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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:23 UTC

Update Date

2021-09-14 15:47:38 UTC

HMDB ID

HMDB0013896

Secondary Accession Numbers

HMDB13896

Metabolite Identification

Common Name

3'-HPPH

Description

3'-HPPH, also called (5R)-5-(3-hydroxyphenyl)-5-phenylimidazolidine-2,4-dione or 3’-hydroxyphenytoin, is a metabolite of Phenytoin. Phenytoin is an anticonvulsant used to treat epilepsy. 3'-HPPH belongs to the family of compounds known as Diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. 3'-HPPH or 3’-hydroxyphenytoin is only found in individuals that have used or taken Phenytoin.

Structure

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

HMDB0013896
     RDKit          3D
3'-HPPH
 32 34  0  0  0  0  0  0  0  0999 V2000
    0.6934    3.3737   -2.7533 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6802    2.7106   -1.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7662    3.1570   -0.3383 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7100    2.0496    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950    2.1140    1.7743 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3956    0.8557   -0.2771 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2957   -0.2763    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973   -0.6810    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138   -1.7190    1.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9222   -2.3667    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052   -1.9524   -0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844   -0.8966   -0.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9806    0.4063    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7498    1.0499    0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0378    0.5513    1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4812   -0.5327    0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7094   -1.1944   -0.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2444   -2.2921   -1.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4482   -0.7078   -0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658    1.2809   -1.6285 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8590    4.1733   -0.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664   -0.1846    2.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1443   -2.0680    2.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597   -3.1808    1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5183   -2.4147   -1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770   -0.5784   -1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3994    1.9185    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6250    1.0793    1.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874   -0.9114    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7587   -2.2017   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8264   -1.2161   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991    0.6547   -2.4596 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  2  0
  4  6  1  0
  6  7  1  1
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
  6 20  1  0
 20  2  1  0
 12  7  1  0
 19 13  1  0
  3 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END

  Mrv0541 06191310282D          

 20 22  0  0  1  0            999 V2000
    8.2793   -1.9437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0083   -2.9370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6760   -3.5583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7225   -2.2242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9006   -3.2762    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6185   -4.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0761   -3.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9294   -2.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1838   -2.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9039   -4.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6888   -2.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3330   -4.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6389   -3.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8643   -2.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9039   -5.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3330   -5.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8144   -3.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4271   -3.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6185   -5.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0474   -5.7015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  2  0  0  0  0
  2  9  2  0  0  0  0
  3  5  1  0  0  0  0
  3  9  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  1  0  0  0
  5  8  1  0  0  0  0
  6 10  2  0  0  0  0
  6 12  1  0  0  0  0
  7 11  2  0  0  0  0
  7 13  1  0  0  0  0
 10 15  1  0  0  0  0
 11 14  1  0  0  0  0
 12 16  2  0  0  0  0
 13 17  2  0  0  0  0
 14 18  2  0  0  0  0
 15 19  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 16 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013896

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(=CC=C1)[C@]1(NC(=O)NC1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12N2O3/c18-12-8-4-7-11(9-12)15(10-5-2-1-3-6-10)13(19)16-14(20)17-15/h1-9,18H,(H2,16,17,19,20)/t15-/m1/s1

> <INCHI_KEY>
FSPRLRPJSPWQNC-OAHLLOKOSA-N

> <FORMULA>
C15H12N2O3

> <MOLECULAR_WEIGHT>
268.2674

> <EXACT_MASS>
268.08479226

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.374969651131806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-5-(3-hydroxyphenyl)-5-phenylimidazolidine-2,4-dione

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.8443550589999997

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.724788447641673

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.094726185691389

> <JCHEM_PKA_STRONGEST_BASIC>
-5.971229181091332

> <JCHEM_POLAR_SURFACE_AREA>
78.43

> <JCHEM_REFRACTIVITY>
72.16320000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-5-(3-hydroxyphenyl)-5-phenylimidazolidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013896
     RDKit          3D
3'-HPPH
 32 34  0  0  0  0  0  0  0  0999 V2000
    0.6934    3.3737   -2.7533 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6802    2.7106   -1.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7662    3.1570   -0.3383 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7100    2.0496    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950    2.1140    1.7743 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3956    0.8557   -0.2771 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2957   -0.2763    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973   -0.6810    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138   -1.7190    1.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9222   -2.3667    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052   -1.9524   -0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844   -0.8966   -0.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9806    0.4063    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7498    1.0499    0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0378    0.5513    1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4812   -0.5327    0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7094   -1.1944   -0.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2444   -2.2921   -1.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4482   -0.7078   -0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658    1.2809   -1.6285 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8590    4.1733   -0.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664   -0.1846    2.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1443   -2.0680    2.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597   -3.1808    1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5183   -2.4147   -1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770   -0.5784   -1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3994    1.9185    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6250    1.0793    1.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874   -0.9114    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7587   -2.2017   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8264   -1.2161   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991    0.6547   -2.4596 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  2  0
  4  6  1  0
  6  7  1  1
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
  6 20  1  0
 20  2  1  0
 12  7  1  0
 19 13  1  0
  3 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END

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  O   UNK     0      15.455  -3.628   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      20.549  -5.482   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      18.062  -6.642   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      18.149  -4.152   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      16.614  -6.116   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.088  -7.563   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.075  -6.062   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.668  -4.577   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.010  -5.429   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.754  -8.333   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.352  -4.702   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.422  -8.333   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.259  -7.368   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.813  -4.648   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.754  -9.873   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.422  -9.873   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.720  -7.314   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.997  -5.954   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.088 -10.643   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.755 -10.643   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    5    9                                                       
CONECT    4    8    9                                                       
CONECT    5    3    6    7    8                                             
CONECT    6    5   10   12                                                  
CONECT    7    5   11   13                                                  
CONECT    8    1    4    5                                                  
CONECT    9    2    3    4                                                  
CONECT   10    6   15                                                       
CONECT   11    7   14                                                       
CONECT   12    6   16                                                       
CONECT   13    7   17                                                       
CONECT   14   11   18                                                       
CONECT   15   10   19                                                       
CONECT   16   12   19   20                                                  
CONECT   17   13   18                                                       
CONECT   18   14   17                                                       
CONECT   19   15   16                                                       
CONECT   20   16                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0013896
HETATM    1  O1  UNL     1       0.693   3.374  -2.753  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.680   2.711  -1.669  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.766   3.157  -0.338  1.00  0.00           N  
HETATM    4  C2  UNL     1       0.710   2.050   0.551  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.895   2.114   1.774  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.396   0.856  -0.277  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.296  -0.276   0.074  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.297  -0.681   1.408  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.114  -1.719   1.771  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.922  -2.367   0.873  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.905  -1.952  -0.435  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.084  -0.897  -0.840  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.981   0.406   0.023  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.750   1.050   0.945  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.038   0.551   1.163  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.481  -0.533   0.471  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.709  -1.194  -0.467  1.00  0.00           C  
HETATM   18  O3  UNL     1      -3.244  -2.292  -1.125  1.00  0.00           O  
HETATM   19  C15 UNL     1      -1.448  -0.708  -0.682  1.00  0.00           C  
HETATM   20  N2  UNL     1       0.566   1.281  -1.629  1.00  0.00           N  
HETATM   21  H1  UNL     1       0.859   4.173  -0.059  1.00  0.00           H  
HETATM   22  H2  UNL     1       0.666  -0.185   2.139  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.144  -2.068   2.813  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.560  -3.181   1.169  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.518  -2.415  -1.211  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.077  -0.578  -1.861  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.399   1.919   1.500  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.625   1.079   1.898  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.487  -0.911   0.650  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.759  -2.202  -1.999  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.826  -1.216  -1.418  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.599   0.655  -2.460  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4   21
CONECT    4    5    5    6
CONECT    6    7   13   20
CONECT    7    8    8   12
CONECT    8    9   22
CONECT    9   10   10   23
CONECT   10   11   24
CONECT   11   12   12   25
CONECT   12   26
CONECT   13   14   14   19
CONECT   14   15   27
CONECT   15   16   16   28
CONECT   16   17   29
CONECT   17   18   19   19
CONECT   18   30
CONECT   19   31
CONECT   20   32
END

HMDB0013896
     RDKit          3D
3'-HPPH
 32 34  0  0  0  0  0  0  0  0999 V2000
    0.6934    3.3737   -2.7533 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6802    2.7106   -1.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7662    3.1570   -0.3383 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7100    2.0496    0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950    2.1140    1.7743 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3956    0.8557   -0.2771 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2957   -0.2763    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973   -0.6810    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138   -1.7190    1.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9222   -2.3667    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052   -1.9524   -0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844   -0.8966   -0.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9806    0.4063    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7498    1.0499    0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0378    0.5513    1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4812   -0.5327    0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7094   -1.1944   -0.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2444   -2.2921   -1.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4482   -0.7078   -0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658    1.2809   -1.6285 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8590    4.1733   -0.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664   -0.1846    2.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1443   -2.0680    2.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597   -3.1808    1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5183   -2.4147   -1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770   -0.5784   -1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3994    1.9185    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6250    1.0793    1.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874   -0.9114    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7587   -2.2017   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8264   -1.2161   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991    0.6547   -2.4596 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  2  0
  4  6  1  0
  6  7  1  1
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
  6 20  1  0
 20  2  1  0
 12  7  1  0
 19 13  1  0
  3 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂N₂O₃

Average Molecular Weight

268.2674

Monoisotopic Molecular Weight

268.08479226

IUPAC Name

(5R)-5-(3-hydroxyphenyl)-5-phenylimidazolidine-2,4-dione

Traditional Name

(5R)-5-(3-hydroxyphenyl)-5-phenylimidazolidine-2,4-dione

CAS Registry Number

Not Available

SMILES

OC1=CC(=CC=C1)[C@]1(NC(=O)NC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H12N2O3/c18-12-8-4-7-11(9-12)15(10-5-2-1-3-6-10)13(19)16-14(20)17-15/h1-9,18H,(H2,16,17,19,20)/t15-/m1/s1

InChI Key

FSPRLRPJSPWQNC-OAHLLOKOSA-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
1-hydroxy-4-unsubstituted benzenoid
Ureide
Monocyclic benzene moiety
Benzenoid
Dicarboximide
Urea
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0013896)
Kidney (HMDB: HMDB0013896)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013896)

Source

Endogenous

Endogenous (HMDB: HMDB0013896)

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	0.13 g/L	ALOGPS
logP	1.67	ALOGPS
logP	1.84	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.09	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.43 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72.16 m³·mol⁻¹	ChemAxon
Polarizability	26.37 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]+	160.862	31661259
DarkChem	[M-H]-	160.155	31661259
DeepCCS	[M+H]+	164.859	30932474
DeepCCS	[M-H]-	162.501	30932474
DeepCCS	[M-2H]-	195.797	30932474
DeepCCS	[M+Na]+	171.024	30932474
AllCCS	[M+H]+	161.0	32859911
AllCCS	[M+H-H2O]+	157.1	32859911
AllCCS	[M+NH4]+	164.6	32859911
AllCCS	[M+Na]+	165.6	32859911
AllCCS	[M-H]-	162.6	32859911
AllCCS	[M+Na-2H]-	162.0	32859911
AllCCS	[M+HCOO]-	161.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3'-HPPH	OC1=CC(=CC=C1)[C@]1(NC(=O)NC1=O)C1=CC=CC=C1	3962.3	Standard polar	33892256
3'-HPPH	OC1=CC(=CC=C1)[C@]1(NC(=O)NC1=O)C1=CC=CC=C1	2751.0	Standard non polar	33892256
3'-HPPH	OC1=CC(=CC=C1)[C@]1(NC(=O)NC1=O)C1=CC=CC=C1	2733.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3'-HPPH,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)NC2=O)=C1	2742.6	Semi standard non polar	33892256
3'-HPPH,1TMS,isomer #2	C[Si](C)(C)N1C(=O)NC(=O)[C@@]1(C1=CC=CC=C1)C1=CC=CC(O)=C1	2614.1	Semi standard non polar	33892256
3'-HPPH,1TMS,isomer #3	C[Si](C)(C)N1C(=O)N[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O	2584.9	Semi standard non polar	33892256
3'-HPPH,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)=C1	2636.8	Semi standard non polar	33892256
3'-HPPH,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)=C1	2580.8	Standard non polar	33892256
3'-HPPH,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)=C1	3697.6	Standard polar	33892256
3'-HPPH,2TMS,isomer #2	C[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)=C1	2688.8	Semi standard non polar	33892256
3'-HPPH,2TMS,isomer #2	C[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)=C1	2527.4	Standard non polar	33892256
3'-HPPH,2TMS,isomer #2	C[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)=C1	3499.4	Standard polar	33892256
3'-HPPH,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O	2333.5	Semi standard non polar	33892256
3'-HPPH,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O	2543.1	Standard non polar	33892256
3'-HPPH,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O	3223.5	Standard polar	33892256
3'-HPPH,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=C1	2422.8	Semi standard non polar	33892256
3'-HPPH,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=C1	2536.5	Standard non polar	33892256
3'-HPPH,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=C1	2993.1	Standard polar	33892256
3'-HPPH,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)NC2=O)=C1	3005.8	Semi standard non polar	33892256
3'-HPPH,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)[C@@]1(C1=CC=CC=C1)C1=CC=CC(O)=C1	2901.2	Semi standard non polar	33892256
3'-HPPH,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O	2927.1	Semi standard non polar	33892256
3'-HPPH,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)=C1	3143.9	Semi standard non polar	33892256
3'-HPPH,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)=C1	2964.3	Standard non polar	33892256
3'-HPPH,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)=C1	3688.3	Standard polar	33892256
3'-HPPH,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)=C1	3205.7	Semi standard non polar	33892256
3'-HPPH,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)=C1	2955.6	Standard non polar	33892256
3'-HPPH,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)=C1	3596.9	Standard polar	33892256
3'-HPPH,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O	2903.5	Semi standard non polar	33892256
3'-HPPH,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O	2963.3	Standard non polar	33892256
3'-HPPH,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O	3276.2	Standard polar	33892256
3'-HPPH,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=C1	3154.7	Semi standard non polar	33892256
3'-HPPH,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=C1	3155.1	Standard non polar	33892256
3'-HPPH,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=C1	3160.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3'-HPPH GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fha-1910000000-07256907a664e226b29e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3'-HPPH GC-MS (1 TMS) - 70eV, Positive	splash10-004i-2981000000-45e106686ee5bd86f810	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3'-HPPH GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3'-HPPH 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 - 3'-HPPH 10V, Positive-QTOF	splash10-014i-0290000000-84e48a5cbdf2651a2354	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-HPPH 20V, Positive-QTOF	splash10-00kb-0960000000-c6b7c6e260986561fee2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-HPPH 40V, Positive-QTOF	splash10-0fdk-2900000000-9b697694cd4ed14b3402	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-HPPH 10V, Negative-QTOF	splash10-014i-0090000000-985e5e440b324877f65b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-HPPH 20V, Negative-QTOF	splash10-014i-2190000000-94e8800e1b1868b448cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-HPPH 40V, Negative-QTOF	splash10-0006-8910000000-1f968e3f670dfcbab35f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-HPPH 10V, Negative-QTOF	splash10-014i-0090000000-bd7cd943428e7be367e7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-HPPH 20V, Negative-QTOF	splash10-00ke-5950000000-844d1044e0dfb175ac75	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-HPPH 40V, Negative-QTOF	splash10-0006-9500000000-3b3f6334c7bef7993d73	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-HPPH 10V, Positive-QTOF	splash10-014i-0190000000-1b299a4a0e6a46c0bb5b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-HPPH 20V, Positive-QTOF	splash10-0002-0920000000-26fb64530d09354a7ea4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-HPPH 40V, Positive-QTOF	splash10-0fmj-5910000000-dcb3a5106906c7151aac	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

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	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	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

628070

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

719586

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 3'-HPPH (HMDB0013896)

MOL for HMDB0013896 (3'-HPPH)

3D MOL for HMDB0013896 (3'-HPPH)

3D SDF for HMDB0013896 (3'-HPPH)

3D-SDF for HMDB0013896 (3'-HPPH)

PDB for HMDB0013896 (3'-HPPH)

3D PDB for HMDB0013896 (3'-HPPH)

SMILES for HMDB0013896 (3'-HPPH)

INCHI for HMDB0013896 (3'-HPPH)

Structure for HMDB0013896 (3'-HPPH)

3D Structure for HMDB0013896 (3'-HPPH)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra