.454   0.000   0.842  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.011  -0.256   1.828  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.666  -2.562   0.937  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.001  -2.328  -0.256  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.228  -1.704  -1.645  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.506  -3.349  -1.206  1.00  0.00           H  
HETATM   28  H11 UNL     1       2.541  -1.888  -0.511  1.00  0.00           H  
HETATM   29  H12 UNL     1       2.252  -2.116  -2.316  1.00  0.00           H  
HETATM   30  H13 UNL     1       2.683   0.214  -1.921  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.981  -0.001  -2.382  1.00  0.00           H  
HETATM   32  H15 UNL     1       3.363   0.692  -0.070  1.00  0.00           H  
HETATM   33  H16 UNL     1       2.464  -0.428   1.054  1.00  0.00           H  
HETATM   34  H17 UNL     1       1.395   1.695   2.097  1.00  0.00           H  
HETATM   35  H18 UNL     1       2.362   2.666   0.937  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10   14
CONECT    3    4    7
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    7    8   22   23
CONECT    8    9   24   25
CONECT   10   11
CONECT   11   12   26   27
CONECT   12   13   28   29
CONECT   13   14   30   31
CONECT   14   15
CONECT   15   16   32   33
CONECT   16   17   34   35
END

HMDB0259291
     RDKit          3D
Trofosfamide
 35 35  0  0  0  0  0  0  0  0999 V2000
    0.0375    0.0187    1.9161 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0137   -0.2708    0.4408 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5826    0.1497   -0.1533 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191    1.5489    0.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5815    2.5145   -0.9957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992    2.7671   -1.4034 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4840   -0.5167    0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5556   -1.9852    0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7413   -2.5226    1.9868 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2458   -1.9414    0.2829 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102   -2.2765   -1.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8794   -1.6666   -1.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7273   -0.2160   -1.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3159    0.5423   -0.3845 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4583    0.5598    0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2940    1.6754    1.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7219    1.6317    2.5902 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4217    1.9192    1.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0134    1.6266    0.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947    2.2750   -1.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9967    3.5311   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4535    0.0001    0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0113   -0.2557    1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658   -2.5615    0.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0005   -2.3282   -0.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284   -1.7037   -1.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5056   -3.3488   -1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5408   -1.8880   -0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525   -2.1160   -2.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6833    0.2143   -1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9812   -0.0009   -2.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3628    0.6917   -0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638   -0.4277    1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3953    1.6946    2.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3617    2.6659    0.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 14  2  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Z-4828a-4828Trophosphamide	ChEMBL
Ixoten	MeSH
N,N,N'-tris(2-chloroethyl)-n'-O-propylene phosphoric acid ester diamide	MeSH
Trophosphamide	MeSH
Genoxal trofosfamida	MeSH

Chemical Formula

C₉H₁₈Cl₃N₂O₂P

Average Molecular Weight

323.58

Monoisotopic Molecular Weight

322.0171479

IUPAC Name

2-[bis(2-chloroethyl)amino]-3-(2-chloroethyl)-1,3,2lambda5-oxazaphosphinan-2-one

Traditional Name

2-[bis(2-chloroethyl)amino]-3-(2-chloroethyl)-1,3,2lambda5-oxazaphosphinan-2-one

CAS Registry Number

Not Available

SMILES

ClCCN(CCCl)P1(=O)OCCCN1CCCl

InChI Identifier

InChI=1S/C9H18Cl3N2O2P/c10-2-6-13-5-1-9-16-17(13,15)14(7-3-11)8-4-12/h1-9H2

InChI Key

UMKFEPPTGMDVMI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isofamides. These are oxazaphospholanes containing the isofamide skeleton. Isofamide is a heterocyclic compound made up of a 1,3,2-oxazaphospholane, where the phosphorus atom is part of a phosphodiamide group, and the oxazaphospholane is substituted by two haloalkyl chains.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxazaphosphinanes

Sub Class

Isofamides

Direct Parent

Isofamides

Alternative Parents

Substituents

Isofamide
Nitrogen mustard
Phosphoric monoester diamide
Organic phosphoric acid derivative
Organic phosphoric acid amide
Azacycle
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organochloride
Organopnictogen compound
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Alkyl halide
Alkyl chloride
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	1.4	ALOGPS
logP	0.98	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	0.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	32.78 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	72.72 m³·mol⁻¹	ChemAxon
Polarizability	29.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	160.676	30932474
DeepCCS	[M-H]-	158.318	30932474
DeepCCS	[M-2H]-	192.603	30932474
DeepCCS	[M+Na]+	167.429	30932474
AllCCS	[M+H]+	162.9	32859911
AllCCS	[M+H-H2O]+	160.0	32859911
AllCCS	[M+NH4]+	165.6	32859911
AllCCS	[M+Na]+	166.4	32859911
AllCCS	[M-H]-	161.8	32859911
AllCCS	[M+Na-2H]-	162.7	32859911
AllCCS	[M+HCOO]-	163.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trofosfamide	ClCCN(CCCl)P1(=O)OCCCN1CCCl	2928.3	Standard polar	33892256
Trofosfamide	ClCCN(CCCl)P1(=O)OCCCN1CCCl	2106.6	Standard non polar	33892256
Trofosfamide	ClCCN(CCCl)P1(=O)OCCCN1CCCl	2312.3	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 - Trofosfamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01wr-1390000000-0afd21ebf3af426e20d9	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trofosfamide 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 - Trofosfamide 10V, Positive-QTOF	splash10-0006-9323000000-c915e6f1b855e99ba0a4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trofosfamide 20V, Positive-QTOF	splash10-0006-4900000000-606f1434f3fb12b4b398	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trofosfamide 40V, Positive-QTOF	splash10-01r6-9100000000-fdd511c33c062a620634	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trofosfamide 10V, Negative-QTOF	splash10-0a4j-1390000000-1f0c252d058b66c4b0b6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trofosfamide 20V, Negative-QTOF	splash10-0159-7900000000-1cee7f661aec43a3eb62	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trofosfamide 40V, Negative-QTOF	splash10-000i-5910000000-7fe3392edc1195eb4525	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	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

DB12902

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

59129

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trofosfamide

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 Trofosfamide (HMDB0259291)

MOL for HMDB0259291 (Trofosfamide)

3D MOL for HMDB0259291 (Trofosfamide)

3D SDF for HMDB0259291 (Trofosfamide)

3D-SDF for HMDB0259291 (Trofosfamide)

PDB for HMDB0259291 (Trofosfamide)

3D PDB for HMDB0259291 (Trofosfamide)

SMILES for HMDB0259291 (Trofosfamide)

INCHI for HMDB0259291 (Trofosfamide)

Structure for HMDB0259291 (Trofosfamide)

3D Structure for HMDB0259291 (Trofosfamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra