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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 19:13:56 UTC

Update Date

2019-07-23 07:14:52 UTC

HMDB ID

HMDB0060692

Secondary Accession Numbers

HMDB60692

Metabolite Identification

Common Name

Carboxyifosfamide

Description

Carboxyifosfamide belongs to the class of organic compounds known as phosphoric monoester diamides. These are organophosphorus compounds containing a monoamide derivative of a phosphoric acid diester functional group. They have the general structure R1OP(=O)(N(R2)R3)N(R4)R5, where R1 = organyl group and R2-R5 = H or organyl. Carboxyifosfamide is an extremely weak basic (essentially neutral) compound (based on its pKa). carboxyifosfamide can be biosynthesized from aldoifosfamide through the action of the enzyme retinal dehydrogenase 1. In humans, carboxyifosfamide is involved in ifosfamide metabolism pathway. Carboxyifosfamide is a metabolite of ifosfamide. Ifosfamide (also marketed as Mitoxana and Ifex) is a nitrogen mustard alkylating agent used in the treatment of cancer. It is sometimes abbreviated 'IFO'.

Structure

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

HMDB0060692
     RDKit          3D
Carboxyifosfamide
 31 30  0  0  0  0  0  0  0  0999 V2000
    4.6753    0.5737    1.1004 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3109   -0.1369    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9475   -0.0799   -1.0957 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1593   -1.0498    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8996   -0.1823    0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8163   -0.9872    0.6225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438   -0.0406    0.6922 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.9269    0.0126    2.2298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3337    1.5948    0.2099 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6457    2.1090   -0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6250    3.5847   -0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2815    4.0139   -0.9771 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192   -0.8151   -0.1217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799   -2.1170   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5484   -3.1190   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1310   -2.6901   -0.6953 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6145    0.3822   -1.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3072   -1.4843    1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678   -1.8701   -0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931    0.4317   -0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9043    0.5397    1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005    2.1754    1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199    1.8693    0.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    1.5961   -1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9078    3.8378   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4293    4.2079    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483   -0.4724   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5678   -2.1767   -1.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5105   -2.4462   -0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4711   -3.1519    1.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2322   -4.1093   -0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  9 22  1  0
 10 23  1  0
 10 24  1  0
 11 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

 
  Mrv0541 06181312132D          
 
 16 15  0  0  0  0            999 V2000
   14.9919  -10.5134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9953  -11.3401    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.2788  -10.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2857  -11.7638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7222  -11.7397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2788  -10.9267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5657  -10.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2994  -12.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8562  -10.1000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.0194  -12.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4119  -11.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1369  -11.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8570  -11.2844    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.0304  -13.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7505  -14.1991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3240  -14.2174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060692

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCOP(=O)(NCCCl)NCCCl

> <INCHI_IDENTIFIER>
InChI=1S/C7H15Cl2N2O4P/c8-2-4-10-16(14,11-5-3-9)15-6-1-7(12)13/h1-6H2,(H,12,13)(H2,10,11,14)

> <INCHI_KEY>
DNDBVHDNSYHKLI-UHFFFAOYSA-N

> <FORMULA>
C7H15Cl2N2O4P

> <MOLECULAR_WEIGHT>
293.085

> <EXACT_MASS>
292.014648904

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.099741096054235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-({bis[(2-chloroethyl)amino]phosphoryl}oxy)propanoic acid

> <ALOGPS_LOGP>
-1.45

> <JCHEM_LOGP>
-0.3005671299999998

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.28418500353013

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.492941502689043

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3186206150444226

> <JCHEM_POLAR_SURFACE_AREA>
87.66

> <JCHEM_REFRACTIVITY>
61.46900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carboxyifosfamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060692
     RDKit          3D
Carboxyifosfamide
 31 30  0  0  0  0  0  0  0  0999 V2000
    4.6753    0.5737    1.1004 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3109   -0.1369    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9475   -0.0799   -1.0957 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1593   -1.0498    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8996   -0.1823    0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8163   -0.9872    0.6225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438   -0.0406    0.6922 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.9269    0.0126    2.2298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3337    1.5948    0.2099 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6457    2.1090   -0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6250    3.5847   -0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2815    4.0139   -0.9771 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192   -0.8151   -0.1217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799   -2.1170   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5484   -3.1190   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1310   -2.6901   -0.6953 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6145    0.3822   -1.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3072   -1.4843    1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678   -1.8701   -0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931    0.4317   -0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9043    0.5397    1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005    2.1754    1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199    1.8693    0.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    1.5961   -1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9078    3.8378   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4293    4.2079    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483   -0.4724   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5678   -2.1767   -1.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5105   -2.4462   -0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4711   -3.1519    1.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2322   -4.1093   -0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  9 22  1  0
 10 23  1  0
 10 24  1  0
 11 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                                 18-JUN-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-JUN-13         0                                  
HETATM    1  N   UNK     0      27.985 -19.625   0.000  0.00  0.00           N+0
HETATM    2  P   UNK     0      27.991 -21.168   0.000  0.00  0.00           P+0
HETATM    3  C   UNK     0      26.654 -18.853   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      26.667 -21.959   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      29.348 -21.914   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0      26.654 -20.397   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      25.323 -19.625   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.692 -23.496   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0      23.998 -18.853   0.000  0.00  0.00          Cl+0
HETATM   10  C   UNK     0      28.036 -24.248   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.636 -21.134   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.989 -21.878   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      33.333 -21.064   0.000  0.00  0.00          Cl+0
HETATM   14  C   UNK     0      28.057 -25.753   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      29.401 -26.505   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      26.738 -26.539   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5    6                                             
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    2   11                                                       
CONECT    6    2                                                            
CONECT    7    3    9                                                       
CONECT    8    4   10                                                       
CONECT    9    7                                                            
CONECT   10    8   14                                                       
CONECT   11    5   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0060692
HETATM    1  O1  UNL     1       4.675   0.574   1.100  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.311  -0.137   0.117  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.948  -0.080  -1.096  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.159  -1.050   0.381  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.900  -0.182   0.451  1.00  0.00           C  
HETATM    6  O3  UNL     1       0.816  -0.987   0.623  1.00  0.00           O  
HETATM    7  P1  UNL     1      -0.544  -0.041   0.692  1.00  0.00           P  
HETATM    8  O4  UNL     1      -0.927   0.013   2.230  1.00  0.00           O  
HETATM    9  N1  UNL     1      -0.334   1.595   0.210  1.00  0.00           N  
HETATM   10  C4  UNL     1      -1.646   2.109  -0.180  1.00  0.00           C  
HETATM   11  C5  UNL     1      -1.625   3.585  -0.485  1.00  0.00           C  
HETATM   12 CL1  UNL     1      -3.282   4.014  -0.977  1.00  0.00          CL  
HETATM   13  N2  UNL     1      -1.819  -0.815  -0.122  1.00  0.00           N  
HETATM   14  C6  UNL     1      -1.480  -2.117  -0.587  1.00  0.00           C  
HETATM   15  C7  UNL     1      -2.548  -3.119  -0.127  1.00  0.00           C  
HETATM   16 CL2  UNL     1      -4.131  -2.690  -0.695  1.00  0.00          CL  
HETATM   17  H1  UNL     1       4.615   0.382  -1.924  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.307  -1.484   1.421  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.068  -1.870  -0.362  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.793   0.432  -0.492  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.904   0.540   1.285  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.001   2.175   1.053  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.420   1.869   0.556  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.874   1.596  -1.153  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.908   3.838  -1.269  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.429   4.208   0.431  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.748  -0.472  -0.124  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.568  -2.177  -1.722  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.510  -2.446  -0.316  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.471  -3.152   1.017  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.232  -4.109  -0.463  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7
CONECT    7    8    8    9   13
CONECT    9   10   22
CONECT   10   11   23   24
CONECT   11   12   25   26
CONECT   13   14   27
CONECT   14   15   28   29
CONECT   15   16   30   31
END

HMDB0060692
     RDKit          3D
Carboxyifosfamide
 31 30  0  0  0  0  0  0  0  0999 V2000
    4.6753    0.5737    1.1004 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3109   -0.1369    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9475   -0.0799   -1.0957 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1593   -1.0498    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8996   -0.1823    0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8163   -0.9872    0.6225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438   -0.0406    0.6922 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.9269    0.0126    2.2298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3337    1.5948    0.2099 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6457    2.1090   -0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6250    3.5847   -0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2815    4.0139   -0.9771 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192   -0.8151   -0.1217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799   -2.1170   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5484   -3.1190   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1310   -2.6901   -0.6953 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6145    0.3822   -1.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3072   -1.4843    1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678   -1.8701   -0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931    0.4317   -0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9043    0.5397    1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005    2.1754    1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199    1.8693    0.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    1.5961   -1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9078    3.8378   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4293    4.2079    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483   -0.4724   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5678   -2.1767   -1.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5105   -2.4462   -0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4711   -3.1519    1.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2322   -4.1093   -0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  9 22  1  0
 10 23  1  0
 10 24  1  0
 11 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
3-({Bis[(2-chloroethyl)amino]phosphoryl}oxy)propanoic acid	HMDB
3-({Bis[(2-chloroethyl)amino]phosphoryl}oxy)propanoate	HMDB

Chemical Formula

C₇H₁₅Cl₂N₂O₄P

Average Molecular Weight

293.085

Monoisotopic Molecular Weight

292.014648904

IUPAC Name

3-({bis[(2-chloroethyl)amino]phosphoryl}oxy)propanoic acid

Traditional Name

carboxyifosfamide

CAS Registry Number

Not Available

SMILES

OC(=O)CCOP(=O)(NCCCl)NCCCl

InChI Identifier

InChI=1S/C7H15Cl2N2O4P/c8-2-4-10-16(14,11-5-3-9)15-6-1-7(12)13/h1-6H2,(H,12,13)(H2,10,11,14)

InChI Key

DNDBVHDNSYHKLI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphoric monoester diamides. These are organophosphorus compounds containing a monoamide derivative of a phosphoric acid diester functional group. They have the general structure R1OP(=O)(N(R2)R3)N(R4)R5, where R1 = organyl group and R2-R5 = H or organyl.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Organic phosphoramides

Direct Parent

Phosphoric monoester diamides

Alternative Parents

Substituents

Phosphoric monoester diamide
Phosphoric acid ester
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Alkyl halide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphorodiamide (CHEBI:80564 )

Ontology

Not Available

Liver (HMDB: HMDB0060692)
Kidney (HMDB: HMDB0060692)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060692)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060692)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Ifosfamide Action Pathway (PathBank: SMP0000448)

Metabolic pathway

Ifosfamide Metabolism Pathway (PathBank: SMP0000605)

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
Water Solubility	3.76 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-0.3	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	87.66 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	61.47 m³·mol⁻¹	ChemAxon
Polarizability	26.1 Å³	ChemAxon
Number of Rings	0	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]+	155.432	30932474
DeepCCS	[M-H]-	153.074	30932474
DeepCCS	[M-2H]-	187.578	30932474
DeepCCS	[M+Na]+	162.238	30932474
AllCCS	[M+H]+	158.7	32859911
AllCCS	[M+H-H2O]+	155.8	32859911
AllCCS	[M+NH4]+	161.4	32859911
AllCCS	[M+Na]+	162.1	32859911
AllCCS	[M-H]-	156.0	32859911
AllCCS	[M+Na-2H]-	157.2	32859911
AllCCS	[M+HCOO]-	158.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carboxyifosfamide	OC(=O)CCOP(=O)(NCCCl)NCCCl	3475.7	Standard polar	33892256
Carboxyifosfamide	OC(=O)CCOP(=O)(NCCCl)NCCCl	2026.5	Standard non polar	33892256
Carboxyifosfamide	OC(=O)CCOP(=O)(NCCCl)NCCCl	2228.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carboxyifosfamide,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)NCCCl	2260.5	Semi standard non polar	33892256
Carboxyifosfamide,1TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC(=O)O	2304.2	Semi standard non polar	33892256
Carboxyifosfamide,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C	2276.0	Semi standard non polar	33892256
Carboxyifosfamide,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C	2195.7	Standard non polar	33892256
Carboxyifosfamide,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C	2946.9	Standard polar	33892256
Carboxyifosfamide,2TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(OCCC(=O)O)N(CCCl)[Si](C)(C)C	2357.4	Semi standard non polar	33892256
Carboxyifosfamide,2TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(OCCC(=O)O)N(CCCl)[Si](C)(C)C	2213.9	Standard non polar	33892256
Carboxyifosfamide,2TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(OCCC(=O)O)N(CCCl)[Si](C)(C)C	2899.4	Standard polar	33892256
Carboxyifosfamide,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C	2351.8	Semi standard non polar	33892256
Carboxyifosfamide,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C	2278.5	Standard non polar	33892256
Carboxyifosfamide,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C	2651.5	Standard polar	33892256
Carboxyifosfamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)NCCCl	2517.8	Semi standard non polar	33892256
Carboxyifosfamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC(=O)O	2552.8	Semi standard non polar	33892256
Carboxyifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C	2754.2	Semi standard non polar	33892256
Carboxyifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C	2614.7	Standard non polar	33892256
Carboxyifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C	3041.3	Standard polar	33892256
Carboxyifosfamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCC(=O)O)N(CCCl)[Si](C)(C)C(C)(C)C	2820.5	Semi standard non polar	33892256
Carboxyifosfamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCC(=O)O)N(CCCl)[Si](C)(C)C(C)(C)C	2570.9	Standard non polar	33892256
Carboxyifosfamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCC(=O)O)N(CCCl)[Si](C)(C)C(C)(C)C	3036.6	Standard polar	33892256
Carboxyifosfamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C	3018.5	Semi standard non polar	33892256
Carboxyifosfamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C	2766.0	Standard non polar	33892256
Carboxyifosfamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C	2902.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Carboxyifosfamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-05tf-1890000000-2eff8b9169eef6666cd3	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carboxyifosfamide GC-MS (1 TMS) - 70eV, Positive	splash10-00di-5391000000-d216d7335b85567daad5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carboxyifosfamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carboxyifosfamide 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 - Carboxyifosfamide 10V, Positive-QTOF	splash10-004i-4090000000-ed86043bb226a0a90c73	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxyifosfamide 20V, Positive-QTOF	splash10-0089-9000000000-04cd05b425913ba7aabd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxyifosfamide 40V, Positive-QTOF	splash10-01t9-9000000000-0e5440da361aec660c7f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxyifosfamide 10V, Negative-QTOF	splash10-002f-2090000000-4f81c39a66666414545e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxyifosfamide 20V, Negative-QTOF	splash10-0ik9-9450000000-bfe03fb15784b1311ec5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxyifosfamide 40V, Negative-QTOF	splash10-004i-9100000000-ddd742ec6e60562672f9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxyifosfamide 10V, Negative-QTOF	splash10-0006-0090000000-16bff749b532fb94032d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxyifosfamide 20V, Negative-QTOF	splash10-015i-0940000000-ce35c5ce8b6fb3d9148e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxyifosfamide 40V, Negative-QTOF	splash10-000l-0900000000-dbed6c8ef07e81daea31	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxyifosfamide 10V, Positive-QTOF	splash10-0006-0090000000-87d1d71c5b58ac18a93b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxyifosfamide 20V, Positive-QTOF	splash10-0ac0-3960000000-6d053255e23c8e96819c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxyifosfamide 40V, Positive-QTOF	splash10-0a4i-5900000000-bf79be778247d8d705b5	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)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

C16557

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124143

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Carboxyifosfamide (HMDB0060692)

MOL for HMDB0060692 (Carboxyifosfamide)

3D MOL for HMDB0060692 (Carboxyifosfamide)

3D SDF for HMDB0060692 (Carboxyifosfamide)

3D-SDF for HMDB0060692 (Carboxyifosfamide)

PDB for HMDB0060692 (Carboxyifosfamide)

3D PDB for HMDB0060692 (Carboxyifosfamide)

SMILES for HMDB0060692 (Carboxyifosfamide)

INCHI for HMDB0060692 (Carboxyifosfamide)

Structure for HMDB0060692 (Carboxyifosfamide)

3D Structure for HMDB0060692 (Carboxyifosfamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra