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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:42 UTC

HMDB ID

HMDB0014672

Secondary Accession Numbers

HMDB14672

Metabolite Identification

Common Name

Cyclophosphamide

Description

Cyclophosphamide, also known as cytoxan or cytophosphan, 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. In humans, cyclophosphamide is involved in the cyclophosphamide action pathway. Cyclophosphamide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Cyclophosphamide is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on Cyclophosphamide.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0242208
     RDKit          3D
(-)-Cyclophosphamide
 29 29  0  0  0  0  0  0  0  0999 V2000
   -0.2294   -1.8778   -1.5117 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2627   -0.7466   -0.6403 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.0827   -0.0079    0.1154 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8538    1.3177    0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8962    2.3408    0.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4892    2.0944    0.8449 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0341   -0.7993    0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224   -2.0903    0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6672   -2.9643    1.0640 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4418   -1.4221    0.4585 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7656   -1.0220   -0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7353    0.4935   -0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1039    0.9540   -1.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9195    0.3769   -1.7112 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1239    1.6605    0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7541    1.3462    1.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5278    3.3351    0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9383    2.4759   -0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676   -1.1179    1.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9625   -0.2441    0.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8765   -1.8903   -0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -2.7996    0.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2853   -1.2018    1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5807   -1.4063    0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8356   -1.3791   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2869    0.8833    0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8210    0.8003   -0.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9775    2.0632   -1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    0.8278   -2.1876 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  2  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
M  END

531
  Mrv1652305271900062D          

 14 14  0  0  1  0            999 V2000
    1.6500   -0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -2.2540    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    0.6040    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396    1.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376   -0.1106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -0.1106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106    1.0165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106    1.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    2.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396    1.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  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
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014672

> <DATABASE_NAME>
hmdb

> <SMILES>
ClCCN(CCCl)P1(=O)NCCCO1

> <INCHI_IDENTIFIER>
InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)

> <INCHI_KEY>
CMSMOCZEIVJLDB-UHFFFAOYSA-N

> <FORMULA>
C7H15Cl2N2O2P

> <MOLECULAR_WEIGHT>
261.086

> <EXACT_MASS>
260.02481966

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
23.722394450622833

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.76

> <JCHEM_LOGP>
0.09654768666666613

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.42654312142604

> <JCHEM_PKA_STRONGEST_BASIC>
0.0840914699297235

> <JCHEM_POLAR_SURFACE_AREA>
41.57

> <JCHEM_REFRACTIVITY>
58.47810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242208
     RDKit          3D
(-)-Cyclophosphamide
 29 29  0  0  0  0  0  0  0  0999 V2000
   -0.2294   -1.8778   -1.5117 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2627   -0.7466   -0.6403 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.0827   -0.0079    0.1154 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8538    1.3177    0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8962    2.3408    0.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4892    2.0944    0.8449 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0341   -0.7993    0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224   -2.0903    0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6672   -2.9643    1.0640 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4418   -1.4221    0.4585 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7656   -1.0220   -0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7353    0.4935   -0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1039    0.9540   -1.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9195    0.3769   -1.7112 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1239    1.6605    0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7541    1.3462    1.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5278    3.3351    0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9383    2.4759   -0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676   -1.1179    1.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9625   -0.2441    0.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8765   -1.8903   -0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -2.7996    0.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2853   -1.2018    1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5807   -1.4063    0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8356   -1.3791   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2869    0.8833    0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8210    0.8003   -0.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9775    2.0632   -1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    0.8278   -2.1876 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  2  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 531                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1 Cl   UNK     0       3.080  -1.540   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       7.700  -4.207   0.000  0.00  0.00          Cl+0
HETATM    3  P   UNK     0       7.700   1.127   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0       9.034   1.897   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.470  -0.206   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       6.930  -0.206   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       6.366   1.897   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.366   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.700   4.207   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.390  -0.206   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.700  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.620  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.930  -2.874   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3    4    5    6    7                                             
CONECT    4    3   10                                                       
CONECT    5    3                                                            
CONECT    6    3   11   12                                                  
CONECT    7    3    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    4    9                                                       
CONECT   11    6   13                                                       
CONECT   12    6   14                                                       
CONECT   13    1   11                                                       
CONECT   14    2   12                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0242208
HETATM    1  O1  UNL     1      -0.229  -1.878  -1.512  1.00  0.00           O  
HETATM    2  P1  UNL     1       0.263  -0.747  -0.640  1.00  0.00           P  
HETATM    3  N1  UNL     1      -1.083  -0.008   0.115  1.00  0.00           N  
HETATM    4  C1  UNL     1      -0.854   1.318   0.544  1.00  0.00           C  
HETATM    5  C2  UNL     1      -1.896   2.341   0.196  1.00  0.00           C  
HETATM    6 CL1  UNL     1      -3.489   2.094   0.845  1.00  0.00          CL  
HETATM    7  C3  UNL     1      -2.034  -0.799   0.757  1.00  0.00           C  
HETATM    8  C4  UNL     1      -2.422  -2.090   0.090  1.00  0.00           C  
HETATM    9 CL2  UNL     1      -3.667  -2.964   1.064  1.00  0.00          CL  
HETATM   10  N2  UNL     1       1.442  -1.422   0.459  1.00  0.00           N  
HETATM   11  C5  UNL     1       2.766  -1.022  -0.016  1.00  0.00           C  
HETATM   12  C6  UNL     1       2.735   0.494  -0.095  1.00  0.00           C  
HETATM   13  C7  UNL     1       2.104   0.954  -1.345  1.00  0.00           C  
HETATM   14  O2  UNL     1       0.920   0.377  -1.711  1.00  0.00           O  
HETATM   15  H1  UNL     1       0.124   1.660   0.130  1.00  0.00           H  
HETATM   16  H2  UNL     1      -0.754   1.346   1.667  1.00  0.00           H  
HETATM   17  H3  UNL     1      -1.528   3.335   0.589  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.938   2.476  -0.922  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.668  -1.118   1.799  1.00  0.00           H  
HETATM   20  H6  UNL     1      -2.962  -0.244   0.988  1.00  0.00           H  
HETATM   21  H7  UNL     1      -2.876  -1.890  -0.897  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.584  -2.800   0.042  1.00  0.00           H  
HETATM   23  H9  UNL     1       1.285  -1.202   1.452  1.00  0.00           H  
HETATM   24  H10 UNL     1       3.581  -1.406   0.586  1.00  0.00           H  
HETATM   25  H11 UNL     1       2.836  -1.379  -1.083  1.00  0.00           H  
HETATM   26  H12 UNL     1       2.287   0.883   0.835  1.00  0.00           H  
HETATM   27  H13 UNL     1       3.821   0.800  -0.138  1.00  0.00           H  
HETATM   28  H14 UNL     1       1.978   2.063  -1.295  1.00  0.00           H  
HETATM   29  H15 UNL     1       2.846   0.828  -2.188  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10   14
CONECT    3    4    7
CONECT    4    5   15   16
CONECT    5    6   17   18
CONECT    7    8   19   20
CONECT    8    9   21   22
CONECT   10   11   23
CONECT   11   12   24   25
CONECT   12   13   26   27
CONECT   13   14   28   29
END

HMDB0242208
     RDKit          3D
(-)-Cyclophosphamide
 29 29  0  0  0  0  0  0  0  0999 V2000
   -0.2294   -1.8778   -1.5117 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2627   -0.7466   -0.6403 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.0827   -0.0079    0.1154 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8538    1.3177    0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8962    2.3408    0.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4892    2.0944    0.8449 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0341   -0.7993    0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224   -2.0903    0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6672   -2.9643    1.0640 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4418   -1.4221    0.4585 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7656   -1.0220   -0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7353    0.4935   -0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1039    0.9540   -1.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9195    0.3769   -1.7112 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1239    1.6605    0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7541    1.3462    1.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5278    3.3351    0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9383    2.4759   -0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676   -1.1179    1.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9625   -0.2441    0.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8765   -1.8903   -0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -2.7996    0.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2853   -1.2018    1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5807   -1.4063    0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8356   -1.3791   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2869    0.8833    0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8210    0.8003   -0.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9775    2.0632   -1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    0.8278   -2.1876 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  2  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+-)-Cyclophosphamide	ChEBI
(RS)-Cyclophosphamide	ChEBI
2-[Bis(2-chloroethylamino)]-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide	ChEBI
Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester	ChEBI
Cyclophosphamide anhydrous	ChEBI
N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide	ChEBI
Cytoxan	Kegg
Cyclophosphamide monohydrate	HMDB
Cytophosphan	HMDB
Sendoxan	HMDB
Anhydrous, cyclophosphamide	HMDB
Cyclophosphamide, (S)-isomer	HMDB
Cyclophosphane	HMDB
Cytophosphane	HMDB
Endoxan	HMDB
Neosar	HMDB
Cyclophosphamide, (R)-isomer	HMDB
Monohydrate, cyclophosphamide	HMDB
Procytox	HMDB
(+,-)-2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide monohydrate	HMDB

Chemical Formula

C₇H₁₅Cl₂N₂O₂P

Average Molecular Weight

261.086

Monoisotopic Molecular Weight

260.02481966

IUPAC Name

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

Traditional Name

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

CAS Registry Number

6055-19-2

SMILES

ClCCN(CCCl)P1(=O)NCCCO1

InChI Identifier

InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)

InChI Key

CMSMOCZEIVJLDB-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
Oxacycle
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organochloride
Organopnictogen compound
Organohalogen compound
Organic oxygen compound
Alkyl chloride
Alkyl halide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:4027 )
nitrogen mustard (CHEBI:4027 )
phosphorodiamide (CHEBI:4027 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	41 - 45 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	15.1 g/L	Not Available
LogP	0.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	146.525	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000702

Predicted Molecular Properties

Property	Value	Source
Water Solubility	15.1 g/L	ALOGPS
logP	0.76	ALOGPS
logP	0.097	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	13.43	ChemAxon
pKa (Strongest Basic)	0.084	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.57 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	58.48 m³·mol⁻¹	ChemAxon
Polarizability	23.72 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]+	154.384	30932474
DeepCCS	[M-H]-	151.23	30932474
DeepCCS	[M-2H]-	187.767	30932474
DeepCCS	[M+Na]+	163.43	30932474
AllCCS	[M+H]+	152.4	32859911
AllCCS	[M+H-H2O]+	148.9	32859911
AllCCS	[M+NH4]+	155.6	32859911
AllCCS	[M+Na]+	156.5	32859911
AllCCS	[M-H]-	150.4	32859911
AllCCS	[M+Na-2H]-	151.5	32859911
AllCCS	[M+HCOO]-	152.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.32 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7753 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.07 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	75.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclophosphamide	ClCCN(CCCl)P1(=O)NCCCO1	2753.1	Standard polar	33892256
Cyclophosphamide	ClCCN(CCCl)P1(=O)NCCCO1	1805.4	Standard non polar	33892256
Cyclophosphamide	ClCCN(CCCl)P1(=O)NCCCO1	2041.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclophosphamide,1TMS,isomer #1	C[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl	2041.3	Semi standard non polar	33892256
Cyclophosphamide,1TMS,isomer #1	C[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl	1917.6	Standard non polar	33892256
Cyclophosphamide,1TMS,isomer #1	C[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl	2667.1	Standard polar	33892256
Cyclophosphamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl	2272.9	Semi standard non polar	33892256
Cyclophosphamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl	2163.3	Standard non polar	33892256
Cyclophosphamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCCOP1(=O)N(CCCl)CCCl	2799.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclophosphamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dj-2930000000-a5e2529d99bd261703f0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclophosphamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclophosphamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclophosphamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-08fr-9470000000-53f4a8ff83c415492e03	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-qTof , Positive-QTOF	splash10-0059-1490000000-36d8ebdb421248c38c7b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-qTof , Positive-QTOF	splash10-03di-1390000000-b8dc1a824ec33e388213	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-qTof , Positive-QTOF	splash10-03di-0390000000-66983035d1db7ac36bd6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-001l-0970000000-939110a705ed71803ab8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-03di-0090000000-2bdfe4296c2bdf8d4a99	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-03di-0190000000-1e8e017f8e39fa5d73cf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-0006-0930000000-d7459c8d20a8fc59f6f0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-0006-0900000000-33cb20e845200f9d2618	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-0006-2900000000-09d33a8387b9d152f24a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-01ox-6900000000-cdebe09ff6df7c25b477	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-03di-0090000000-d749f27c3144da2c431c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-03di-0190000000-a6fa921df18384671a7c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-0006-0930000000-abdb40162fc8a44200f7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-0006-0900000000-8c0705ee62a5f9c7d44e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-0006-2900000000-a299026342c77e92c48c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-01ox-6900000000-fc2845c75bbccc83ad99	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-001l-0970000000-83e0f5b88b6fbe0a1ea7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-0006-0900000000-5490a2b493bfde967fa3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclophosphamide LC-ESI-ITFT , positive-QTOF	splash10-0006-0900000000-456626f46e480e0ac670	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclophosphamide 10V, Positive-QTOF	splash10-0006-9150000000-28408c9f0486cc7568f2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclophosphamide 20V, Positive-QTOF	splash10-052f-9600000000-fd85ba5646421fb4dd68	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclophosphamide 40V, Positive-QTOF	splash10-0006-9100000000-dc67f093f2419f82cb18	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclophosphamide 10V, Negative-QTOF	splash10-0002-1920000000-ef90686fe8c9da71ccd6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclophosphamide 20V, Negative-QTOF	splash10-0a4i-9000000000-c974342f3a086d037df6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclophosphamide 40V, Negative-QTOF	splash10-002u-9600000000-142aeef910da3ef2f6b3	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Cyclophosphamide Action Pathway		Not Available
Cyclophosphamide Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00531	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00531	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00531

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2804

KEGG Compound ID

C07888

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cyclophosphamide

METLIN ID

Not Available

PubChem Compound

2907

PDB ID

Not Available

ChEBI ID

4027

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

Brock N: Oxazaphosphorine cytostatics: past-present-future. Seventh Cain Memorial Award lecture. Cancer Res. 1989 Jan 1;49(1):1-7. [PubMed:2491747 ]
Brock N: The history of the oxazaphosphorine cytostatics. Cancer. 1996 Aug 1;78(3):542-7. [PubMed:8697402 ]
(). FDA label . .

Showing metabocard for Cyclophosphamide (HMDB0014672)

MOL for HMDB0014672 (Cyclophosphamide)

3D MOL for HMDB0014672 (Cyclophosphamide)

3D SDF for HMDB0014672 (Cyclophosphamide)

3D-SDF for HMDB0014672 (Cyclophosphamide)

PDB for HMDB0014672 (Cyclophosphamide)

3D PDB for HMDB0014672 (Cyclophosphamide)

SMILES for HMDB0014672 (Cyclophosphamide)

INCHI for HMDB0014672 (Cyclophosphamide)

Structure for HMDB0014672 (Cyclophosphamide)

3D Structure for HMDB0014672 (Cyclophosphamide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra