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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015312

Secondary Accession Numbers

HMDB15312

Metabolite Identification

Common Name

Ifosfamide

Description

Ifosfamide is only found in individuals that have used or taken this drug. It is a positional isomer of cyclophosphamide which is active as an alkylating agent and an immunosuppressive agent. [PubChem]The exact mechanism of ifosfamide has not been determined, but appears to be similar to other alkylating agents. Ifosfamide requires biotransformation in the liver by mixed-function oxidases (cytochrome P450 system) before it becomes active. After metabolic activation, active metabolites of ifosfamide alkylate or bind with many intracellular molecular structures, including nucleic acids. The cytotoxic action is primarily through the alkylation of DNA, done by attaching the N-7 position of guanine to its reactive electrophilic groups. The formation of inter and intra strand cross-links in the DNA results in cell death.

Structure

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

HMDB0015312
     RDKit          3D
Ifosfamide
 29 29  0  0  0  0  0  0  0  0999 V2000
    0.2546   -0.5541    2.0267 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0322    0.1114    0.6949 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4000   -0.3055   -0.3225 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647   -0.2771    0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8504   -0.5709   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    0.6283   -1.4469 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1684    1.7932    0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4951    2.5584    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9510    2.1793   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0280    0.8374   -0.8091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4828   -0.2069   -0.0002 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7880   -1.5165   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783   -2.6078    0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619   -4.1611   -0.1858 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4807    0.4079   -1.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276   -1.1161    1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471    0.6767    1.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6741   -0.5179    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8280   -1.5706   -0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4451    3.6058    0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0070    2.5231   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4663    2.1094    0.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4159    2.9291   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0993    0.6341   -0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5136    0.8801   -1.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8855   -1.6147   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3315   -1.7600   -1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -2.5152    1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -2.5798    0.8169 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
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11  2  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
M  END

1181
  Mrv1652305271900162D          

 14 14  0  0  1  0            999 V2000
    1.6500    0.6040    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.2540    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6040    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205   -0.1106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955   -0.1106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955   -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  8  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  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>
HMDB0015312

> <DATABASE_NAME>
hmdb

> <SMILES>
ClCCNP1(=O)OCCCN1CCCl

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

> <INCHI_KEY>
HOMGKSMUEGBAAB-UHFFFAOYSA-N

> <FORMULA>
C7H15Cl2N2O2P

> <MOLECULAR_WEIGHT>
261.086

> <EXACT_MASS>
260.02481966

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
23.943197490268794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.57

> <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>
14.588063611240123

> <JCHEM_PKA_STRONGEST_BASIC>
-0.0303482447921688

> <JCHEM_POLAR_SURFACE_AREA>
41.57

> <JCHEM_REFRACTIVITY>
58.47810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015312
     RDKit          3D
Ifosfamide
 29 29  0  0  0  0  0  0  0  0999 V2000
    0.2546   -0.5541    2.0267 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0322    0.1114    0.6949 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4000   -0.3055   -0.3225 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647   -0.2771    0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8504   -0.5709   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    0.6283   -1.4469 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1684    1.7932    0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4951    2.5584    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9510    2.1793   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0280    0.8374   -0.8091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4828   -0.2069   -0.0002 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7880   -1.5165   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783   -2.6078    0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619   -4.1611   -0.1858 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4807    0.4079   -1.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276   -1.1161    1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471    0.6767    1.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6741   -0.5179    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8280   -1.5706   -0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4451    3.6058    0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0070    2.5231   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4663    2.1094    0.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4159    2.9291   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0993    0.6341   -0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5136    0.8801   -1.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8855   -1.6147   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3315   -1.7600   -1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -2.5152    1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -2.5798    0.8169 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
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11  2  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 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: 1181                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1 Cl   UNK     0       3.080   1.127   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       8.415  -4.207   0.000  0.00  0.00          Cl+0
HETATM    3  P   UNK     0       8.415   1.127   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0       9.748   1.897   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.185  -0.206   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       7.081   1.897   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       7.645  -0.206   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.081   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415   4.207   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748   1.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   1.897   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.645  -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    8   11                                                  
CONECT    7    3   12                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    4    9                                                       
CONECT   11    6   13                                                       
CONECT   12    7   14                                                       
CONECT   13    1   11                                                       
CONECT   14    2   12                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0015312
HETATM    1  O1  UNL     1       0.255  -0.554   2.027  1.00  0.00           O  
HETATM    2  P1  UNL     1       0.032   0.111   0.695  1.00  0.00           P  
HETATM    3  N1  UNL     1       1.400  -0.306  -0.323  1.00  0.00           N  
HETATM    4  C1  UNL     1       2.565  -0.277   0.568  1.00  0.00           C  
HETATM    5  C2  UNL     1       3.850  -0.571  -0.159  1.00  0.00           C  
HETATM    6 CL1  UNL     1       4.139   0.628  -1.447  1.00  0.00          CL  
HETATM    7  O2  UNL     1       0.168   1.793   0.979  1.00  0.00           O  
HETATM    8  C3  UNL     1      -0.495   2.558   0.069  1.00  0.00           C  
HETATM    9  C4  UNL     1      -1.951   2.179  -0.101  1.00  0.00           C  
HETATM   10  C5  UNL     1      -2.028   0.837  -0.809  1.00  0.00           C  
HETATM   11  N2  UNL     1      -1.483  -0.207  -0.000  1.00  0.00           N  
HETATM   12  C6  UNL     1      -1.788  -1.516  -0.408  1.00  0.00           C  
HETATM   13  C7  UNL     1      -1.378  -2.608   0.553  1.00  0.00           C  
HETATM   14 CL2  UNL     1      -1.862  -4.161  -0.186  1.00  0.00          CL  
HETATM   15  H1  UNL     1       1.481   0.408  -1.061  1.00  0.00           H  
HETATM   16  H2  UNL     1       2.428  -1.116   1.301  1.00  0.00           H  
HETATM   17  H3  UNL     1       2.647   0.677   1.105  1.00  0.00           H  
HETATM   18  H4  UNL     1       4.674  -0.518   0.599  1.00  0.00           H  
HETATM   19  H5  UNL     1       3.828  -1.571  -0.604  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.445   3.606   0.444  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.007   2.523  -0.917  1.00  0.00           H  
HETATM   22  H8  UNL     1      -2.466   2.109   0.880  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.416   2.929  -0.764  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.099   0.634  -0.984  1.00  0.00           H  
HETATM   25  H11 UNL     1      -1.514   0.880  -1.787  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.886  -1.615  -0.557  1.00  0.00           H  
HETATM   27  H13 UNL     1      -1.332  -1.760  -1.415  1.00  0.00           H  
HETATM   28  H14 UNL     1      -2.005  -2.515   1.484  1.00  0.00           H  
HETATM   29  H15 UNL     1      -0.327  -2.580   0.817  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7   11
CONECT    3    4   15
CONECT    4    5   16   17
CONECT    5    6   18   19
CONECT    7    8
CONECT    8    9   20   21
CONECT    9   10   22   23
CONECT   10   11   24   25
CONECT   11   12
CONECT   12   13   26   27
CONECT   13   14   28   29
END

HMDB0015312
     RDKit          3D
Ifosfamide
 29 29  0  0  0  0  0  0  0  0999 V2000
    0.2546   -0.5541    2.0267 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0322    0.1114    0.6949 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4000   -0.3055   -0.3225 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647   -0.2771    0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8504   -0.5709   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    0.6283   -1.4469 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1684    1.7932    0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4951    2.5584    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9510    2.1793   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0280    0.8374   -0.8091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4828   -0.2069   -0.0002 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7880   -1.5165   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783   -2.6078    0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619   -4.1611   -0.1858 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4807    0.4079   -1.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276   -1.1161    1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471    0.6767    1.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6741   -0.5179    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8280   -1.5706   -0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4451    3.6058    0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0070    2.5231   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4663    2.1094    0.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4159    2.9291   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0993    0.6341   -0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5136    0.8801   -1.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8855   -1.6147   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3315   -1.7600   -1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -2.5152    1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -2.5798    0.8169 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
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11  2  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 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
3-(2-Chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide	ChEBI
Ifosfamida	ChEBI
Ifosfamidum	ChEBI
Iphosphamide	ChEBI
Isofosfamide	ChEBI
Isophosphamide	ChEBI
Isosfamide	ChEBI
Ifex	Kegg
Asta Z 4942	HMDB
I-phosphamide	HMDB
Ifosfamid	HMDB
Ifosfamide sterile	HMDB
Ifosphamide	HMDB
Ifsofamide	HMDB
Iphosphamid	HMDB
Iso-endoxan	HMDB
Iso endoxan	HMDB
Holoxan	HMDB

Chemical Formula

C₇H₁₅Cl₂N₂O₂P

Average Molecular Weight

261.086

Monoisotopic Molecular Weight

260.02481966

IUPAC Name

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

Traditional Name

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

CAS Registry Number

3778-73-2

SMILES

ClCCNP1(=O)OCCCN1CCCl

InChI Identifier

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

InChI Key

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

ifosfamides (CHEBI:5864 )

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

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	39 - 41 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	15 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	147.0	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001035

Predicted Molecular Properties

Property	Value	Source
Water Solubility	15 g/L	ALOGPS
logP	0.57	ALOGPS
logP	0.097	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	14.59	ChemAxon
pKa (Strongest Basic)	-0.03	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	23.94 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]+	144.33	30932474
DeepCCS	[M-H]-	141.425	30932474
DeepCCS	[M-2H]-	177.711	30932474
DeepCCS	[M+Na]+	153.248	30932474
AllCCS	[M+H]+	152.4	32859911
AllCCS	[M+H-H2O]+	149.0	32859911
AllCCS	[M+NH4]+	155.6	32859911
AllCCS	[M+Na]+	156.5	32859911
AllCCS	[M-H]-	151.1	32859911
AllCCS	[M+Na-2H]-	152.3	32859911
AllCCS	[M+HCOO]-	153.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ifosfamide	ClCCNP1(=O)OCCCN1CCCl	2677.2	Standard polar	33892256
Ifosfamide	ClCCNP1(=O)OCCCN1CCCl	1826.8	Standard non polar	33892256
Ifosfamide	ClCCNP1(=O)OCCCN1CCCl	2035.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ifosfamide,1TMS,isomer #1	C[Si](C)(C)N(CCCl)P1(=O)OCCCN1CCCl	2026.9	Semi standard non polar	33892256
Ifosfamide,1TMS,isomer #1	C[Si](C)(C)N(CCCl)P1(=O)OCCCN1CCCl	1945.5	Standard non polar	33892256
Ifosfamide,1TMS,isomer #1	C[Si](C)(C)N(CCCl)P1(=O)OCCCN1CCCl	2809.4	Standard polar	33892256
Ifosfamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCCN1CCCl	2268.5	Semi standard non polar	33892256
Ifosfamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCCN1CCCl	2188.5	Standard non polar	33892256
Ifosfamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCCN1CCCl	2948.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ifosfamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-03gj-3950000000-d61f04c75e5216d6c481	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ifosfamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ifosfamide 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-qTof , Positive-QTOF	splash10-001i-0290000000-4c400c6848932e5bc304	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-qTof , Positive-QTOF	splash10-03di-1390000000-cb6bb34e3efac3f15b24	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-qTof , Positive-QTOF	splash10-0udi-3910000000-2729bcf5701a78198ad5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOF	splash10-001i-0490000000-17ba12fd0e00df2723dc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOF	splash10-03di-0090000000-d4e1a660175509162e8c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOF	splash10-03di-0090000000-c26cb9c6b0b1cafbc7c2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOF	splash10-0gx3-6960000000-e4f4eadda4e355e7dd84	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOF	splash10-0f6x-8900000000-10d5b2623785719eb1e7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOF	splash10-0006-9500000000-d06de43b506b64b21f31	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOF	splash10-0006-9300000000-698d7a6ed4f1837ad721	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOF	splash10-03di-0090000000-084cc16ffb95bd0ef960	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOF	splash10-03di-0090000000-1ae1b6f01a6e1a37e34c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOF	splash10-0gx3-6960000000-ad40c4b969e8d0286677	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOF	splash10-0f6x-8900000000-137610f53c637d8d5b79	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOF	splash10-0006-9500000000-6b78178980477a0f7c08	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOF	splash10-0006-9200000000-e6f6b95f30fc4c9fde8a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOF	splash10-001i-0490000000-661cabcd304902a3d4b5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide , positive-QTOF	splash10-001i-0290000000-4c400c6848932e5bc304	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ifosfamide , positive-QTOF	splash10-03di-1390000000-cb6bb34e3efac3f15b24	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifosfamide 10V, Positive-QTOF	splash10-0006-9030000000-82608eec100a23f0266e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifosfamide 20V, Positive-QTOF	splash10-001i-9100000000-755c8d4c9c0f9d89400e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifosfamide 40V, Positive-QTOF	splash10-0006-9000000000-8b8aed41746e222fd47a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifosfamide 10V, Negative-QTOF	splash10-0002-1910000000-ddc3d173bfc120e5f7dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifosfamide 20V, Negative-QTOF	splash10-0159-8900000000-e4192b3d1839133ffa5e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ifosfamide 40V, Negative-QTOF	splash10-004i-9000000000-7de8be0f841d92b19769	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Ifosfamide Action Pathway		Not Available
Ifosfamide 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 DB01181	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01181	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 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

DB01181

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3562

KEGG Compound ID

C07047

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ifosfamide

METLIN ID

Not Available

PubChem Compound

3690

PDB ID

Not Available

ChEBI ID

5864

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

Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
Allen LM, Creaven PJ, Nelson RL: Studies on the human pharmacokinetics of isophosphamide (NSC-109724). Cancer Treat Rep. 1976 Apr;60(4):451-8. [PubMed:1277221 ]
Dechant KL, Brogden RN, Pilkington T, Faulds D: Ifosfamide/mesna. A review of its antineoplastic activity, pharmacokinetic properties and therapeutic efficacy in cancer. Drugs. 1991 Sep;42(3):428-67. [PubMed:1720382 ]
Schoenike SE, Dana WJ: Ifosfamide and mesna. Clin Pharm. 1990 Mar;9(3):179-91. [PubMed:2107997 ]
Zalupski M, Baker LH: Ifosfamide. J Natl Cancer Inst. 1988 Jun 15;80(8):556-66. [PubMed:3286879 ]
Brade WP, Herdrich K, Varini M: Ifosfamide--pharmacology, safety and therapeutic potential. Cancer Treat Rev. 1985 Mar;12(1):1-47. [PubMed:3896483 ]
Wagner T: Ifosfamide clinical pharmacokinetics. Clin Pharmacokinet. 1994 Jun;26(6):439-56. [PubMed:8070218 ]
Fleming RA: An overview of cyclophosphamide and ifosfamide pharmacology. Pharmacotherapy. 1997 Sep-Oct;17(5 Pt 2):146S-154S. [PubMed:9322882 ]
Furlanut M, Franceschi L: Pharmacology of ifosfamide. Oncology. 2003;65 Suppl 2:2-6. [PubMed:14586139 ]
Willits I, Price L, Parry A, Tilby MJ, Ford D, Cholerton S, Pearson AD, Boddy AV: Pharmacokinetics and metabolism of ifosfamide in relation to DNA damage assessed by the COMET assay in children with cancer. Br J Cancer. 2005 May 9;92(9):1626-35. [PubMed:15827549 ]
(). FDA label . .

Showing metabocard for Ifosfamide (HMDB0015312)

MOL for HMDB0015312 (Ifosfamide)

3D MOL for HMDB0015312 (Ifosfamide)

3D SDF for HMDB0015312 (Ifosfamide)

3D-SDF for HMDB0015312 (Ifosfamide)

PDB for HMDB0015312 (Ifosfamide)

3D PDB for HMDB0015312 (Ifosfamide)

SMILES for HMDB0015312 (Ifosfamide)

INCHI for HMDB0015312 (Ifosfamide)

Structure for HMDB0015312 (Ifosfamide)

3D Structure for HMDB0015312 (Ifosfamide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra