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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:21:36 UTC

Update Date

2022-03-07 03:17:45 UTC

HMDB ID

HMDB0060449

Secondary Accession Numbers

HMDB60449

Metabolite Identification

Common Name

Carboxyphosphamide

Description

In contrast to previous adult studies on urinary metabolites, plasma carboxyphosphamide concentrations did not support the existence of polymorphic metabolism. Plasma concentrations of dechlorethylcyclophosphamide and carboxyphosphamide were correlated in individual patients, suggesting that the activity of both aldehyde dehydrogenase and cytochrome P450 enzyme(s) determine carboxyphosphamide production in vivo. (PMID: 7850793 ) Detoxification of cyclophosphamide is effected, in part, by hepatic class 1 aldehyde dehydrogenase (ALDH-1)-catalyzed oxidation of aldophosphamide, a pivotal aldehyde intermediate, to the nontoxic metabolite, carboxyphosphamide. (PMID: 9394035 ) A key finding was the detection of a metabolite, most likely carboxyphosphamide, that is formed only by cytosols from cells expressing either class 3 or class 1 ALDH. (PMID: 8662659 )

Structure

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

HMDB0060687
     RDKit          3D
Carboxycyclophosphamide
 31 30  0  0  0  0  0  0  0  0999 V2000
   -0.2136   -2.3973   -1.0831 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3156   -1.3750    0.3307 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.7658   -2.2497    1.4787 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424   -0.6843    0.7570 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0704   -0.6327   -0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3353    0.0050    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3817    0.0927   -0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1804   -0.3294   -1.9357 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6198    0.6474   -0.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5072   -0.1095    0.1294 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7213   -0.5100   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9153   -0.0501    0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4013   -0.7382   -0.3682 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9426    1.1420    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5373    2.1806    1.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4660    3.6358    0.8329 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0360   -1.8646   -1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543   -2.8728   -1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2847   -1.6208   -0.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759    0.0291   -1.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6623   -0.6250    1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1179    1.0111    0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7573    1.4533    0.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -1.6383   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8898   -0.2145   -1.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9372   -0.4572    1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591    1.0431    0.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8140    1.6196   -0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1462    1.0370    0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5171    2.5592    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858    1.9136    2.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  9 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  END


  Mrv0541 05161318212D          

 16 15  0  0  0  0            999 V2000
    2.2850    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3464   -1.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2617    0.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9184   -0.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4841    0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8570   -0.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6345    1.3089    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5752   -1.8616    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0869    1.3172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6896    0.3182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6578   -0.0782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6282   -1.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3094   -0.2845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9121    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1112    0.5163    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  1  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  2  0  0  0  0
 13  7  1  0  0  0  0
 15  6  1  0  0  0  0
 16 10  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060449

> <DATABASE_NAME>
hmdb

> <SMILES>
NP(=O)(OCCC(O)=O)N(CCCl)CCCl

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

> <INCHI_KEY>
QLAKAJLYYGOZQL-UHFFFAOYSA-N

> <FORMULA>
C7H15Cl2N2O4P

> <MOLECULAR_WEIGHT>
293.085

> <EXACT_MASS>
292.014648904

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.754625629019944

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.37

> <JCHEM_LOGP>
-0.3005671299999998

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.706220611681385

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.492940028774737

> <JCHEM_PKA_STRONGEST_BASIC>
-0.06859600490835949

> <JCHEM_POLAR_SURFACE_AREA>
92.86

> <JCHEM_REFRACTIVITY>
61.469

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carboxyphosphamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060687
     RDKit          3D
Carboxycyclophosphamide
 31 30  0  0  0  0  0  0  0  0999 V2000
   -0.2136   -2.3973   -1.0831 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3156   -1.3750    0.3307 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.7658   -2.2497    1.4787 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424   -0.6843    0.7570 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0704   -0.6327   -0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3353    0.0050    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3817    0.0927   -0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1804   -0.3294   -1.9357 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6198    0.6474   -0.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5072   -0.1095    0.1294 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7213   -0.5100   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9153   -0.0501    0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4013   -0.7382   -0.3682 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9426    1.1420    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5373    2.1806    1.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4660    3.6358    0.8329 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0360   -1.8646   -1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543   -2.8728   -1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2847   -1.6208   -0.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759    0.0291   -1.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6623   -0.6250    1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1179    1.0111    0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7573    1.4533    0.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -1.6383   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8898   -0.2145   -1.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9372   -0.4572    1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591    1.0431    0.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8140    1.6196   -0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1462    1.0370    0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5171    2.5592    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858    1.9136    2.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  9 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       4.265   0.594   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.647  -1.995   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.355   1.704   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.714  -0.886   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.770   0.224   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.333  -0.516   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0      -4.918   2.443   0.000  0.00  0.00          Cl+0
HETATM    9 Cl   UNK     0      -1.074  -3.475   0.000  0.00  0.00          Cl+0
HETATM   10  N   UNK     0      -0.162   2.459   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      -1.287   0.594   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       6.828  -0.146   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.906  -1.995   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.578  -0.531   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.703   1.334   0.000  0.00  0.00           O+0
HETATM   16  P   UNK     0       0.208   0.964   0.000  0.00  0.00           P+0
CONECT    1    6    7                                                       
CONECT    2    4    8                                                       
CONECT    3    5    9                                                       
CONECT    4    2   11                                                       
CONECT    5    3   11                                                       
CONECT    6    1   15                                                       
CONECT    7    1   12   13                                                  
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10   16                                                            
CONECT   11    4    5   16                                                  
CONECT   12    7                                                            
CONECT   13    7                                                            
CONECT   14   16                                                            
CONECT   15    6   16                                                       
CONECT   16   10   11   14   15                                             
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0060687
HETATM    1  N1  UNL     1      -0.214  -2.397  -1.083  1.00  0.00           N  
HETATM    2  P1  UNL     1      -0.316  -1.375   0.331  1.00  0.00           P  
HETATM    3  O1  UNL     1      -0.766  -2.250   1.479  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.142  -0.684   0.757  1.00  0.00           O  
HETATM    5  C1  UNL     1       2.070  -0.633  -0.257  1.00  0.00           C  
HETATM    6  C2  UNL     1       3.335   0.005   0.260  1.00  0.00           C  
HETATM    7  C3  UNL     1       4.382   0.093  -0.776  1.00  0.00           C  
HETATM    8  O3  UNL     1       4.180  -0.329  -1.936  1.00  0.00           O  
HETATM    9  O4  UNL     1       5.620   0.647  -0.490  1.00  0.00           O  
HETATM   10  N2  UNL     1      -1.507  -0.110   0.129  1.00  0.00           N  
HETATM   11  C4  UNL     1      -2.721  -0.510  -0.366  1.00  0.00           C  
HETATM   12  C5  UNL     1      -3.915  -0.050   0.422  1.00  0.00           C  
HETATM   13 CL1  UNL     1      -5.401  -0.738  -0.368  1.00  0.00          CL  
HETATM   14  C6  UNL     1      -0.943   1.142   0.150  1.00  0.00           C  
HETATM   15  C7  UNL     1      -1.537   2.181   1.038  1.00  0.00           C  
HETATM   16 CL2  UNL     1      -0.466   3.636   0.833  1.00  0.00          CL  
HETATM   17  H1  UNL     1       0.036  -1.865  -1.943  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.154  -2.873  -1.159  1.00  0.00           H  
HETATM   19  H3  UNL     1       2.285  -1.621  -0.708  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.676   0.029  -1.049  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.662  -0.625   1.131  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.118   1.011   0.652  1.00  0.00           H  
HETATM   23  H7  UNL     1       5.757   1.453   0.101  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.767  -1.638  -0.395  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.890  -0.215  -1.467  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.937  -0.457   1.448  1.00  0.00           H  
HETATM   27  H11 UNL     1      -4.059   1.043   0.426  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.814   1.620  -0.873  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.146   1.037   0.499  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.517   2.559   0.706  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.486   1.914   2.103  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3    3    4   10
CONECT    4    5
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8    8    9
CONECT    9   23
CONECT   10   11   14
CONECT   11   12   24   25
CONECT   12   13   26   27
CONECT   14   15   28   29
CONECT   15   16   30   31
END

HMDB0060687
     RDKit          3D
Carboxycyclophosphamide
 31 30  0  0  0  0  0  0  0  0999 V2000
   -0.2136   -2.3973   -1.0831 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3156   -1.3750    0.3307 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.7658   -2.2497    1.4787 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424   -0.6843    0.7570 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0704   -0.6327   -0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3353    0.0050    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3817    0.0927   -0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1804   -0.3294   -1.9357 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6198    0.6474   -0.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5072   -0.1095    0.1294 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7213   -0.5100   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9153   -0.0501    0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4013   -0.7382   -0.3682 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9426    1.1420    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5373    2.1806    1.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4660    3.6358    0.8329 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0360   -1.8646   -1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543   -2.8728   -1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2847   -1.6208   -0.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759    0.0291   -1.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6623   -0.6250    1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1179    1.0111    0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7573    1.4533    0.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -1.6383   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8898   -0.2145   -1.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9372   -0.4572    1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591    1.0431    0.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8140    1.6196   -0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1462    1.0370    0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5171    2.5592    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858    1.9136    2.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  9 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 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
Carboxycyclophosphamide	Kegg
Carboxyphosphamide, (S)-isomer	HMDB
Carboxyphosphamide, (R)-isomer	HMDB

Chemical Formula

C₇H₁₅Cl₂N₂O₄P

Average Molecular Weight

293.085

Monoisotopic Molecular Weight

292.014648904

IUPAC Name

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

Traditional Name

carboxyphosphamide

CAS Registry Number

Not Available

SMILES

NP(=O)(OCCC(O)=O)N(CCCl)CCCl

InChI Identifier

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

InChI Key

QLAKAJLYYGOZQL-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
Phosphoric acid ester
Organic phosphoric acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organopnictogen compound
Alkyl chloride
Organooxygen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Carbonyl group
Alkyl halide
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

nitrogen mustard (CHEBI:3410 )

Ontology

Not Available

Exogenous (HMDB: HMDB0060449)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Cyclophosphamide Action Pathway (PathBank: SMP0000447)

Metabolic pathway

Cyclophosphamide Metabolism Pathway (PathBank: SMP0000604)

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	13.6 g/L	ALOGPS
logP	0.37	ALOGPS
logP	-0.3	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-0.069	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.86 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	61.47 m³·mol⁻¹	ChemAxon
Polarizability	25.75 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]+	154.401	30932474
DeepCCS	[M-H]-	152.043	30932474
DeepCCS	[M-2H]-	186.08	30932474
DeepCCS	[M+Na]+	160.83	30932474
AllCCS	[M+H]+	158.0	32859911
AllCCS	[M+H-H2O]+	155.1	32859911
AllCCS	[M+NH4]+	160.7	32859911
AllCCS	[M+Na]+	161.4	32859911
AllCCS	[M-H]-	156.2	32859911
AllCCS	[M+Na-2H]-	157.3	32859911
AllCCS	[M+HCOO]-	158.7	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.	3.54 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0878 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.27 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carboxyphosphamide	NP(=O)(OCCC(O)=O)N(CCCl)CCCl	3170.5	Standard polar	33892256
Carboxyphosphamide	NP(=O)(OCCC(O)=O)N(CCCl)CCCl	2022.3	Standard non polar	33892256
Carboxyphosphamide	NP(=O)(OCCC(O)=O)N(CCCl)CCCl	2183.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carboxyphosphamide,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCOP(N)(=O)N(CCCl)CCCl	2254.1	Semi standard non polar	33892256
Carboxyphosphamide,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCOP(N)(=O)N(CCCl)CCCl	2254.1	Semi standard non polar	33892256
Carboxyphosphamide,1TMS,isomer #2	C[Si](C)(C)NP(=O)(OCCC(=O)O)N(CCCl)CCCl	2286.6	Semi standard non polar	33892256
Carboxyphosphamide,1TMS,isomer #2	C[Si](C)(C)NP(=O)(OCCC(=O)O)N(CCCl)CCCl	2286.6	Semi standard non polar	33892256
Carboxyphosphamide,2TMS,isomer #1	C[Si](C)(C)NP(=O)(OCCC(=O)O[Si](C)(C)C)N(CCCl)CCCl	2264.9	Semi standard non polar	33892256
Carboxyphosphamide,2TMS,isomer #1	C[Si](C)(C)NP(=O)(OCCC(=O)O[Si](C)(C)C)N(CCCl)CCCl	2223.7	Standard non polar	33892256
Carboxyphosphamide,2TMS,isomer #1	C[Si](C)(C)NP(=O)(OCCC(=O)O[Si](C)(C)C)N(CCCl)CCCl	2881.3	Standard polar	33892256
Carboxyphosphamide,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCC(=O)O)N(CCCl)CCCl	2394.4	Semi standard non polar	33892256
Carboxyphosphamide,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCC(=O)O)N(CCCl)CCCl	2283.7	Standard non polar	33892256
Carboxyphosphamide,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCC(=O)O)N(CCCl)CCCl	2974.6	Standard polar	33892256
Carboxyphosphamide,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C	2382.7	Semi standard non polar	33892256
Carboxyphosphamide,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C	2367.0	Standard non polar	33892256
Carboxyphosphamide,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C	2688.2	Standard polar	33892256
Carboxyphosphamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCOP(N)(=O)N(CCCl)CCCl	2492.2	Semi standard non polar	33892256
Carboxyphosphamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCOP(N)(=O)N(CCCl)CCCl	2492.2	Semi standard non polar	33892256
Carboxyphosphamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NP(=O)(OCCC(=O)O)N(CCCl)CCCl	2549.9	Semi standard non polar	33892256
Carboxyphosphamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NP(=O)(OCCC(=O)O)N(CCCl)CCCl	2549.9	Semi standard non polar	33892256
Carboxyphosphamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NP(=O)(OCCC(=O)O[Si](C)(C)C(C)(C)C)N(CCCl)CCCl	2726.8	Semi standard non polar	33892256
Carboxyphosphamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NP(=O)(OCCC(=O)O[Si](C)(C)C(C)(C)C)N(CCCl)CCCl	2633.5	Standard non polar	33892256
Carboxyphosphamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NP(=O)(OCCC(=O)O[Si](C)(C)C(C)(C)C)N(CCCl)CCCl	3015.3	Standard polar	33892256
Carboxyphosphamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCC(=O)O)N(CCCl)CCCl	2843.7	Semi standard non polar	33892256
Carboxyphosphamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCC(=O)O)N(CCCl)CCCl	2645.9	Standard non polar	33892256
Carboxyphosphamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCC(=O)O)N(CCCl)CCCl	3039.2	Standard polar	33892256
Carboxyphosphamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3046.1	Semi standard non polar	33892256
Carboxyphosphamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2868.2	Standard non polar	33892256
Carboxyphosphamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2883.6	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Not Available

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

C07646

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carboxycyclophosphamide

METLIN ID

Not Available

PubChem Compound

31515

PDB ID

Not Available

ChEBI ID

3410

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
Dockham PA, Sreerama L, Sladek NE: Relative contribution of human erythrocyte aldehyde dehydrogenase to the systemic detoxification of the oxazaphosphorines. Drug Metab Dispos. 1997 Dec;25(12):1436-41. [PubMed:9394035 ]
Yule SM, Boddy AV, Cole M, Price L, Wyllie R, Tasso MJ, Pearson AD, Idle JR: Cyclophosphamide metabolism in children. Cancer Res. 1995 Feb 15;55(4):803-9. [PubMed:7850793 ]
Bunting KD, Townsend AJ: Protection by transfected rat or human class 3 aldehyde dehydrogenase against the cytotoxic effects of oxazaphosphorine alkylating agents in hamster V79 cell lines. Demonstration of aldophosphamide metabolism by the human cytosolic class 3 isozyme. J Biol Chem. 1996 May 17;271(20):11891-6. [PubMed:8662659 ]

Enzymes

Enzyme Details

1. Aldehyde dehydrogenase, dimeric NADP-preferring

General function:: Involved in oxidoreductase activity
Specific function:: ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:: ALDH3A1
Uniprot ID:: P30838
Molecular weight:: 50394.57

Reactions

Aldophosphamide + NAD + Water → Carboxyphosphamide + NADH + Hydrogen Ion	details
Aldophosphamide + NADP + Water → Carboxyphosphamide + NADPH + Hydrogen Ion	details

Enzyme Details

2. Aldehyde dehydrogenase family 1 member A3

General function:: Involved in oxidoreductase activity
Specific function:: Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:: ALDH1A3
Uniprot ID:: P47895
Molecular weight:: 56107.995

Reactions

Aldophosphamide + NAD + Water → Carboxyphosphamide + NADH + Hydrogen Ion	details
Aldophosphamide + NADP + Water → Carboxyphosphamide + NADPH + Hydrogen Ion	details

Enzyme Details

3. Aldehyde dehydrogenase family 3 member B2

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ALDH3B2
Uniprot ID:: P48448
Molecular weight:: 42623.62

Reactions

Aldophosphamide + NAD + Water → Carboxyphosphamide + NADH + Hydrogen Ion	details
Aldophosphamide + NADP + Water → Carboxyphosphamide + NADPH + Hydrogen Ion	details

Enzyme Details

4. Aldehyde dehydrogenase family 3 member B1

General function:: Involved in oxidoreductase activity
Specific function:: Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:: ALDH3B1
Uniprot ID:: P43353
Molecular weight:: 51839.245

Reactions

Aldophosphamide + NAD + Water → Carboxyphosphamide + NADH + Hydrogen Ion	details
Aldophosphamide + NADP + Water → Carboxyphosphamide + NADPH + Hydrogen Ion	details

Showing metabocard for Carboxyphosphamide (HMDB0060449)

MOL for HMDB0060449 (Carboxyphosphamide)

3D MOL for HMDB0060449 (Carboxyphosphamide)

3D SDF for HMDB0060449 (Carboxyphosphamide)

3D-SDF for HMDB0060449 (Carboxyphosphamide)

PDB for HMDB0060449 (Carboxyphosphamide)

3D PDB for HMDB0060449 (Carboxyphosphamide)

SMILES for HMDB0060449 (Carboxyphosphamide)

INCHI for HMDB0060449 (Carboxyphosphamide)

Structure for HMDB0060449 (Carboxyphosphamide)

3D Structure for HMDB0060449 (Carboxyphosphamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

Reactions

Reactions