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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 17:14:02 UTC

Update Date

2019-07-23 07:14:39 UTC

HMDB ID

HMDB0060588

Secondary Accession Numbers

HMDB60588

Metabolite Identification

Common Name

Aldoifosfamide

Description

Aldoifosfamide 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. Aldoifosfamide is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, aldoifosfamide is involved in ifosfamide metabolism pathway. Ifosfamide (pronounced eye. fos'. fa. mide) (also marketed as Mitoxana and Ifex) is a nitrogen mustard alkylating agent used in the treatment of cancer. Aldoifosfamide is a metabolite of ifosfamide. It is sometimes abbreviated 'IFO''.

Structure

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

HMDB0060588
     RDKit          3D
Aldoifosfamide
 30 29  0  0  0  0  0  0  0  0999 V2000
    5.5846   -1.0524    0.5878 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798   -1.0006    0.6744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5348   -0.9897   -0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0720   -0.9219   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8066    0.2363    0.5433 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1708    0.2989    0.9420 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.0628   -0.1269    2.4063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5168    1.8628    0.7893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2503    2.0747   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8379    3.4647   -0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7347    3.6688   -2.0346 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6822   -0.8835    0.0025 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8276   -1.3540    0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6154   -2.3913   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2005   -1.6912   -1.5451 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9271   -0.9624    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7379   -1.9320   -1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8334   -0.1558   -1.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8332   -1.8476    0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4976   -0.8537   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9325    2.2669    1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6311    1.8226   -1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193    1.3669   -0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139    3.7030    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332    4.2403   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9723   -0.5482   -0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5343   -0.5301    0.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5219   -1.8202    1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0043   -3.2911   -0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5124   -2.6534    0.5752 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
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 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
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
M  END


  Mrv0541 06151310092D          

 15 14  0  0  0  0            999 V2000
    1.1270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  1  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 14  7  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060588

> <DATABASE_NAME>
hmdb

> <SMILES>
ClCCNP(=O)(NCCCl)OCCC=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H15Cl2N2O3P/c8-2-4-10-15(13,11-5-3-9)14-7-1-6-12/h6H,1-5,7H2,(H2,10,11,13)

> <INCHI_KEY>
IPTJZZUYNOWWHM-UHFFFAOYSA-N

> <FORMULA>
C7H15Cl2N2O3P

> <MOLECULAR_WEIGHT>
277.085

> <EXACT_MASS>
276.019734282

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.141984306870135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.23

> <JCHEM_LOGP>
-0.45918338233333306

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.261213684743769

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.241903110951657

> <JCHEM_PKA_STRONGEST_BASIC>
-2.318603221086421

> <JCHEM_POLAR_SURFACE_AREA>
67.42999999999999

> <JCHEM_REFRACTIVITY>
60.5436

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aldoifosfamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060588
     RDKit          3D
Aldoifosfamide
 30 29  0  0  0  0  0  0  0  0999 V2000
    5.5846   -1.0524    0.5878 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798   -1.0006    0.6744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5348   -0.9897   -0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0720   -0.9219   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8066    0.2363    0.5433 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1708    0.2989    0.9420 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.0628   -0.1269    2.4063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5168    1.8628    0.7893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2503    2.0747   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8379    3.4647   -0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7347    3.6688   -2.0346 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6822   -0.8835    0.0025 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8276   -1.3540    0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6154   -2.3913   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2005   -1.6912   -1.5451 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9271   -0.9624    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7379   -1.9320   -1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8334   -0.1558   -1.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8332   -1.8476    0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4976   -0.8537   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9325    2.2669    1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6311    1.8226   -1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193    1.3669   -0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139    3.7030    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332    4.2403   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9723   -0.5482   -0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5343   -0.5301    0.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5219   -1.8202    1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0043   -3.2911   -0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5124   -2.6534    0.5752 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
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 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
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0       2.104   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.875   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.874   6.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       8.208   0.770   0.000  0.00  0.00          Cl+0
HETATM    9 Cl   UNK     0      -2.461   0.770   0.000  0.00  0.00          Cl+0
HETATM   10  N   UNK     0       4.207   1.540   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       1.540   0.000   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       2.104   7.438   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.644  -0.564   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   15  P   UNK     0       2.874   0.770   0.000  0.00  0.00           P+0
CONECT    1    6    7                                                       
CONECT    2    4    8                                                       
CONECT    3    5    9                                                       
CONECT    4    2   10                                                       
CONECT    5    3   11                                                       
CONECT    6    1   12                                                       
CONECT    7    1   14                                                       
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4   15                                                       
CONECT   11    5   15                                                       
CONECT   12    6                                                            
CONECT   13   15                                                            
CONECT   14    7   15                                                       
CONECT   15   10   11   13   14                                             
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0060588
HETATM    1  O1  UNL     1       5.585  -1.052   0.588  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.380  -1.001   0.674  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.535  -0.990  -0.549  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.072  -0.922  -0.185  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.807   0.236   0.543  1.00  0.00           O  
HETATM    6  P1  UNL     1       0.171   0.299   0.942  1.00  0.00           P  
HETATM    7  O3  UNL     1       0.063  -0.127   2.406  1.00  0.00           O  
HETATM    8  N1  UNL     1      -0.517   1.863   0.789  1.00  0.00           N  
HETATM    9  C4  UNL     1      -1.250   2.075  -0.422  1.00  0.00           C  
HETATM   10  C5  UNL     1      -1.838   3.465  -0.514  1.00  0.00           C  
HETATM   11 CL1  UNL     1      -2.735   3.669  -2.035  1.00  0.00          CL  
HETATM   12  N2  UNL     1      -0.682  -0.883   0.002  1.00  0.00           N  
HETATM   13  C6  UNL     1      -1.828  -1.354   0.750  1.00  0.00           C  
HETATM   14  C7  UNL     1      -2.615  -2.391  -0.019  1.00  0.00           C  
HETATM   15 CL2  UNL     1      -3.200  -1.691  -1.545  1.00  0.00          CL  
HETATM   16  H1  UNL     1       3.927  -0.962   1.654  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.738  -1.932  -1.087  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.833  -0.156  -1.221  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.833  -1.848   0.386  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.498  -0.854  -1.131  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.932   2.267   1.629  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.631   1.823  -1.296  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.119   1.367  -0.433  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.514   3.703   0.304  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.033   4.240  -0.511  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.972  -0.548  -0.927  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.534  -0.530   0.982  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.522  -1.820   1.702  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.004  -3.291  -0.196  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.512  -2.653   0.575  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6
CONECT    6    7    7    8   12
CONECT    8    9   21
CONECT    9   10   22   23
CONECT   10   11   24   25
CONECT   12   13   26
CONECT   13   14   27   28
CONECT   14   15   29   30
END

HMDB0060588
     RDKit          3D
Aldoifosfamide
 30 29  0  0  0  0  0  0  0  0999 V2000
    5.5846   -1.0524    0.5878 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798   -1.0006    0.6744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5348   -0.9897   -0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0720   -0.9219   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8066    0.2363    0.5433 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1708    0.2989    0.9420 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.0628   -0.1269    2.4063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5168    1.8628    0.7893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2503    2.0747   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8379    3.4647   -0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7347    3.6688   -2.0346 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6822   -0.8835    0.0025 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8276   -1.3540    0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6154   -2.3913   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2005   -1.6912   -1.5451 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9271   -0.9624    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7379   -1.9320   -1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8334   -0.1558   -1.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8332   -1.8476    0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4976   -0.8537   -1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9325    2.2669    1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6311    1.8226   -1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193    1.3669   -0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139    3.7030    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332    4.2403   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9723   -0.5482   -0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5343   -0.5301    0.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5219   -1.8202    1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0043   -3.2911   -0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5124   -2.6534    0.5752 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
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 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
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₇H₁₅Cl₂N₂O₃P

Average Molecular Weight

277.085

Monoisotopic Molecular Weight

276.019734282

IUPAC Name

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

Traditional Name

aldoifosfamide

CAS Registry Number

Not Available

SMILES

ClCCNP(=O)(NCCCl)OCCC=O

InChI Identifier

InChI=1S/C7H15Cl2N2O3P/c8-2-4-10-15(13,11-5-3-9)14-7-1-6-12/h6H,1-5,7H2,(H2,10,11,13)

InChI Key

IPTJZZUYNOWWHM-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
Alpha-hydrogen aldehyde
Aldehyde
Organic oxide
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Organic nitrogen compound
Alkyl halide
Alkyl chloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphorodiamide (CHEBI:80563 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060588)

Organ

Kidney (HMDB: HMDB0060588)
Liver (HMDB: HMDB0060588)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060588)

Cellular substructure

Cytoplasm (HMDB: HMDB0060588)

Source

Endogenous

Endogenous (HMDB: HMDB0060588)

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	3.58 g/L	ALOGPS
logP	0.23	ALOGPS
logP	-0.46	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.43 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	60.54 m³·mol⁻¹	ChemAxon
Polarizability	25.14 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	153.184	30932474
DeepCCS	[M-H]-	149.396	30932474
DeepCCS	[M-2H]-	186.329	30932474
DeepCCS	[M+Na]+	162.018	30932474
AllCCS	[M+H]+	155.8	32859911
AllCCS	[M+H-H2O]+	152.8	32859911
AllCCS	[M+NH4]+	158.5	32859911
AllCCS	[M+Na]+	159.3	32859911
AllCCS	[M-H]-	154.1	32859911
AllCCS	[M+Na-2H]-	155.4	32859911
AllCCS	[M+HCOO]-	157.0	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.	5.07 minutes	32390414
Predicted by Siyang on May 30, 2022	12.2073 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.26 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1212.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	321.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	132.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	88.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	412.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	559.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	66.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	915.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	385.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1345.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	318.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	328.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	318.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	238.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	26.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aldoifosfamide	ClCCNP(=O)(NCCCl)OCCC=O	2849.3	Standard polar	33892256
Aldoifosfamide	ClCCNP(=O)(NCCCl)OCCC=O	1823.3	Standard non polar	33892256
Aldoifosfamide	ClCCNP(=O)(NCCCl)OCCC=O	2005.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aldoifosfamide,1TMS,isomer #1	C[Si](C)(C)OC=CCOP(=O)(NCCCl)NCCCl	2264.8	Semi standard non polar	33892256
Aldoifosfamide,1TMS,isomer #1	C[Si](C)(C)OC=CCOP(=O)(NCCCl)NCCCl	2013.6	Standard non polar	33892256
Aldoifosfamide,1TMS,isomer #1	C[Si](C)(C)OC=CCOP(=O)(NCCCl)NCCCl	3220.4	Standard polar	33892256
Aldoifosfamide,1TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC=O	2159.2	Semi standard non polar	33892256
Aldoifosfamide,1TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC=O	1973.2	Standard non polar	33892256
Aldoifosfamide,1TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC=O	2988.0	Standard polar	33892256
Aldoifosfamide,2TMS,isomer #1	C[Si](C)(C)OC=CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C	2218.8	Semi standard non polar	33892256
Aldoifosfamide,2TMS,isomer #1	C[Si](C)(C)OC=CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C	2127.2	Standard non polar	33892256
Aldoifosfamide,2TMS,isomer #1	C[Si](C)(C)OC=CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C	2771.8	Standard polar	33892256
Aldoifosfamide,2TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(OCCC=O)N(CCCl)[Si](C)(C)C	2193.6	Semi standard non polar	33892256
Aldoifosfamide,2TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(OCCC=O)N(CCCl)[Si](C)(C)C	2095.7	Standard non polar	33892256
Aldoifosfamide,2TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(OCCC=O)N(CCCl)[Si](C)(C)C	2561.1	Standard polar	33892256
Aldoifosfamide,3TMS,isomer #1	C[Si](C)(C)OC=CCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C	2262.6	Semi standard non polar	33892256
Aldoifosfamide,3TMS,isomer #1	C[Si](C)(C)OC=CCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C	2223.3	Standard non polar	33892256
Aldoifosfamide,3TMS,isomer #1	C[Si](C)(C)OC=CCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C	2543.2	Standard polar	33892256
Aldoifosfamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCOP(=O)(NCCCl)NCCCl	2484.9	Semi standard non polar	33892256
Aldoifosfamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCOP(=O)(NCCCl)NCCCl	2252.0	Standard non polar	33892256
Aldoifosfamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCOP(=O)(NCCCl)NCCCl	3262.6	Standard polar	33892256
Aldoifosfamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC=O	2423.9	Semi standard non polar	33892256
Aldoifosfamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC=O	2221.7	Standard non polar	33892256
Aldoifosfamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCC=O	3012.6	Standard polar	33892256
Aldoifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C	2671.6	Semi standard non polar	33892256
Aldoifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C	2549.7	Standard non polar	33892256
Aldoifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C	2860.3	Standard polar	33892256
Aldoifosfamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCC=O)N(CCCl)[Si](C)(C)C(C)(C)C	2673.9	Semi standard non polar	33892256
Aldoifosfamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCC=O)N(CCCl)[Si](C)(C)C(C)(C)C	2445.5	Standard non polar	33892256
Aldoifosfamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCC=O)N(CCCl)[Si](C)(C)C(C)(C)C	2713.7	Standard polar	33892256
Aldoifosfamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C	2910.6	Semi standard non polar	33892256
Aldoifosfamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C	2713.3	Standard non polar	33892256
Aldoifosfamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C	2757.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Aldoifosfamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zor-3790000000-6de4991d540fdb25ecad	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aldoifosfamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aldoifosfamide 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 - Aldoifosfamide 10V, Positive-QTOF	splash10-057i-6090000000-1430dc02a1a6d05a0ef7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aldoifosfamide 20V, Positive-QTOF	splash10-0a59-9000000000-22aeb8eca73f0446e9ed	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aldoifosfamide 40V, Positive-QTOF	splash10-08ir-9000000000-0c1e120b60e087bdf777	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aldoifosfamide 10V, Negative-QTOF	splash10-01t9-3090000000-47f8b09177079f2eff82	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aldoifosfamide 20V, Negative-QTOF	splash10-03di-9440000000-3e4b4b1eab5d2716995e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aldoifosfamide 40V, Negative-QTOF	splash10-004i-9100000000-ddd742ec6e60562672f9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aldoifosfamide 10V, Negative-QTOF	splash10-004i-0090000000-dc92791f6cc6d866bc69	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aldoifosfamide 20V, Negative-QTOF	splash10-001r-3930000000-44b28453b068415780e2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aldoifosfamide 40V, Negative-QTOF	splash10-001r-0900000000-84646643ba9440333119	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aldoifosfamide 10V, Positive-QTOF	splash10-004i-1090000000-2e357be8ddb1b4c03143	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aldoifosfamide 20V, Positive-QTOF	splash10-0api-5950000000-1c1676e1bfd7707bc890	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aldoifosfamide 40V, Positive-QTOF	splash10-0a4i-7900000000-60a3e007d394a390a9c1	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

Biological Properties

Cellular Locations

Cytoplasm

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

C16556

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

189733

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 Aldoifosfamide (HMDB0060588)

MOL for HMDB0060588 (Aldoifosfamide)

3D MOL for HMDB0060588 (Aldoifosfamide)

3D SDF for HMDB0060588 (Aldoifosfamide)

3D-SDF for HMDB0060588 (Aldoifosfamide)

PDB for HMDB0060588 (Aldoifosfamide)

3D PDB for HMDB0060588 (Aldoifosfamide)

SMILES for HMDB0060588 (Aldoifosfamide)

INCHI for HMDB0060588 (Aldoifosfamide)

Structure for HMDB0060588 (Aldoifosfamide)

3D Structure for HMDB0060588 (Aldoifosfamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra