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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:20:27 UTC

Update Date

2019-07-23 07:14:19 UTC

HMDB ID

HMDB0060432

Secondary Accession Numbers

HMDB60432

Metabolite Identification

Common Name

Alcophosphamide

Description

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. Detoxification of aldophosphamide may also be effected by enzymes, viz. Thus, NAD-linked oxidation and NADPH-linked reduction of aldophosphamide catalyzed by relevant erythrocyte enzymes were quantified. (PMID: 9394035 ) It has already been demonstrated that horse liver alcohol dehydrogenase catalyzes the reduction of aldophosphamide to alcophosphamide. (PMID: 8216347 )

Structure

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

HMDB0060432
     RDKit          3D
Alcophosphamide
 32 31  0  0  0  0  0  0  0  0999 V2000
   -0.4765   -1.9698   -1.6425 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755   -1.0542   -0.1883 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.1062   -2.0331    0.9411 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2238   -0.0401   -0.4076 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -0.8331   -0.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6147   -0.0019   -0.6931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7090    0.9212    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8249    1.7371    0.4732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720   -0.1321    0.1929 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3762    1.1681   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388    2.3244    0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3792    3.7944   -0.3850 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6000   -1.0117    0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9230   -0.9281    0.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9294    0.4311    0.2203 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280   -2.7582   -1.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0178   -1.3221   -2.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2816   -1.5612   -1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4730   -1.4295    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4942   -0.6872   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5942    0.5717   -1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6694    0.2601    1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7572    1.5015    0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3189    1.5224   -0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5414    1.3202   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429    1.4119   -0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004    2.4494    0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7064    2.4851    1.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1814   -2.0615    0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7767   -1.1727   -1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4917   -1.8586    0.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8718   -1.0435    1.8113 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  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
M  END

Structure #1
  Mrv0541 02241207002D          

 15 14  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
    2.8570   -0.2763    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
   -2.6345    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
    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
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  4  1  0  0  0  0
  2  8  1  0  0  0  0
  3  5  1  0  0  0  0
  3  9  1  0  0  0  0
  4 11  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 15  1  0  0  0  0
 13 15  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060432

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
BZGFIGVSVQRQBJ-UHFFFAOYSA-N

> <FORMULA>
C7H17Cl2N2O3P

> <MOLECULAR_WEIGHT>
279.101

> <EXACT_MASS>
278.035384346

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.778195424063554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.30

> <JCHEM_LOGP>
-0.645705447666667

> <ALOGPS_LOGS>
-1.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.93055664380815

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.835132209828515

> <JCHEM_PKA_STRONGEST_BASIC>
-0.06849140925031882

> <JCHEM_POLAR_SURFACE_AREA>
75.79

> <JCHEM_REFRACTIVITY>
61.8427

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alcophosphamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060432
     RDKit          3D
Alcophosphamide
 32 31  0  0  0  0  0  0  0  0999 V2000
   -0.4765   -1.9698   -1.6425 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755   -1.0542   -0.1883 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.1062   -2.0331    0.9411 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2238   -0.0401   -0.4076 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -0.8331   -0.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6147   -0.0019   -0.6931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7090    0.9212    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8249    1.7371    0.4732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720   -0.1321    0.1929 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3762    1.1681   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388    2.3244    0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3792    3.7944   -0.3850 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6000   -1.0117    0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9230   -0.9281    0.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9294    0.4311    0.2203 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280   -2.7582   -1.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0178   -1.3221   -2.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2816   -1.5612   -1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4730   -1.4295    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4942   -0.6872   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5942    0.5717   -1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6694    0.2601    1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7572    1.5015    0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3189    1.5224   -0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5414    1.3202   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429    1.4119   -0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004    2.4494    0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7064    2.4851    1.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1814   -2.0615    0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7767   -1.1727   -1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4917   -1.8586    0.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8718   -1.0435    1.8113 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  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         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       5.333  -0.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.770   0.224   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       0.578  -0.531   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.703   1.334   0.000  0.00  0.00           O+0
HETATM   15  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   12                                                       
CONECT    7    1   14                                                       
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10   15                                                            
CONECT   11    4    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    HMDB0060432
HETATM    1  N1  UNL     1      -0.476  -1.970  -1.643  1.00  0.00           N  
HETATM    2  P1  UNL     1      -0.076  -1.054  -0.188  1.00  0.00           P  
HETATM    3  O1  UNL     1       0.106  -2.033   0.941  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.224  -0.040  -0.408  1.00  0.00           O  
HETATM    5  C1  UNL     1       2.362  -0.833  -0.499  1.00  0.00           C  
HETATM    6  C2  UNL     1       3.615  -0.002  -0.693  1.00  0.00           C  
HETATM    7  C3  UNL     1       3.709   0.921   0.523  1.00  0.00           C  
HETATM    8  O3  UNL     1       4.825   1.737   0.473  1.00  0.00           O  
HETATM    9  N2  UNL     1      -1.572  -0.132   0.193  1.00  0.00           N  
HETATM   10  C4  UNL     1      -1.376   1.168  -0.177  1.00  0.00           C  
HETATM   11  C5  UNL     1      -2.039   2.324   0.470  1.00  0.00           C  
HETATM   12 CL1  UNL     1      -1.379   3.794  -0.385  1.00  0.00          CL  
HETATM   13  C6  UNL     1      -2.600  -1.012   0.053  1.00  0.00           C  
HETATM   14  C7  UNL     1      -3.923  -0.928   0.699  1.00  0.00           C  
HETATM   15 CL2  UNL     1      -4.929   0.431   0.220  1.00  0.00          CL  
HETATM   16  H1  UNL     1      -1.128  -2.758  -1.377  1.00  0.00           H  
HETATM   17  H2  UNL     1      -1.018  -1.322  -2.292  1.00  0.00           H  
HETATM   18  H3  UNL     1       2.282  -1.561  -1.355  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.473  -1.430   0.434  1.00  0.00           H  
HETATM   20  H5  UNL     1       4.494  -0.687  -0.703  1.00  0.00           H  
HETATM   21  H6  UNL     1       3.594   0.572  -1.629  1.00  0.00           H  
HETATM   22  H7  UNL     1       3.669   0.260   1.410  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.757   1.501   0.529  1.00  0.00           H  
HETATM   24  H9  UNL     1       5.319   1.522  -0.371  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.541   1.320  -1.301  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.243   1.412  -0.087  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.100   2.449   0.393  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.706   2.485   1.531  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.181  -2.061   0.354  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.777  -1.173  -1.077  1.00  0.00           H  
HETATM   31  H16 UNL     1      -4.492  -1.859   0.370  1.00  0.00           H  
HETATM   32  H17 UNL     1      -3.872  -1.044   1.811  1.00  0.00           H  
CONECT    1    2   16   17
CONECT    2    3    3    4    9
CONECT    4    5
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8   22   23
CONECT    8   24
CONECT    9   10   13
CONECT   10   11   25   26
CONECT   11   12   27   28
CONECT   13   14   29   30
CONECT   14   15   31   32
END

HMDB0060432
     RDKit          3D
Alcophosphamide
 32 31  0  0  0  0  0  0  0  0999 V2000
   -0.4765   -1.9698   -1.6425 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755   -1.0542   -0.1883 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.1062   -2.0331    0.9411 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2238   -0.0401   -0.4076 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -0.8331   -0.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6147   -0.0019   -0.6931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7090    0.9212    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8249    1.7371    0.4732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720   -0.1321    0.1929 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3762    1.1681   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388    2.3244    0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3792    3.7944   -0.3850 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6000   -1.0117    0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9230   -0.9281    0.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9294    0.4311    0.2203 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280   -2.7582   -1.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0178   -1.3221   -2.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2816   -1.5612   -1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4730   -1.4295    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4942   -0.6872   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5942    0.5717   -1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6694    0.2601    1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7572    1.5015    0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3189    1.5224   -0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5414    1.3202   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429    1.4119   -0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004    2.4494    0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7064    2.4851    1.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1814   -2.0615    0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7767   -1.1727   -1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4917   -1.8586    0.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8718   -1.0435    1.8113 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  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 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-({amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propan-1-ol

Traditional Name

alcophosphamide

CAS Registry Number

Not Available

SMILES

NP(=O)(OCCCO)N(CCCl)CCCl

InChI Identifier

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

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

nitrogen mustard (CHEBI:80559 )

Ontology

Not Available

Liver (HMDB: HMDB0060432)
Kidney (HMDB: HMDB0060432)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060432)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060432)

Process

Not Available

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	18.8 g/L	ALOGPS
logP	0.3	ALOGPS
logP	-0.65	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	13.84	ChemAxon
pKa (Strongest Basic)	-0.068	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.79 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	61.84 m³·mol⁻¹	ChemAxon
Polarizability	25.78 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]+	151.142	30932474
DeepCCS	[M-H]-	148.481	30932474
DeepCCS	[M-2H]-	184.178	30932474
DeepCCS	[M+Na]+	158.778	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]-	155.2	32859911
AllCCS	[M+Na-2H]-	156.7	32859911
AllCCS	[M+HCOO]-	158.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alcophosphamide	NP(=O)(OCCCO)N(CCCl)CCCl	2927.9	Standard polar	33892256
Alcophosphamide	NP(=O)(OCCCO)N(CCCl)CCCl	1941.6	Standard non polar	33892256
Alcophosphamide	NP(=O)(OCCCO)N(CCCl)CCCl	2073.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Alcophosphamide,1TMS,isomer #1	C[Si](C)(C)OCCCOP(N)(=O)N(CCCl)CCCl	2182.7	Semi standard non polar	33892256
Alcophosphamide,1TMS,isomer #2	C[Si](C)(C)NP(=O)(OCCCO)N(CCCl)CCCl	2179.0	Semi standard non polar	33892256
Alcophosphamide,2TMS,isomer #1	C[Si](C)(C)NP(=O)(OCCCO[Si](C)(C)C)N(CCCl)CCCl	2189.7	Semi standard non polar	33892256
Alcophosphamide,2TMS,isomer #1	C[Si](C)(C)NP(=O)(OCCCO[Si](C)(C)C)N(CCCl)CCCl	2162.5	Standard non polar	33892256
Alcophosphamide,2TMS,isomer #1	C[Si](C)(C)NP(=O)(OCCCO[Si](C)(C)C)N(CCCl)CCCl	2674.8	Standard polar	33892256
Alcophosphamide,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCCO)N(CCCl)CCCl	2313.2	Semi standard non polar	33892256
Alcophosphamide,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCCO)N(CCCl)CCCl	2229.6	Standard non polar	33892256
Alcophosphamide,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)P(=O)(OCCCO)N(CCCl)CCCl	2748.3	Standard polar	33892256
Alcophosphamide,3TMS,isomer #1	C[Si](C)(C)OCCCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C	2326.7	Semi standard non polar	33892256
Alcophosphamide,3TMS,isomer #1	C[Si](C)(C)OCCCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C	2332.5	Standard non polar	33892256
Alcophosphamide,3TMS,isomer #1	C[Si](C)(C)OCCCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C)[Si](C)(C)C	2511.7	Standard polar	33892256
Alcophosphamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCOP(N)(=O)N(CCCl)CCCl	2428.2	Semi standard non polar	33892256
Alcophosphamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NP(=O)(OCCCO)N(CCCl)CCCl	2451.3	Semi standard non polar	33892256
Alcophosphamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NP(=O)(OCCCO[Si](C)(C)C(C)(C)C)N(CCCl)CCCl	2681.5	Semi standard non polar	33892256
Alcophosphamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NP(=O)(OCCCO[Si](C)(C)C(C)(C)C)N(CCCl)CCCl	2591.2	Standard non polar	33892256
Alcophosphamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NP(=O)(OCCCO[Si](C)(C)C(C)(C)C)N(CCCl)CCCl	2845.7	Standard polar	33892256
Alcophosphamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCCO)N(CCCl)CCCl	2744.2	Semi standard non polar	33892256
Alcophosphamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCCO)N(CCCl)CCCl	2608.5	Standard non polar	33892256
Alcophosphamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)P(=O)(OCCCO)N(CCCl)CCCl	2841.9	Standard polar	33892256
Alcophosphamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3003.8	Semi standard non polar	33892256
Alcophosphamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2844.6	Standard non polar	33892256
Alcophosphamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCOP(=O)(N(CCCl)CCCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2734.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Alcophosphamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01r6-4940000000-44137bb9687171ae5e54	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alcophosphamide GC-MS (1 TMS) - 70eV, Positive	splash10-0uk9-6590000000-496c0522af4655a53491	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alcophosphamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alcophosphamide 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 - Alcophosphamide 10V, Positive-QTOF	splash10-03fr-2090000000-b940569200b9a7c02bf5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcophosphamide 20V, Positive-QTOF	splash10-052f-9100000000-3a2c5dc0e1431a7c053b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcophosphamide 40V, Positive-QTOF	splash10-01ox-9300000000-f8dea9ffabf8fb46f226	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcophosphamide 10V, Negative-QTOF	splash10-016r-0490000000-70efe216a63fd9566444	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcophosphamide 20V, Negative-QTOF	splash10-0j4i-9240000000-82aeb95e51da24c19738	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcophosphamide 40V, Negative-QTOF	splash10-0udu-2910000000-e03eb5db4480b26b8da8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcophosphamide 10V, Positive-QTOF	splash10-004i-0390000000-951aac3e64aef3d58ff3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcophosphamide 20V, Positive-QTOF	splash10-00dl-0590000000-94cd86044965cd9259c3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcophosphamide 40V, Positive-QTOF	splash10-01ox-9100000000-7e0b86a6e77045907faf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcophosphamide 10V, Negative-QTOF	splash10-004i-0090000000-b4917fb5e83afb1e94df	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcophosphamide 20V, Negative-QTOF	splash10-004i-1190000000-cc6f126e02e531db1d39	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcophosphamide 40V, Negative-QTOF	splash10-0a6r-4910000000-c52af6ec588614247557	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

Not Available

Name	SMPDB/PathBank	KEGG

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

C16551

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

98612

PDB ID

Not Available

ChEBI ID

80559

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 ]
Parekh HK, Sladek NE: NADPH-dependent enzyme-catalyzed reduction of aldophosphamide, the pivotal metabolite of cyclophosphamide. Biochem Pharmacol. 1993 Sep 14;46(6):1043-52. [PubMed:8216347 ]

Enzymes

Enzyme Details

1. Alcohol dehydrogenase 4

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH4
Uniprot ID:: P08319
Molecular weight:: 40221.335

Reactions

Aldophosphamide + NADH + Hydrogen Ion → Alcophosphamide + NAD	details

Enzyme Details

2. Alcohol dehydrogenase class-3

General function:: Involved in zinc ion binding
Specific function:: Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:: ADH5
Uniprot ID:: P11766
Molecular weight:: 39723.945

Reactions

Aldophosphamide + NADH + Hydrogen Ion → Alcophosphamide + NAD	details

Enzyme Details

3. Alcohol dehydrogenase 1B

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1B
Uniprot ID:: P00325
Molecular weight:: 39835.17

Reactions

Aldophosphamide + NADH + Hydrogen Ion → Alcophosphamide + NAD	details

Enzyme Details

4. Alcohol dehydrogenase class 4 mu/sigma chain

General function:: Involved in zinc ion binding
Specific function:: Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:: ADH7
Uniprot ID:: P40394
Molecular weight:: 41480.985

Reactions

Aldophosphamide + NADH + Hydrogen Ion → Alcophosphamide + NAD	details

Enzyme Details

5. Alcohol dehydrogenase 1A

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1A
Uniprot ID:: P07327
Molecular weight:: 39858.37

Reactions

Aldophosphamide + NADH + Hydrogen Ion → Alcophosphamide + NAD	details

Enzyme Details

6. Alcohol dehydrogenase 6

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH6
Uniprot ID:: P28332
Molecular weight:: 39072.275

Reactions

Aldophosphamide + NADH + Hydrogen Ion → Alcophosphamide + NAD	details

Enzyme Details

7. Alcohol dehydrogenase 1C

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1C
Uniprot ID:: P00326
Molecular weight:: 39867.27

Reactions

Aldophosphamide + NADH + Hydrogen Ion → Alcophosphamide + NAD	details

Showing metabocard for Alcophosphamide (HMDB0060432)

MOL for HMDB0060432 (Alcophosphamide)

3D MOL for HMDB0060432 (Alcophosphamide)

3D SDF for HMDB0060432 (Alcophosphamide)

3D-SDF for HMDB0060432 (Alcophosphamide)

PDB for HMDB0060432 (Alcophosphamide)

3D PDB for HMDB0060432 (Alcophosphamide)

SMILES for HMDB0060432 (Alcophosphamide)

INCHI for HMDB0060432 (Alcophosphamide)

Structure for HMDB0060432 (Alcophosphamide)

3D Structure for HMDB0060432 (Alcophosphamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions