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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-13 11:47:09 UTC

Update Date

2021-09-14 15:45:32 UTC

HMDB ID

HMDB0041905

Secondary Accession Numbers

HMDB0060598
HMDB0060972
HMDB41905
HMDB60598
HMDB60972

Metabolite Identification

Common Name

4-Hydroxyphenytoin

Description

4-Hydroxyphenytoin, also known as 4'-HPPH, belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. In humans, 4-hydroxyphenytoin is involved in the metabolic disorder called the phenytoin (antiarrhythmic) action pathway. 4-Hydroxyphenytoin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 4-Hydroxyphenytoin.

Structure

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

HMDB0041905
     RDKit          3D
4-Hydroxyphenytoin
 32 34  0  0  0  0  0  0  0  0999 V2000
    0.2797    3.8772    2.0431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    2.8384    1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2366    1.5902    1.3444 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2846    0.8622    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4115   -0.1042    0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9634   -0.5659   -1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0214   -1.4775   -1.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5263   -1.9265    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9988   -1.4861    1.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9613   -0.5918    1.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346    0.1334    0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043   -0.4574   -1.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6038   -1.1478   -1.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4571   -1.2423   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497   -1.9251   -0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0903   -0.6489    0.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958    0.0347    1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3846    1.9045   -0.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.7285   -2.2917 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3901    3.0328   -0.3093 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4363    4.5797    1.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195   -0.2545   -2.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4352   -1.8228   -2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3474   -2.6338    0.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4249   -1.8641    2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5457   -0.2448    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7443   -0.3878   -2.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8529   -1.5978   -2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3014   -2.0153    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7701   -0.7215    1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033    0.5043    2.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548    2.0301   -2.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  4 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 10  5  1  0
 17 11  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
M  END


  Mrv0541 09131211472D          

 20 22  0  0  0  0            999 V2000
    0.7248    4.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0822    4.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9797    3.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6342    4.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4277    3.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2284    4.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2903    3.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7805    4.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8424    3.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3793    3.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4834    3.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5874    4.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2639    2.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3438    1.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9313    2.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5188    1.3372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5988    2.1218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1395    5.0591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5207    2.3767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8288    0.6697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 13  2  0  0  0  0
 16 14  1  0  0  0  0
 17 14  2  0  0  0  0
 17 15  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041905

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=NC(C(O)=N1)(C1=CC=CC=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12N2O3/c18-12-8-6-11(7-9-12)15(10-4-2-1-3-5-10)13(19)16-14(20)17-15/h1-9,18H,(H2,16,17,19,20)

> <INCHI_KEY>
XEEDURHPFVXALT-UHFFFAOYSA-N

> <FORMULA>
C15H12N2O3

> <MOLECULAR_WEIGHT>
268.2674

> <EXACT_MASS>
268.08479226

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.76518086788886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(4-hydroxyphenyl)-4-phenyl-4H-imidazole-2,5-diol

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
3.097759990333333

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.427806237635401

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7618597893046495

> <JCHEM_PKA_STRONGEST_BASIC>
-1.212204000293153

> <JCHEM_POLAR_SURFACE_AREA>
85.41000000000001

> <JCHEM_REFRACTIVITY>
73.20660000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(4-hydroxyphenyl)-5-phenylimidazole-2,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041905
     RDKit          3D
4-Hydroxyphenytoin
 32 34  0  0  0  0  0  0  0  0999 V2000
    0.2797    3.8772    2.0431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    2.8384    1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2366    1.5902    1.3444 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2846    0.8622    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4115   -0.1042    0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9634   -0.5659   -1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0214   -1.4775   -1.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5263   -1.9265    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9988   -1.4861    1.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9613   -0.5918    1.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346    0.1334    0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043   -0.4574   -1.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6038   -1.1478   -1.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4571   -1.2423   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497   -1.9251   -0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0903   -0.6489    0.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958    0.0347    1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3846    1.9045   -0.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.7285   -2.2917 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3901    3.0328   -0.3093 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4363    4.5797    1.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195   -0.2545   -2.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4352   -1.8228   -2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3474   -2.6338    0.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4249   -1.8641    2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5457   -0.2448    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7443   -0.3878   -2.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8529   -1.5978   -2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3014   -2.0153    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7701   -0.7215    1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033    0.5043    2.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548    2.0301   -2.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  4 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 10  5  1  0
 17 11  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       1.353   8.299   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.153   8.619   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.829   6.835   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.184   7.475   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.798   5.690   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.293   7.475   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.275   5.690   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.324   8.619   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.306   6.835   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.708   6.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.769   6.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.830   8.299   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.493   3.961   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.508   2.496   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.738   4.866   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -0.968   2.496   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      -2.984   3.961   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      -5.860   9.444   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.972   4.437   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.414   1.250   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6    8   11                                                       
CONECT    7    9   11                                                       
CONECT    8    6   12                                                       
CONECT    9    7   12                                                       
CONECT   10    4    5   15                                                  
CONECT   11    6    7   15                                                  
CONECT   12    8    9   18                                                  
CONECT   13   15   16   19                                                  
CONECT   14   16   17   20                                                  
CONECT   15   10   11   13   17                                             
CONECT   16   13   14                                                       
CONECT   17   14   15                                                       
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0041905
HETATM    1  O1  UNL     1       0.280   3.877   2.043  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.298   2.838   1.092  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.237   1.590   1.344  1.00  0.00           N  
HETATM    4  C2  UNL     1       0.285   0.862   0.107  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.412  -0.104   0.073  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.963  -0.566  -1.084  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.021  -1.478  -1.099  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.526  -1.926   0.081  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.999  -1.486   1.285  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.961  -0.592   1.263  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.035   0.133   0.017  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.404  -0.457  -1.161  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.604  -1.148  -1.317  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.457  -1.242  -0.242  1.00  0.00           C  
HETATM   15  O2  UNL     1      -4.650  -1.925  -0.386  1.00  0.00           O  
HETATM   16  C13 UNL     1      -3.090  -0.649   0.949  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.896   0.035   1.093  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.385   1.905  -0.920  1.00  0.00           C  
HETATM   19  O3  UNL     1       0.460   1.728  -2.292  1.00  0.00           O  
HETATM   20  N2  UNL     1       0.390   3.033  -0.309  1.00  0.00           N  
HETATM   21  H1  UNL     1      -0.436   4.580   1.969  1.00  0.00           H  
HETATM   22  H2  UNL     1       1.620  -0.254  -2.035  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.435  -1.823  -2.035  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.347  -2.634   0.062  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.425  -1.864   2.219  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.546  -0.245   2.191  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.744  -0.388  -2.012  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.853  -1.598  -2.266  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.301  -2.015   0.382  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.770  -0.722   1.813  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.603   0.504   2.030  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.255   2.030  -2.857  1.00  0.00           H  
CONECT    1    2   21
CONECT    2    3    3   20
CONECT    3    4
CONECT    4    5   11   18
CONECT    5    6    6   10
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   26
CONECT   11   12   12   17
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15   16
CONECT   15   29
CONECT   16   17   17   30
CONECT   17   31
CONECT   18   19   20   20
CONECT   19   32
END

HMDB0041905
     RDKit          3D
4-Hydroxyphenytoin
 32 34  0  0  0  0  0  0  0  0999 V2000
    0.2797    3.8772    2.0431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    2.8384    1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2366    1.5902    1.3444 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2846    0.8622    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4115   -0.1042    0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9634   -0.5659   -1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0214   -1.4775   -1.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5263   -1.9265    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9988   -1.4861    1.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9613   -0.5918    1.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346    0.1334    0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043   -0.4574   -1.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6038   -1.1478   -1.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4571   -1.2423   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497   -1.9251   -0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0903   -0.6489    0.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958    0.0347    1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3846    1.9045   -0.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.7285   -2.2917 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3901    3.0328   -0.3093 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4363    4.5797    1.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195   -0.2545   -2.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4352   -1.8228   -2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3474   -2.6338    0.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4249   -1.8641    2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5457   -0.2448    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7443   -0.3878   -2.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8529   -1.5978   -2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3014   -2.0153    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7701   -0.7215    1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033    0.5043    2.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548    2.0301   -2.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  4 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 10  5  1  0
 17 11  1  0
  1 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Hydroxyphenyl)phenylhydantoin	ChEBI
(p-Hydroxyphenyl)phenylhydantoin	ChEBI
4-Hydroxydiphenylhydantoin	ChEBI
5-(4'-Hydroxyphenyl)-5-phenylhydantoin	ChEBI
5-(p-Hydroxyphenyl)-5-phenylhydantoin	ChEBI
Hydroxydiphenylhydantoin	ChEBI
Hydroxyphenytoin	ChEBI
p-Hydroxydiphenylhydantoin	ChEBI
p-Hydroxyphenytoin	ChEBI
Para-hydroxyphenytoin	ChEBI
5-(4-Hydroxyphenyl)-5-phenyl-2,4-imidazolidinedione	HMDB
5-(4-Hydroxyphenyl)-5-phenylhydantoin	HMDB
5-(p-Hydroxyphenyl)-5-phenyl-hydantoin	HMDB
Hydroxyphenytoin, (R)-isomer	HMDB
4'-HPPH	HMDB
4-HPPH	HMDB
Hydroxyphenytoin, (+-)-isomer	HMDB
Hydroxyphenytoin, (S)-isomer	HMDB
Hydroxyphenytoin, 11C-labeled	HMDB

Chemical Formula

C₁₅H₁₂N₂O₃

Average Molecular Weight

268.2674

Monoisotopic Molecular Weight

268.08479226

IUPAC Name

4-(4-hydroxyphenyl)-4-phenyl-4H-imidazole-2,5-diol

Traditional Name

5-(4-hydroxyphenyl)-5-phenylimidazole-2,4-diol

CAS Registry Number

2784-27-2

SMILES

OC1=NC(C(O)=N1)(C1=CC=CC=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H12N2O3/c18-12-8-6-11(7-9-12)15(10-4-2-1-3-5-10)13(19)16-14(20)17-15/h1-9,18H,(H2,16,17,19,20)

InChI Key

XEEDURHPFVXALT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Phenylhydantoins

Alternative Parents

Substituents

Diphenylmethane
5-phenylhydantoin
Phenylimidazolidine
Alpha-amino acid or derivatives
5-monosubstituted hydantoin
1-hydroxy-2-unsubstituted benzenoid
N-acyl urea
Phenol
Ureide
Monocyclic benzene moiety
Benzenoid
Dicarboximide
Urea
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

phenols (CHEBI:63804 )
imidazolidine-2,4-dione (CHEBI:63804 )

Ontology

Not Available

Urine (PMID: 4049465)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2362000)

Cellular substructure

Membrane (HMDB: HMDB0041905)

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	1.70	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.01	ALOGPS
logP	3.1	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	85.41 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.21 m³·mol⁻¹	ChemAxon
Polarizability	26.77 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	162.235	31661259
DarkChem	[M-H]-	160.713	31661259
DeepCCS	[M+H]+	163.246	30932474
DeepCCS	[M-H]-	160.888	30932474
DeepCCS	[M-2H]-	193.774	30932474
DeepCCS	[M+Na]+	169.339	30932474
AllCCS	[M+H]+	161.5	32859911
AllCCS	[M+H-H2O]+	157.6	32859911
AllCCS	[M+NH4]+	165.1	32859911
AllCCS	[M+Na]+	166.2	32859911
AllCCS	[M-H]-	162.7	32859911
AllCCS	[M+Na-2H]-	162.0	32859911
AllCCS	[M+HCOO]-	161.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyphenytoin	OC1=NC(C(O)=N1)(C1=CC=CC=C1)C1=CC=C(O)C=C1	3767.8	Standard polar	33892256
4-Hydroxyphenytoin	OC1=NC(C(O)=N1)(C1=CC=CC=C1)C1=CC=C(O)C=C1	2309.5	Standard non polar	33892256
4-Hydroxyphenytoin	OC1=NC(C(O)=N1)(C1=CC=CC=C1)C1=CC=C(O)C=C1	2670.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyphenytoin,1TMS,isomer #1	C[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O)C=C2)C(O)=N1	2498.1	Semi standard non polar	33892256
4-Hydroxyphenytoin,1TMS,isomer #2	C[Si](C)(C)OC1=NC(O)=NC1(C1=CC=CC=C1)C1=CC=C(O)C=C1	2492.7	Semi standard non polar	33892256
4-Hydroxyphenytoin,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)N=C(O)N=C2O)C=C1	2558.6	Semi standard non polar	33892256
4-Hydroxyphenytoin,2TMS,isomer #1	C[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O[Si](C)(C)C)C=C2)C(O)=N1	2505.3	Semi standard non polar	33892256
4-Hydroxyphenytoin,2TMS,isomer #2	C[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O)C=C2)C(O[Si](C)(C)C)=N1	2448.5	Semi standard non polar	33892256
4-Hydroxyphenytoin,2TMS,isomer #3	C[Si](C)(C)OC1=NC(O)=NC1(C1=CC=CC=C1)C1=CC=C(O[Si](C)(C)C)C=C1	2502.8	Semi standard non polar	33892256
4-Hydroxyphenytoin,3TMS,isomer #1	C[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O[Si](C)(C)C)C=C2)C(O[Si](C)(C)C)=N1	2540.9	Semi standard non polar	33892256
4-Hydroxyphenytoin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O)C=C2)C(O)=N1	2722.2	Semi standard non polar	33892256
4-Hydroxyphenytoin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(O)=NC1(C1=CC=CC=C1)C1=CC=C(O)C=C1	2717.9	Semi standard non polar	33892256
4-Hydroxyphenytoin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)N=C(O)N=C2O)C=C1	2795.1	Semi standard non polar	33892256
4-Hydroxyphenytoin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(O)=N1	2926.0	Semi standard non polar	33892256
4-Hydroxyphenytoin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=N1	2851.6	Semi standard non polar	33892256
4-Hydroxyphenytoin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=NC(O)=NC1(C1=CC=CC=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2922.8	Semi standard non polar	33892256
4-Hydroxyphenytoin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(O[Si](C)(C)C(C)(C)C)=N1	3072.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenytoin GC-MS (Non-derivatized) - 70eV, Positive	splash10-005c-2970000000-f2362aeb837caff92396	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenytoin GC-MS (3 TMS) - 70eV, Positive	splash10-01b9-5026900000-a7352e0820321c5e2123	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenytoin 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 - 4-Hydroxyphenytoin 10V, Positive-QTOF	splash10-014i-0290000000-2299e419930e3a97862c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 20V, Positive-QTOF	splash10-00kb-0960000000-45490c2de987f0b93b2d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 40V, Positive-QTOF	splash10-0gi1-1900000000-31738f367353e34a82bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 10V, Negative-QTOF	splash10-014i-2090000000-e526de0cd9ea6ea5c67b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 20V, Negative-QTOF	splash10-0006-9010000000-61cd151f31d096cf0b46	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 40V, Negative-QTOF	splash10-0006-9300000000-8a074704ab6b4e05587e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 10V, Positive-QTOF	splash10-014i-0090000000-36fb012770300fb47b89	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 20V, Positive-QTOF	splash10-001i-0910000000-81a35adeb459b9224a95	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 40V, Positive-QTOF	splash10-001i-1900000000-a813694dc7e1cf8740c1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 10V, Negative-QTOF	splash10-014i-0090000000-bd7cd943428e7be367e7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 20V, Negative-QTOF	splash10-0006-9330000000-2c2090cefb411296eb0b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 40V, Negative-QTOF	splash10-0006-9500000000-16f823d8b48ce7469f21	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Phenytoin (Antiarrhythmic) Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	4049465	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.305 (0.522-2.386) uM	Adult (>18 years old)	Female	Epilepsy	2362000	details

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

16756

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17732

PDB ID

Not Available

ChEBI ID

63804

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

Jurgens U: Routine determination of hydroxyphenytoin in urine by high-performance liquid chromatography using an automatic column-switching technique. J Chromatogr. 1983 Jul 8;275(2):335-43. [PubMed:6619238 ]
Sato A, Shimada K, Izumo Y, Sakaguchi T: High-performance liquid chromatographic determination of phenytoin and hydroxyphenytoin in human urine. J Chromatogr. 1983 Jun 10;275(1):97-105. [PubMed:6874875 ]
Zeng J, Liu D, Zou Y: [High performance liquid chromatographic determination of hydroxyphenytoin in human urine]. Hua Xi Yi Ke Da Xue Xue Bao. 1992 Sep;23(3):321-4. [PubMed:1298726 ]
Shimada K, Wakabayashi H, Sato A: Gas chromatographic determination of m- and p-hydroxyphenytoin in the urine of epileptic patients. J Chromatogr. 1985 May 3;339(2):331-7. [PubMed:4008572 ]
Chou RC, Levy G: Effect of pregnancy on the pharmacokinetics of phenytoin in rats. J Pharmacol Exp Ther. 1984 May;229(2):351-8. [PubMed:6716263 ]
Rambeck B, May T: Urinary hydroxyphenytoin/creatinine ratios as an index of compliance in adult epileptic patients on phenytoin therapy. Ther Drug Monit. 1984;6(2):164-72. [PubMed:6740735 ]
Horsmans Y, Van den Berge V, Bouckaert A, Desager JP: Phenytoin hydroxylation in a healthy Caucasian population: bimodal distribution of hydroxyphenytoin urinary excretion. Pharmacol Toxicol. 1997 Dec;81(6):276-9. [PubMed:9444669 ]
Yamanaka H, Nakajima M, Hara Y, Katoh M, Tachibana O, Yamashita J, Yokoi T: Urinary excretion of phenytoin metabolites, 5-(4'-hydroxyphenyl)-5-phenylhydantoin and its O-glucuronide in humans and analysis of genetic polymorphisms of UDP-glucuronosyltransferases. Drug Metab Pharmacokinet. 2005 Apr;20(2):135-43. [PubMed:15855726 ]

Showing metabocard for 4-Hydroxyphenytoin (HMDB0041905)

MOL for HMDB0041905 (4-Hydroxyphenytoin)

3D MOL for HMDB0041905 (4-Hydroxyphenytoin)

3D SDF for HMDB0041905 (4-Hydroxyphenytoin)

3D-SDF for HMDB0041905 (4-Hydroxyphenytoin)

PDB for HMDB0041905 (4-Hydroxyphenytoin)

3D PDB for HMDB0041905 (4-Hydroxyphenytoin)

SMILES for HMDB0041905 (4-Hydroxyphenytoin)

INCHI for HMDB0041905 (4-Hydroxyphenytoin)

Structure for HMDB0041905 (4-Hydroxyphenytoin)

3D Structure for HMDB0041905 (4-Hydroxyphenytoin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra