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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:27:25 UTC

Update Date

2021-09-26 22:55:31 UTC

HMDB ID

HMDB0246437

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Hydroperoxycyclophosphamide

Description

4-hydroperoxycyclophosphamide, also known as perfosfamide (unspecified), belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom. 4-hydroperoxycyclophosphamide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 4-hydroperoxycyclophosphamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-hydroperoxycyclophosphamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Hydroperoxycyclophosphamide 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

HMDB0256340
     RDKit          3D
Perfosfamide
 31 31  0  0  0  0  0  0  0  0999 V2000
   -0.2273   -0.8563   -1.6111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0162   -0.2395   -0.2513 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5187   -0.0675    0.6010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6253   -0.8108    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6050   -2.2858    0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3736   -3.1422   -0.6375 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8038    1.3512    0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0968    1.9999   -0.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4074    3.7378   -0.2519 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0897   -1.1221    0.7549 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4228   -0.6509    0.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1971   -1.1376   -0.2525 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2979   -1.6837    0.2740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5268    0.8695    0.6843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0068    1.1678   -0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    1.3222   -0.5801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5140   -0.4686    0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9331   -0.4497   -0.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634   -2.5672    1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5999   -2.6709   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9199    1.8180    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6886    1.4320    1.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0368    1.5262   -0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638    1.9314   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479   -2.1381    0.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8911   -0.9367    1.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9511   -0.9178    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537    1.1981    0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8924    1.3994    1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2779    0.3185   -1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4985    2.0736   -1.1536 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
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  END

  Mrv1572004221606342D          

 16 16  0  0  0  0            999 V2000
    1.1168   -0.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4630    3.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919    3.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4630    2.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919    2.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9293   -0.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8347    0.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7485    3.4200    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6064    3.4200    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3650    1.0882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1774    1.7700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5081   -0.0325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9899    1.0882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4596    0.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0222    0.5995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1774    0.9450    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  1  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 11  5  1  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  2  0  0  0  0
 16 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246437

> <DATABASE_NAME>
hmdb

> <SMILES>
OOC1CCOP(=O)(N1)N(CCCl)CCCl

> <INCHI_IDENTIFIER>
InChI=1S/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(13)10-7(15-12)1-6-14-16/h7,12H,1-6H2,(H,10,13)

> <INCHI_KEY>
VPAWVRUHMJVRHU-UHFFFAOYSA-N

> <FORMULA>
C7H15Cl2N2O4P

> <MOLECULAR_WEIGHT>
293.08

> <EXACT_MASS>
292.0146494

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
25.334850180678792

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[bis(2-chloroethyl)amino]-4-hydroperoxy-1,3,2λ⁵-oxazaphosphinan-2-one

> <ALOGPS_LOGP>
0.19

> <JCHEM_LOGP>
0.39200250433333345

> <ALOGPS_LOGS>
-1.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.741144003903868

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.889882807436798

> <JCHEM_PKA_STRONGEST_BASIC>
0.004582313118567605

> <JCHEM_POLAR_SURFACE_AREA>
71.03

> <JCHEM_REFRACTIVITY>
60.444599999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroperoxycyclophosphamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256340
     RDKit          3D
Perfosfamide
 31 31  0  0  0  0  0  0  0  0999 V2000
   -0.2273   -0.8563   -1.6111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0162   -0.2395   -0.2513 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5187   -0.0675    0.6010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6253   -0.8108    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6050   -2.2858    0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3736   -3.1422   -0.6375 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8038    1.3512    0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0968    1.9999   -0.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4074    3.7378   -0.2519 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0897   -1.1221    0.7549 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4228   -0.6509    0.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1971   -1.1376   -0.2525 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2979   -1.6837    0.2740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5268    0.8695    0.6843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0068    1.1678   -0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    1.3222   -0.5801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5140   -0.4686    0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9331   -0.4497   -0.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634   -2.5672    1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5999   -2.6709   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9199    1.8180    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6886    1.4320    1.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0368    1.5262   -0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638    1.9314   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479   -2.1381    0.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8911   -0.9367    1.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9511   -0.9178    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537    1.1981    0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8924    1.3994    1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2779    0.3185   -1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4985    2.0736   -1.1536 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
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       2.085  -0.595   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.731   5.614   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.398   5.614   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.731   4.074   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.398   4.074   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.601  -0.863   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.558   0.852   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       1.397   6.384   0.000  0.00  0.00          Cl+0
HETATM    9 Cl   UNK     0       6.732   6.384   0.000  0.00  0.00          Cl+0
HETATM   10  N   UNK     0       2.548   2.031   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       4.065   3.304   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      -0.948  -0.061   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.581   2.031   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.591   0.317   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.041   1.119   0.000  0.00  0.00           O+0
HETATM   16  P   UNK     0       4.065   1.764   0.000  0.00  0.00           P+0
CONECT    1    6    7                                                       
CONECT    2    4    8                                                       
CONECT    3    5    9                                                       
CONECT    4    2   11                                                       
CONECT    5    3   11                                                       
CONECT    6    1   14                                                       
CONECT    7    1   10   15                                                  
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    7   16                                                       
CONECT   11    4    5   16                                                  
CONECT   12   15                                                            
CONECT   13   16                                                            
CONECT   14    6   16                                                       
CONECT   15    7   12                                                       
CONECT   16   10   11   13   14                                             
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0255783
HETATM    1  O1  UNL     1      -0.093  -1.669   1.658  1.00  0.00           O  
HETATM    2  P1  UNL     1       0.235  -0.542   0.741  1.00  0.00           P  
HETATM    3  N1  UNL     1      -1.163   0.200   0.008  1.00  0.00           N  
HETATM    4  C1  UNL     1      -1.732  -0.596  -0.999  1.00  0.00           C  
HETATM    5  C2  UNL     1      -2.258  -1.942  -0.681  1.00  0.00           C  
HETATM    6 CL1  UNL     1      -3.591  -2.029   0.454  1.00  0.00          CL  
HETATM    7  C3  UNL     1      -2.076   0.713   0.958  1.00  0.00           C  
HETATM    8  C4  UNL     1      -3.041   1.728   0.347  1.00  0.00           C  
HETATM    9 CL2  UNL     1      -2.173   3.105  -0.351  1.00  0.00          CL  
HETATM   10  N2  UNL     1       1.359  -0.999  -0.535  1.00  0.00           N  
HETATM   11  C5  UNL     1       2.484  -0.054  -0.506  1.00  0.00           C  
HETATM   12  O2  UNL     1       2.026   1.247  -0.699  1.00  0.00           O  
HETATM   13  O3  UNL     1       2.572   1.778  -1.770  1.00  0.00           O  
HETATM   14  C6  UNL     1       3.236  -0.158   0.796  1.00  0.00           C  
HETATM   15  C7  UNL     1       2.313  -0.112   1.992  1.00  0.00           C  
HETATM   16  O4  UNL     1       1.129   0.593   1.663  1.00  0.00           O  
HETATM   17  H1  UNL     1      -2.583   0.003  -1.446  1.00  0.00           H  
HETATM   18  H2  UNL     1      -0.980  -0.748  -1.837  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.469  -2.680  -0.401  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.648  -2.365  -1.661  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.648  -0.038   1.470  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.525   1.293   1.753  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.687   2.091   1.186  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.756   1.256  -0.367  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.964  -0.942  -1.485  1.00  0.00           H  
HETATM   26  H10 UNL     1       3.138  -0.310  -1.353  1.00  0.00           H  
HETATM   27  H11 UNL     1       3.313   2.395  -1.467  1.00  0.00           H  
HETATM   28  H12 UNL     1       3.819  -1.090   0.855  1.00  0.00           H  
HETATM   29  H13 UNL     1       3.939   0.693   0.870  1.00  0.00           H  
HETATM   30  H14 UNL     1       2.833   0.338   2.860  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.065  -1.158   2.248  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10   16
CONECT    3    4    7
CONECT    4    5   17   18
CONECT    5    6   19   20
CONECT    7    8   21   22
CONECT    8    9   23   24
CONECT   10   11   25
CONECT   11   12   14   26
CONECT   12   13
CONECT   13   27
CONECT   14   15   28   29
CONECT   15   16   30   31
END

HMDB0256340
     RDKit          3D
Perfosfamide
 31 31  0  0  0  0  0  0  0  0999 V2000
   -0.2273   -0.8563   -1.6111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0162   -0.2395   -0.2513 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5187   -0.0675    0.6010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6253   -0.8108    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6050   -2.2858    0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3736   -3.1422   -0.6375 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8038    1.3512    0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0968    1.9999   -0.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4074    3.7378   -0.2519 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0897   -1.1221    0.7549 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4228   -0.6509    0.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1971   -1.1376   -0.2525 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2979   -1.6837    0.2740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5268    0.8695    0.6843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0068    1.1678   -0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    1.3222   -0.5801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5140   -0.4686    0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9331   -0.4497   -0.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634   -2.5672    1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5999   -2.6709   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9199    1.8180    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6886    1.4320    1.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0368    1.5262   -0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638    1.9314   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479   -2.1381    0.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8911   -0.9367    1.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9511   -0.9178    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537    1.1981    0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8924    1.3994    1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2779    0.3185   -1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4985    2.0736   -1.1536 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
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(Bis(2-chloroethyl)amino)-4-hydroperoxytetrahydro-2H-1,3,2-oxazaphosphorine	ChEBI
2-(Bis(2-chloroethyl)amino)tetrahydro-2-oxideo-2H-1,3,2-oxazaphosphorin-4-yl hydroperoxide	ChEBI
4-Hydroperoxycyclofosfamide	ChEBI
4-OOH Cyclophosphamide	ChEBI
Perfosfamide (unspecified)	ChEBI
4-Hydroperoxycyclophosphamide	MeSH
Perfosfamide	MeSH

Chemical Formula

C₇H₁₅Cl₂N₂O₄P

Average Molecular Weight

293.08

Monoisotopic Molecular Weight

292.0146494

IUPAC Name

2-[bis(2-chloroethyl)amino]-4-hydroperoxy-1,3,2λ⁵-oxazaphosphinan-2-one

Traditional Name

4-hydroperoxycyclophosphamide

CAS Registry Number

Not Available

SMILES

OOC1CCOP(=O)(N1)N(CCCl)CCCl

InChI Identifier

InChI=1S/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(13)10-7(15-12)1-6-14-16/h7,12H,1-6H2,(H,10,13)

InChI Key

VPAWVRUHMJVRHU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Nitrogen mustard compounds

Direct Parent

Nitrogen mustard compounds

Alternative Parents

Substituents

Nitrogen mustard
Phosphoric monoester diamide
Organic phosphoric acid derivative
Oxazaphosphinane
Organic phosphoric acid amide
Hydroperoxide
Alkyl hydroperoxide
Peroxol
Oxacycle
Organoheterocyclic compound
Azacycle
Organic oxide
Organooxygen compound
Organochloride
Organopnictogen compound
Alkyl chloride
Hydrocarbon derivative
Alkyl halide
Organic oxygen compound
Organohalogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:196991 )
nitrogen mustard (CHEBI:196991 )
phosphorodiamide (CHEBI:196991 )
peroxol (CHEBI:196991 )

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	0.19	ALOGPS
logP	0.39	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.89	ChemAxon
pKa (Strongest Basic)	0.0046	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	71.03 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	60.44 m³·mol⁻¹	ChemAxon
Polarizability	25.33 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	153.681	30932474
DeepCCS	[M-H]-	151.323	30932474
DeepCCS	[M-2H]-	186.039	30932474
DeepCCS	[M+Na]+	160.686	30932474
AllCCS	[M+H]+	158.4	32859911
AllCCS	[M+H-H2O]+	155.2	32859911
AllCCS	[M+NH4]+	161.4	32859911
AllCCS	[M+Na]+	162.3	32859911
AllCCS	[M-H]-	155.1	32859911
AllCCS	[M+Na-2H]-	155.9	32859911
AllCCS	[M+HCOO]-	156.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroperoxycyclophosphamide	OOC1CCOP(=O)(N1)N(CCCl)CCCl	2021.1	Standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroperoxycyclophosphamide,1TMS,isomer #1	C[Si](C)(C)N1C(OO)CCOP1(=O)N(CCCl)CCCl	2207.9	Semi standard non polar	33892256
4-Hydroperoxycyclophosphamide,1TMS,isomer #1	C[Si](C)(C)N1C(OO)CCOP1(=O)N(CCCl)CCCl	2074.5	Standard non polar	33892256
4-Hydroperoxycyclophosphamide,1TMS,isomer #1	C[Si](C)(C)N1C(OO)CCOP1(=O)N(CCCl)CCCl	3076.9	Standard polar	33892256
4-Hydroperoxycyclophosphamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(OO)CCOP1(=O)N(CCCl)CCCl	2463.4	Semi standard non polar	33892256
4-Hydroperoxycyclophosphamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(OO)CCOP1(=O)N(CCCl)CCCl	2313.3	Standard non polar	33892256
4-Hydroperoxycyclophosphamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(OO)CCOP1(=O)N(CCCl)CCCl	3204.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroperoxycyclophosphamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pec-5890000000-808432ae142e06a30ee4	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroperoxycyclophosphamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroperoxycyclophosphamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroperoxycyclophosphamide 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 - 4-Hydroperoxycyclophosphamide 10V, Positive-QTOF	splash10-0006-7290000000-369e529e47644e69c6ab	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxycyclophosphamide 20V, Positive-QTOF	splash10-0006-8900000000-90b368d14388c79fb509	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxycyclophosphamide 40V, Positive-QTOF	splash10-0006-9100000000-d4eb56956140223874f6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxycyclophosphamide 10V, Negative-QTOF	splash10-004l-3590000000-3f1b1200044cc3c1b169	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxycyclophosphamide 20V, Negative-QTOF	splash10-01p9-9000000000-841c60362349bbc8be68	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxycyclophosphamide 40V, Negative-QTOF	splash10-0007-9000000000-963533f3ff1adae026b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxycyclophosphamide 10V, Positive-QTOF	splash10-0a4l-0190000000-c343d0d4d93b705a5f58	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxycyclophosphamide 20V, Positive-QTOF	splash10-0btc-5930000000-62d2c1c9134013a5b09a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxycyclophosphamide 40V, Positive-QTOF	splash10-06xx-9500000000-e0df3ca5200bb192a83f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxycyclophosphamide 10V, Negative-QTOF	splash10-0006-0090000000-03b80a4ce1cf39d1232f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxycyclophosphamide 20V, Negative-QTOF	splash10-0006-0190000000-e484481cc7bee075914a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroperoxycyclophosphamide 40V, Negative-QTOF	splash10-003r-9310000000-50b58dac039a8c783b29	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

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

35147

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Perfosfamide

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

196991

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 4-Hydroperoxycyclophosphamide (HMDB0246437)

MOL for HMDB0246437 (4-Hydroperoxycyclophosphamide)

3D MOL for HMDB0246437 (4-Hydroperoxycyclophosphamide)

3D SDF for HMDB0246437 (4-Hydroperoxycyclophosphamide)

3D-SDF for HMDB0246437 (4-Hydroperoxycyclophosphamide)

PDB for HMDB0246437 (4-Hydroperoxycyclophosphamide)

3D PDB for HMDB0246437 (4-Hydroperoxycyclophosphamide)

SMILES for HMDB0246437 (4-Hydroperoxycyclophosphamide)

INCHI for HMDB0246437 (4-Hydroperoxycyclophosphamide)

Structure for HMDB0246437 (4-Hydroperoxycyclophosphamide)

3D Structure for HMDB0246437 (4-Hydroperoxycyclophosphamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra