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Showing metabocard for 4-Hydroxycyclophosphamide (HMDB0013856)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:14 UTC
Update Date2021-09-14 15:20:33 UTC
HMDB IDHMDB0013856
Secondary Accession Numbers
  • HMDB13856
Metabolite Identification
Common Name4-Hydroxycyclophosphamide
Description4-Hydroxycyclophosphamide is a primary activation metabolite of cyclophosphamide and of mafosfamide (an experimental drug) after they partially metabolized by cytochrome P450 (PMID: 12021633 ). Cyclophosphamide is a chemotherapeutic used to suppress the immune system and to treat several cancers including lymphoma, multiple myeloma, leukemia, ovarian cancer, breast cancer and small cell lung cancer. After cyclphosphamide is converted to 4-hydroxycyclophosphamide it is then partially tautomerized into aldophosphamide, which easily enters live cells whereupon it is partially detoxified into inactive carboxycyclophosphamide by the enzyme ALDH. 4-Hydroxycyclophosphamide is also an intermediate metabolite in the formation of phosphoramide mustard, the active metabolite, and acrolein, the metabolite responsible for much of the toxicity associated with cyclophosphamides (PMID: 7059981 ). 4-Hydroxycyclophosphamide is not cytotoxic at physiologic pH, readily diffuses into cells and spontaneously decomposes into the active phosphoramide mustard. In human liver microsomes, 4-Hydroxycyclophosphamide formation correlates with known phenotypic markers of CYP2B6 activity, specifically formation of (S)-2-ethyl-1,5-dimethyl-3,3-diphenyl pyrrolidine and hydroxybupropion. In addition, it is reported that the CYP2B6 genotype is not consistently related to 4-Hydroxycyclophosphamide formation in vitro or in vivo (PMID: 21976622 ). 4-Hydroxycyclophosphamide is only found in individuals who have consumed the drug cyclophosphamide.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0013856 (4-Hydroxycyclophosphamide)

  Mrv0541 06191310212D          

 15 15  0  0  0  0            999 V2000
    9.5786   -3.4674    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.9798   -2.7483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1815   -4.1864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7556   -3.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3099   -3.8600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5497   -2.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7267   -2.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3298   -2.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3504   -4.1992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6075   -4.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9464   -1.3146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1262   -4.9391    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.6366   -6.3309    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.2107   -5.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9533   -4.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  8  1  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
  7  6  1  0  0  0  0
M  END
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3D MOL for HMDB0013856 (4-Hydroxycyclophosphamide)

HMDB0013856
     RDKit          3D
4-Hydroxycyclophosphamide
 30 30  0  0  0  0  0  0  0  0999 V2000
   -0.3432   -1.8673    1.6329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4817   -0.6995    0.6586 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.0873   -0.1704    0.2072 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7649   -1.2125   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2243   -1.3861   -0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495   -1.6094    1.4520 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2895    1.1656   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5733    1.8208    0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5927    3.5286   -0.2812 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4996    0.4886    1.3843 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8591    0.1577    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0422   -1.2138    1.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9898    0.4461   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9729   -0.2808   -1.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411   -1.3138   -0.6891 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835   -1.1630   -1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2708   -2.1911   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9021   -0.7217   -0.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4613   -2.4331   -0.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2346    1.2846   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4713    1.8517    0.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4840    1.2919    0.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5785    1.9618    1.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3517    1.4576    1.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5946    0.7647    1.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9888   -1.4615    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0258    0.2407   -0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8457    1.5353   -0.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997   -0.7070   -2.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2318    0.4354   -1.7713 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
  3  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15  2  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
 10 24  1  0
 11 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
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3D SDF for HMDB0013856 (4-Hydroxycyclophosphamide)

  Mrv0541 06191310212D          

 15 15  0  0  0  0            999 V2000
    9.5786   -3.4674    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.9798   -2.7483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1815   -4.1864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7556   -3.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3099   -3.8600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5497   -2.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7267   -2.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3298   -2.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3504   -4.1992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6075   -4.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9464   -1.3146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1262   -4.9391    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.6366   -6.3309    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.2107   -5.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9533   -4.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  8  1  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
  7  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013856

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CCOP(=O)(N1)N(CCCl)CCCl

> <INCHI_IDENTIFIER>
InChI=1S/C7H15Cl2N2O3P/c8-2-4-11(5-3-9)15(13)10-7(12)1-6-14-15/h7,12H,1-6H2,(H,10,13)

> <INCHI_KEY>
RANONBLIHMVXAJ-UHFFFAOYSA-N

> <FORMULA>
C7H15Cl2N2O3P

> <MOLECULAR_WEIGHT>
277.085

> <EXACT_MASS>
276.019734282

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.572307460036633

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[bis(2-chloroethyl)amino]-4-hydroxy-1,3,2λ⁵-oxazaphosphinan-2-one

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
-0.05733287299999987

> <ALOGPS_LOGS>
-1.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.061607142859263

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.67954718471601

> <JCHEM_PKA_STRONGEST_BASIC>
0.0051739710010082485

> <JCHEM_POLAR_SURFACE_AREA>
61.8

> <JCHEM_REFRACTIVITY>
59.09440000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxycyclophosphamide

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0013856 (4-Hydroxycyclophosphamide)

HMDB0013856
     RDKit          3D
4-Hydroxycyclophosphamide
 30 30  0  0  0  0  0  0  0  0999 V2000
   -0.3432   -1.8673    1.6329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4817   -0.6995    0.6586 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.0873   -0.1704    0.2072 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7649   -1.2125   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2243   -1.3861   -0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495   -1.6094    1.4520 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2895    1.1656   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5733    1.8208    0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5927    3.5286   -0.2812 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4996    0.4886    1.3843 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8591    0.1577    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0422   -1.2138    1.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9898    0.4461   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9729   -0.2808   -1.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411   -1.3138   -0.6891 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835   -1.1630   -1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2708   -2.1911   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9021   -0.7217   -0.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4613   -2.4331   -0.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2346    1.2846   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4713    1.8517    0.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4840    1.2919    0.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5785    1.9618    1.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3517    1.4576    1.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5946    0.7647    1.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9888   -1.4615    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0258    0.2407   -0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8457    1.5353   -0.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997   -0.7070   -2.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2318    0.4354   -1.7713 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
  3  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15  2  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
 10 24  1  0
 11 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
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PDB for HMDB0013856 (4-Hydroxycyclophosphamide)

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1  P   UNK     0      17.880  -6.472   0.000  0.00  0.00           P+0
HETATM    2  N   UNK     0      18.629  -5.130   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      17.139  -7.815   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0      16.344  -6.504   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      19.245  -7.205   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      17.826  -3.820   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.290  -3.851   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.549  -5.193   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.587  -7.839   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.934  -9.141   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      18.567  -2.454   0.000  0.00  0.00           O+0
HETATM   12 Cl   UNK     0      13.302  -9.220   0.000  0.00  0.00          Cl+0
HETATM   13 Cl   UNK     0      17.988 -11.818   0.000  0.00  0.00          Cl+0
HETATM   14  C   UNK     0      17.193 -10.491   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.846  -9.188   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6                                                       
CONECT    3    1    9   10                                                  
CONECT    4    1    8                                                       
CONECT    5    1                                                            
CONECT    6    2   11    7                                                  
CONECT    7    8    6                                                       
CONECT    8    7    4                                                       
CONECT    9    3   15                                                       
CONECT   10    3   14                                                       
CONECT   11    6                                                            
CONECT   12   15                                                            
CONECT   13   14                                                            
CONECT   14   13   10                                                       
CONECT   15   12    9                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END
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3D PDB for HMDB0013856 (4-Hydroxycyclophosphamide)

COMPND    HMDB0013856
HETATM    1  O1  UNL     1      -0.343  -1.867   1.633  1.00  0.00           O  
HETATM    2  P1  UNL     1      -0.482  -0.699   0.659  1.00  0.00           P  
HETATM    3  N1  UNL     1       1.087  -0.170   0.207  1.00  0.00           N  
HETATM    4  C1  UNL     1       1.765  -1.212  -0.449  1.00  0.00           C  
HETATM    5  C2  UNL     1       3.224  -1.386  -0.259  1.00  0.00           C  
HETATM    6 CL1  UNL     1       3.649  -1.609   1.452  1.00  0.00          CL  
HETATM    7  C3  UNL     1       1.289   1.166  -0.103  1.00  0.00           C  
HETATM    8  C4  UNL     1       2.573   1.821   0.314  1.00  0.00           C  
HETATM    9 CL2  UNL     1       2.593   3.529  -0.281  1.00  0.00          CL  
HETATM   10  N2  UNL     1      -1.500   0.489   1.384  1.00  0.00           N  
HETATM   11  C5  UNL     1      -2.859   0.158   0.962  1.00  0.00           C  
HETATM   12  O2  UNL     1      -3.042  -1.214   1.148  1.00  0.00           O  
HETATM   13  C6  UNL     1      -2.990   0.446  -0.496  1.00  0.00           C  
HETATM   14  C7  UNL     1      -1.973  -0.281  -1.342  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.341  -1.314  -0.689  1.00  0.00           O  
HETATM   16  H1  UNL     1       1.483  -1.163  -1.542  1.00  0.00           H  
HETATM   17  H2  UNL     1       1.271  -2.191  -0.132  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.902  -0.722  -0.768  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.461  -2.433  -0.711  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.235   1.285  -1.231  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.471   1.852   0.254  1.00  0.00           H  
HETATM   22  H7  UNL     1       3.484   1.292   0.102  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.579   1.962   1.461  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.352   1.458   1.082  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.595   0.765   1.520  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.989  -1.462   1.313  1.00  0.00           H  
HETATM   27  H12 UNL     1      -4.026   0.241  -0.858  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.846   1.535  -0.637  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.500  -0.707  -2.220  1.00  0.00           H  
HETATM   30  H15 UNL     1      -1.232   0.435  -1.771  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10   15
CONECT    3    4    7
CONECT    4    5   16   17
CONECT    5    6   18   19
CONECT    7    8   20   21
CONECT    8    9   22   23
CONECT   10   11   24
CONECT   11   12   13   25
CONECT   12   26
CONECT   13   14   27   28
CONECT   14   15   29   30
END
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SMILES for HMDB0013856 (4-Hydroxycyclophosphamide)

OC1CCOP(=O)(N1)N(CCCl)CCCl
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INCHI for HMDB0013856 (4-Hydroxycyclophosphamide)

InChI=1S/C7H15Cl2N2O3P/c8-2-4-11(5-3-9)15(13)10-7(12)1-6-14-15/h7,12H,1-6H2,(H,10,13)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Tetrahydro-2-(bis(2-chloroethyl)amino)-2H-1,3,2-oxazaphosphorin-4-ol 2-oxideChEBI
4-Hydroxycyclophosphamide, (cis)-isomerHMDB
4-Hydroxycyclophosphamide, (trans)-isomerHMDB
Chemical FormulaC7H15Cl2N2O3P
Average Molecular Weight277.085
Monoisotopic Molecular Weight276.019734282
IUPAC Name2-[bis(2-chloroethyl)amino]-4-hydroxy-1,3,2λ⁵-oxazaphosphinan-2-one
Traditional Name4-hydroxycyclophosphamide
CAS Registry Number40277-05-2
SMILES
OC1CCOP(=O)(N1)N(CCCl)CCCl
InChI Identifier
InChI=1S/C7H15Cl2N2O3P/c8-2-4-11(5-3-9)15(13)10-7(12)1-6-14-15/h7,12H,1-6H2,(H,10,13)
InChI KeyRANONBLIHMVXAJ-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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassNitrogen mustard compounds
Direct ParentNitrogen mustard compounds
Alternative Parents
Substituents
  • Nitrogen mustard
  • Phosphoric monoester diamide
  • Organic phosphoric acid derivative
  • Oxazaphosphinane
  • Organic phosphoric acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Alkanolamine
  • Oxacycle
  • Alkyl chloride
  • Organopnictogen compound
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Alkyl halide
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC07643
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Hydroxycyclophosphamide
METLIN IDNot Available
PubChem Compound99735
PDB IDNot Available
ChEBI ID1864
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Griskevicius L, Meurling L, Hassan M: Simple method based on fluorescent detection for the determination of 4-hydroxycyclophosphamide in plasma. Ther Drug Monit. 2002 Jun;24(3):405-9. doi: 10.1097/00007691-200206000-00013. [PubMed:12021633 ]
  2. Low JE, Borch RF, Sladek NE: Conversion of 4-hydroperoxycyclophosphamide and 4-hydroxycyclophosphamide to phosphoramide mustard and acrolein mediated by bifunctional catalysis. Cancer Res. 1982 Mar;42(3):830-7. [PubMed:7059981 ]
  3. Raccor BS, Claessens AJ, Dinh JC, Park JR, Hawkins DS, Thomas SS, Makar KW, McCune JS, Totah RA: Potential contribution of cytochrome P450 2B6 to hepatic 4-hydroxycyclophosphamide formation in vitro and in vivo. Drug Metab Dispos. 2012 Jan;40(1):54-63. doi: 10.1124/dmd.111.039347. Epub 2011 Oct 5. [PubMed:21976622 ]

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preiss R, Schmidt R, Baumann F, Hanschmann H, Hauss J, Geissler F, Pahlig H, Ratzewiss B: Measurement of 4-hydroxylation of ifosfamide in human liver microsomes using the estimation of free and protein-bound acrolein and codetermination of keto- and carboxyifosfamide. J Cancer Res Clin Oncol. 2002 Jul;128(7):385-92. Epub 2002 Jun 11. [PubMed:12136253 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
2. Cytochrome P450 2C9
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
3. Cytochrome P450 2C19
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
4. Cytochrome P450 2D6
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
5. Cytochrome P450 2C18
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
6. Cytochrome P450 2B6
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preiss R, Schmidt R, Baumann F, Hanschmann H, Hauss J, Geissler F, Pahlig H, Ratzewiss B: Measurement of 4-hydroxylation of ifosfamide in human liver microsomes using the estimation of free and protein-bound acrolein and codetermination of keto- and carboxyifosfamide. J Cancer Res Clin Oncol. 2002 Jul;128(7):385-92. Epub 2002 Jun 11. [PubMed:12136253 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
7. Cytochrome P450 3A7
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
8. Cytochrome P450 2C8
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
9. Cytochrome P450 2A6
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular weight:
56517.005
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details
1. Multidrug resistance protein 1
General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Wang E, Lew K, Barecki M, Casciano CN, Clement RP, Johnson WW: Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4. Chem Res Toxicol. 2001 Dec;14(12):1596-603. [PubMed:11743742 ]