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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 19:13:59 UTC

Update Date

2019-07-23 07:14:52 UTC

HMDB ID

HMDB0060693

Secondary Accession Numbers

HMDB60693

Metabolite Identification

Common Name

Alcoifosfamide

Description

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

Structure

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

HMDB0060693
     RDKit          3D
Alcoifosfamide
 32 31  0  0  0  0  0  0  0  0999 V2000
    0.4971    0.3717    1.4526 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8601   -0.1042   -0.0270 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4944    1.4194   -0.6976 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7680    1.7588   -0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    3.2683    0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2189    4.2531   -1.0969 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9397   -1.3204    0.1287 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673   -2.5807   -0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3942   -3.1438    0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7903   -3.8894   -0.6487 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5663   -0.2749   -0.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -0.3338    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828    0.8013   -0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9747    0.4940   -0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1673    0.1316    1.2855 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6743    1.2153   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6021    1.7018   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098    1.1761    0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7225    3.5062    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0119    3.3150    1.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8970   -1.1964    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3780   -2.6194   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3886   -3.2759   -0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307   -4.0196    1.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0392   -2.4295    1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3215   -0.2012    1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2001   -1.2926    0.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3666    1.3069   -1.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2972    1.6557    0.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2898   -0.4182   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716    1.3395   -0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8361   -0.6147    1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
M  END

 
  Mrv0541 06181312132D          
 
 15 14  0  0  0  0            999 V2000
   14.9906  -10.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9941  -11.3392    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.2776  -10.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2845  -11.7628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7208  -11.7387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2776  -10.9258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5646  -10.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2982  -12.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8551  -10.0992    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.0181  -12.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4105  -11.3209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1355  -11.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8555  -11.2834    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.0290  -13.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7491  -14.1982    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
M  END
> <DATABASE_ID>
HMDB0060693

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCCOP(=O)(NCCCl)NCCCl

> <INCHI_IDENTIFIER>
InChI=1S/C7H17Cl2N2O3P/c8-2-4-10-15(13,11-5-3-9)14-7-1-6-12/h12H,1-7H2,(H2,10,11,13)

> <INCHI_KEY>
JOAQXFLTMDRBOD-UHFFFAOYSA-N

> <FORMULA>
C7H17Cl2N2O3P

> <MOLECULAR_WEIGHT>
279.101

> <EXACT_MASS>
278.035384346

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.132558630724176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-({bis[(2-chloroethyl)amino]phosphoryl}oxy)propan-1-ol

> <ALOGPS_LOGP>
-0.16

> <JCHEM_LOGP>
-0.645705447666667

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.92692570557978

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.416729837761103

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3185401644952806

> <JCHEM_POLAR_SURFACE_AREA>
70.59

> <JCHEM_REFRACTIVITY>
61.84270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.97e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alcoifosfamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060693
     RDKit          3D
Alcoifosfamide
 32 31  0  0  0  0  0  0  0  0999 V2000
    0.4971    0.3717    1.4526 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8601   -0.1042   -0.0270 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4944    1.4194   -0.6976 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7680    1.7588   -0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    3.2683    0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2189    4.2531   -1.0969 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9397   -1.3204    0.1287 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673   -2.5807   -0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3942   -3.1438    0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7903   -3.8894   -0.6487 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5663   -0.2749   -0.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -0.3338    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828    0.8013   -0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9747    0.4940   -0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1673    0.1316    1.2855 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6743    1.2153   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6021    1.7018   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098    1.1761    0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7225    3.5062    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0119    3.3150    1.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8970   -1.1964    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3780   -2.6194   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3886   -3.2759   -0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307   -4.0196    1.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0392   -2.4295    1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3215   -0.2012    1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2001   -1.2926    0.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3666    1.3069   -1.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2972    1.6557    0.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2898   -0.4182   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716    1.3395   -0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8361   -0.6147    1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  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      27.982 -19.623   0.000  0.00  0.00           N+0
HETATM    2  P   UNK     0      27.989 -21.166   0.000  0.00  0.00           P+0
HETATM    3  C   UNK     0      26.651 -18.852   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      26.664 -21.957   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      29.346 -21.912   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0      26.651 -20.395   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      25.321 -19.623   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.690 -23.494   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0      23.996 -18.852   0.000  0.00  0.00          Cl+0
HETATM   10  C   UNK     0      28.034 -24.246   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.633 -21.132   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.986 -21.876   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      33.330 -21.062   0.000  0.00  0.00          Cl+0
HETATM   14  C   UNK     0      28.054 -25.751   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      29.398 -26.503   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                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0060693
HETATM    1  O1  UNL     1       0.497   0.372   1.453  1.00  0.00           O  
HETATM    2  P1  UNL     1       0.860  -0.104  -0.027  1.00  0.00           P  
HETATM    3  N1  UNL     1       1.494   1.419  -0.698  1.00  0.00           N  
HETATM    4  C1  UNL     1       2.768   1.759  -0.133  1.00  0.00           C  
HETATM    5  C2  UNL     1       2.699   3.268   0.245  1.00  0.00           C  
HETATM    6 CL1  UNL     1       2.219   4.253  -1.097  1.00  0.00          CL  
HETATM    7  N2  UNL     1       1.940  -1.320   0.129  1.00  0.00           N  
HETATM    8  C3  UNL     1       1.467  -2.581  -0.412  1.00  0.00           C  
HETATM    9  C4  UNL     1       0.394  -3.144   0.497  1.00  0.00           C  
HETATM   10 CL2  UNL     1      -0.790  -3.889  -0.649  1.00  0.00          CL  
HETATM   11  O2  UNL     1      -0.566  -0.275  -0.804  1.00  0.00           O  
HETATM   12  C5  UNL     1      -1.649  -0.334   0.084  1.00  0.00           C  
HETATM   13  C6  UNL     1      -2.583   0.801  -0.339  1.00  0.00           C  
HETATM   14  C7  UNL     1      -3.975   0.494  -0.003  1.00  0.00           C  
HETATM   15  O3  UNL     1      -4.167   0.132   1.285  1.00  0.00           O  
HETATM   16  H1  UNL     1       1.674   1.215  -1.753  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.602   1.702  -0.873  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.010   1.176   0.755  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.722   3.506   0.559  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.012   3.315   1.126  1.00  0.00           H  
HETATM   21  H6  UNL     1       2.897  -1.196   0.353  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.378  -2.619  -1.441  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.389  -3.276  -0.146  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.731  -4.020   1.102  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.039  -2.430   1.175  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.322  -0.201   1.109  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.200  -1.293   0.016  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.367   1.307  -1.236  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.297   1.656   0.481  1.00  0.00           H  
HETATM   30  H15 UNL     1      -4.290  -0.418  -0.637  1.00  0.00           H  
HETATM   31  H16 UNL     1      -4.672   1.340  -0.260  1.00  0.00           H  
HETATM   32  H17 UNL     1      -4.836  -0.615   1.364  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7   11
CONECT    3    4   16
CONECT    4    5   17   18
CONECT    5    6   19   20
CONECT    7    8   21
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   11   12
CONECT   12   13   26   27
CONECT   13   14   28   29
CONECT   14   15   30   31
CONECT   15   32
END

HMDB0060693
     RDKit          3D
Alcoifosfamide
 32 31  0  0  0  0  0  0  0  0999 V2000
    0.4971    0.3717    1.4526 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8601   -0.1042   -0.0270 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4944    1.4194   -0.6976 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7680    1.7588   -0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    3.2683    0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2189    4.2531   -1.0969 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9397   -1.3204    0.1287 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673   -2.5807   -0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3942   -3.1438    0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7903   -3.8894   -0.6487 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5663   -0.2749   -0.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -0.3338    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828    0.8013   -0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9747    0.4940   -0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1673    0.1316    1.2855 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6743    1.2153   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6021    1.7018   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098    1.1761    0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7225    3.5062    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0119    3.3150    1.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8970   -1.1964    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3780   -2.6194   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3886   -3.2759   -0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307   -4.0196    1.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0392   -2.4295    1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3215   -0.2012    1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2001   -1.2926    0.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3666    1.3069   -1.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2972    1.6557    0.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2898   -0.4182   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716    1.3395   -0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8361   -0.6147    1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₇H₁₇Cl₂N₂O₃P

Average Molecular Weight

279.101

Monoisotopic Molecular Weight

278.035384346

IUPAC Name

3-({bis[(2-chloroethyl)amino]phosphoryl}oxy)propan-1-ol

Traditional Name

alcoifosfamide

CAS Registry Number

Not Available

SMILES

OCCCOP(=O)(NCCCl)NCCCl

InChI Identifier

InChI=1S/C7H17Cl2N2O3P/c8-2-4-10-15(13,11-5-3-9)14-7-1-6-12/h12H,1-7H2,(H2,10,11,13)

InChI Key

JOAQXFLTMDRBOD-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
Alcohol
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphorodiamide (CHEBI:80565 )

Ontology

Not Available

Liver (HMDB: HMDB0060693)
Kidney (HMDB: HMDB0060693)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060693)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060693)

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	6.97 g/L	ALOGPS
logP	-0.16	ALOGPS
logP	-0.65	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	12.42	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	70.59 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	61.84 m³·mol⁻¹	ChemAxon
Polarizability	26.13 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]+	155.425	30932474
DeepCCS	[M-H]-	152.657	30932474
DeepCCS	[M-2H]-	188.383	30932474
DeepCCS	[M+Na]+	163.767	30932474
AllCCS	[M+H]+	156.4	32859911
AllCCS	[M+H-H2O]+	153.5	32859911
AllCCS	[M+NH4]+	159.2	32859911
AllCCS	[M+Na]+	160.0	32859911
AllCCS	[M-H]-	155.1	32859911
AllCCS	[M+Na-2H]-	156.5	32859911
AllCCS	[M+HCOO]-	158.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alcoifosfamide	OCCCOP(=O)(NCCCl)NCCCl	3144.4	Standard polar	33892256
Alcoifosfamide	OCCCOP(=O)(NCCCl)NCCCl	1939.7	Standard non polar	33892256
Alcoifosfamide	OCCCOP(=O)(NCCCl)NCCCl	2098.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Alcoifosfamide,1TMS,isomer #1	C[Si](C)(C)OCCCOP(=O)(NCCCl)NCCCl	2229.5	Semi standard non polar	33892256
Alcoifosfamide,1TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCCO	2189.5	Semi standard non polar	33892256
Alcoifosfamide,2TMS,isomer #1	C[Si](C)(C)OCCCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C	2209.1	Semi standard non polar	33892256
Alcoifosfamide,2TMS,isomer #1	C[Si](C)(C)OCCCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C	2136.2	Standard non polar	33892256
Alcoifosfamide,2TMS,isomer #1	C[Si](C)(C)OCCCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C	2734.8	Standard polar	33892256
Alcoifosfamide,2TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(OCCCO)N(CCCl)[Si](C)(C)C	2252.1	Semi standard non polar	33892256
Alcoifosfamide,2TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(OCCCO)N(CCCl)[Si](C)(C)C	2152.1	Standard non polar	33892256
Alcoifosfamide,2TMS,isomer #2	C[Si](C)(C)N(CCCl)P(=O)(OCCCO)N(CCCl)[Si](C)(C)C	2681.3	Standard polar	33892256
Alcoifosfamide,3TMS,isomer #1	C[Si](C)(C)OCCCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C	2292.4	Semi standard non polar	33892256
Alcoifosfamide,3TMS,isomer #1	C[Si](C)(C)OCCCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C	2220.7	Standard non polar	33892256
Alcoifosfamide,3TMS,isomer #1	C[Si](C)(C)OCCCOP(=O)(N(CCCl)[Si](C)(C)C)N(CCCl)[Si](C)(C)C	2479.8	Standard polar	33892256
Alcoifosfamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCOP(=O)(NCCCl)NCCCl	2460.1	Semi standard non polar	33892256
Alcoifosfamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(NCCCl)OCCCO	2461.7	Semi standard non polar	33892256
Alcoifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C	2703.3	Semi standard non polar	33892256
Alcoifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C	2575.3	Standard non polar	33892256
Alcoifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCOP(=O)(NCCCl)N(CCCl)[Si](C)(C)C(C)(C)C	2868.5	Standard polar	33892256
Alcoifosfamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCCO)N(CCCl)[Si](C)(C)C(C)(C)C	2722.2	Semi standard non polar	33892256
Alcoifosfamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCCO)N(CCCl)[Si](C)(C)C(C)(C)C	2528.4	Standard non polar	33892256
Alcoifosfamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P(=O)(OCCCO)N(CCCl)[Si](C)(C)C(C)(C)C	2838.2	Standard polar	33892256
Alcoifosfamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C	2977.3	Semi standard non polar	33892256
Alcoifosfamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C	2734.8	Standard non polar	33892256
Alcoifosfamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N(CCCl)[Si](C)(C)C(C)(C)C	2752.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Alcoifosfamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-3590000000-130f4f43222530513373	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alcoifosfamide GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9681000000-70c81713a46f22c7c9a4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alcoifosfamide 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 - Alcoifosfamide 10V, Positive-QTOF	splash10-06w9-5090000000-a566c82b383348b53db7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcoifosfamide 20V, Positive-QTOF	splash10-053u-9000000000-a0edd3a2929a323db21a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcoifosfamide 40V, Positive-QTOF	splash10-03gl-9000000000-a35e673df51ecc892b3f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcoifosfamide 10V, Negative-QTOF	splash10-004i-2190000000-c473564bcc31940c8271	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcoifosfamide 20V, Negative-QTOF	splash10-0ik9-9350000000-365f38e6482f562ee05a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcoifosfamide 40V, Negative-QTOF	splash10-004i-9100000000-8af3b8643312576e9a60	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcoifosfamide 10V, Positive-QTOF	splash10-004i-2090000000-86b071f18474d398bff6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcoifosfamide 20V, Positive-QTOF	splash10-0ab9-4950000000-ca23c2e57bd8df8555cb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcoifosfamide 40V, Positive-QTOF	splash10-0a4i-7900000000-537d813547e3c8df4c36	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcoifosfamide 10V, Negative-QTOF	splash10-004i-0090000000-b4917fb5e83afb1e94df	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcoifosfamide 20V, Negative-QTOF	splash10-004i-0490000000-d093b32c93c7294cdf96	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcoifosfamide 40V, Negative-QTOF	splash10-000l-0900000000-3b893db53272a44ec1ee	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

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

C16558

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10265589

PDB ID

Not Available

ChEBI ID

80565

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 Alcoifosfamide (HMDB0060693)

MOL for HMDB0060693 (Alcoifosfamide)

3D MOL for HMDB0060693 (Alcoifosfamide)

3D SDF for HMDB0060693 (Alcoifosfamide)

3D-SDF for HMDB0060693 (Alcoifosfamide)

PDB for HMDB0060693 (Alcoifosfamide)

3D PDB for HMDB0060693 (Alcoifosfamide)

SMILES for HMDB0060693 (Alcoifosfamide)

INCHI for HMDB0060693 (Alcoifosfamide)

Structure for HMDB0060693 (Alcoifosfamide)

3D Structure for HMDB0060693 (Alcoifosfamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra