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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:22 UTC

Update Date

2021-09-14 15:44:52 UTC

HMDB ID

HMDB0013894

Secondary Accession Numbers

HMDB13894

Metabolite Identification

Common Name

S-4-Hydroxymephenytoin

Description

S-4-Hydroxymephenytoin is only found in individuals that have used or taken Mephenytoin. S-4-Hydroxymephenytoin is a metabolite of Mephenytoin. S-4-hydroxymephenytoin belongs to the family of Ureides. These are compounds containing an ureide group with the general structure R-CO-NH-CO-N(R)R'', formally derived by the acylation of urea.

Structure

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

HMDB0013894
     RDKit          3D
S-4-Hydroxymephenytoin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -1.0446   -2.6993    0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4470   -1.5225   -0.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8473   -0.2260    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271   -0.2511    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3659   -0.1085   -1.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7471   -0.1322   -1.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4465   -0.3017    0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8418   -0.3300    0.0982 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7293   -0.4453    1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616   -0.4206    1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411    0.1040    1.3835 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967    1.4493    1.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1219    2.1311    2.4300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8296    1.9050    0.0690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2513    3.2619   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4002    0.8645   -0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4772    0.8699   -2.0230 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0365   -2.8286    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4483   -3.6093   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5733   -2.6244    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2057   -1.6395   -1.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5488   -1.4202   -0.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8841    0.0286   -2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425   -0.0215   -2.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2895   -1.2294   -0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2662   -0.5789    2.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8505   -0.5379    2.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3779   -0.5057    2.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138    4.0192   -0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2617    3.4903    0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020    3.3090   -1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16  3  1  0
 10  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END

[NO NAME]
  Mrv0541 09021217532D          
Created with ChemWriter - http://chemwriter.com
 17 18  0  0  0  0            999 V2000
    2.0082    1.2299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9124    1.2299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8728    0.1902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603    1.4598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478    0.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2631   -0.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7929    0.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478   -0.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277    0.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7622   -1.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3333   -1.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603    2.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7622   -1.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3333   -1.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478   -2.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478   -3.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  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  7  1  0  0  0  0
  4  9  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  2  0  0  0  0
  8 12  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013894

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1(NC(=O)N(C)C1=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2O3/c1-3-12(8-4-6-9(15)7-5-8)10(16)14(2)11(17)13-12/h4-7,15H,3H2,1-2H3,(H,13,17)

> <INCHI_KEY>
OQPLORUDZLXXPD-UHFFFAOYSA-N

> <FORMULA>
C12H14N2O3

> <MOLECULAR_WEIGHT>
234.2512

> <EXACT_MASS>
234.100442324

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.675082150044677

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-ethyl-5-(4-hydroxyphenyl)-3-methylimidazolidine-2,4-dione

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
1.3616079623333335

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.477394509045974

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.45556610639133

> <JCHEM_PKA_STRONGEST_BASIC>
-5.959340141164728

> <JCHEM_POLAR_SURFACE_AREA>
69.64

> <JCHEM_REFRACTIVITY>
61.51890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-ethyl-5-(4-hydroxyphenyl)-3-methylimidazolidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013894
     RDKit          3D
S-4-Hydroxymephenytoin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -1.0446   -2.6993    0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4470   -1.5225   -0.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8473   -0.2260    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271   -0.2511    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3659   -0.1085   -1.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7471   -0.1322   -1.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4465   -0.3017    0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8418   -0.3300    0.0982 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7293   -0.4453    1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616   -0.4206    1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411    0.1040    1.3835 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967    1.4493    1.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1219    2.1311    2.4300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8296    1.9050    0.0690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2513    3.2619   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4002    0.8645   -0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4772    0.8699   -2.0230 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0365   -2.8286    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4483   -3.6093   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5733   -2.6244    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2057   -1.6395   -1.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5488   -1.4202   -0.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8841    0.0286   -2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425   -0.0215   -2.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2895   -1.2294   -0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2662   -0.5789    2.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8505   -0.5379    2.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3779   -0.5057    2.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138    4.0192   -0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2617    3.4903    0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020    3.3090   -1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16  3  1  0
 10  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 02-SEP-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-12         0                                  
HETATM    1  O   UNK     0       3.749   2.296   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.170   2.296   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.229   0.355   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       6.459   2.725   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.689   0.355   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.224  -0.121   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.213   1.820   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.689  -1.185   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.705   1.820   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080   0.910   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.023  -1.955   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.355  -1.955   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.459   4.265   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.023  -3.495   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.355  -3.495   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.689  -4.265   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.689  -5.805   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    9                                                            
CONECT    3    5    9                                                       
CONECT    4    7    9   13                                                  
CONECT    5    3    6    7    8                                             
CONECT    6    5   10                                                       
CONECT    7    1    4    5                                                  
CONECT    8    5   11   12                                                  
CONECT    9    2    3    4                                                  
CONECT   10    6                                                            
CONECT   11    8   14                                                       
CONECT   12    8   15                                                       
CONECT   13    4                                                            
CONECT   14   11   16                                                       
CONECT   15   12   16                                                       
CONECT   16   14   15   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0013894
HETATM    1  C1  UNL     1      -1.045  -2.699   0.411  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.447  -1.522  -0.441  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.847  -0.226   0.045  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.627  -0.251   0.045  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.366  -0.109  -1.112  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.747  -0.132  -1.111  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.447  -0.302   0.065  1.00  0.00           C  
HETATM    8  O1  UNL     1       4.842  -0.330   0.098  1.00  0.00           O  
HETATM    9  C8  UNL     1       2.729  -0.445   1.226  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.362  -0.421   1.215  1.00  0.00           C  
HETATM   11  N1  UNL     1      -1.341   0.104   1.384  1.00  0.00           N  
HETATM   12  C10 UNL     1      -1.797   1.449   1.394  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.122   2.131   2.430  1.00  0.00           O  
HETATM   14  N2  UNL     1      -1.830   1.905   0.069  1.00  0.00           N  
HETATM   15  C11 UNL     1      -2.251   3.262  -0.335  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.400   0.864  -0.781  1.00  0.00           C  
HETATM   17  O3  UNL     1      -1.477   0.870  -2.023  1.00  0.00           O  
HETATM   18  H1  UNL     1       0.036  -2.829   0.503  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.448  -3.609  -0.089  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.573  -2.624   1.390  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.206  -1.640  -1.497  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.549  -1.420  -0.350  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.884   0.029  -2.074  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.343  -0.022  -2.012  1.00  0.00           H  
HETATM   25  H8  UNL     1       5.289  -1.229  -0.010  1.00  0.00           H  
HETATM   26  H9  UNL     1       3.266  -0.579   2.154  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.851  -0.538   2.155  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.378  -0.506   2.230  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.514   4.019  -0.006  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.262   3.490   0.064  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.302   3.309  -1.443  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   11   16
CONECT    4    5    5   10
CONECT    5    6   23
CONECT    6    7    7   24
CONECT    7    8    9
CONECT    8   25
CONECT    9   10   10   26
CONECT   10   27
CONECT   11   12   28
CONECT   12   13   13   14
CONECT   14   15   16
CONECT   15   29   30   31
CONECT   16   17   17
END

HMDB0013894
     RDKit          3D
S-4-Hydroxymephenytoin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -1.0446   -2.6993    0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4470   -1.5225   -0.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8473   -0.2260    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271   -0.2511    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3659   -0.1085   -1.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7471   -0.1322   -1.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4465   -0.3017    0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8418   -0.3300    0.0982 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7293   -0.4453    1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616   -0.4206    1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411    0.1040    1.3835 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967    1.4493    1.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1219    2.1311    2.4300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8296    1.9050    0.0690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2513    3.2619   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4002    0.8645   -0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4772    0.8699   -2.0230 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0365   -2.8286    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4483   -3.6093   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5733   -2.6244    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2057   -1.6395   -1.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5488   -1.4202   -0.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8841    0.0286   -2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425   -0.0215   -2.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2895   -1.2294   -0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2662   -0.5789    2.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8505   -0.5379    2.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3779   -0.5057    2.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138    4.0192   -0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2617    3.4903    0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020    3.3090   -1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16  3  1  0
 10  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Hydroxymephenytoin, (S)-isomer	HMDB
Para-hydroxymephenytoin	HMDB
4-Hydroxymephenytoin	HMDB

Chemical Formula

C₁₂H₁₄N₂O₃

Average Molecular Weight

234.2512

Monoisotopic Molecular Weight

234.100442324

IUPAC Name

5-ethyl-5-(4-hydroxyphenyl)-3-methylimidazolidine-2,4-dione

Traditional Name

5-ethyl-5-(4-hydroxyphenyl)-3-methylimidazolidine-2,4-dione

CAS Registry Number

Not Available

SMILES

CCC1(NC(=O)N(C)C1=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C12H14N2O3/c1-3-12(8-4-6-9(15)7-5-8)10(16)14(2)11(17)13-12/h4-7,15H,3H2,1-2H3,(H,13,17)

InChI Key

OQPLORUDZLXXPD-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

5-phenylhydantoin
Phenylimidazolidine
Alpha-amino acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
N-acyl urea
Phenol
Ureide
Monocyclic benzene moiety
Benzenoid
Dicarboximide
Carbonic acid derivative
Urea
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
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: HMDB0013894)
Kidney (HMDB: HMDB0013894)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013894)

Source

Endogenous

Endogenous (HMDB: HMDB0013894)

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	3.71 g/L	ALOGPS
logP	1.08	ALOGPS
logP	1.36	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.64 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.52 m³·mol⁻¹	ChemAxon
Polarizability	23.68 Å³	ChemAxon
Number of Rings	2	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]+	155.327	31661259
DarkChem	[M-H]-	154.263	31661259
DeepCCS	[M+H]+	162.188	30932474
DeepCCS	[M-H]-	159.83	30932474
DeepCCS	[M-2H]-	192.717	30932474
DeepCCS	[M+Na]+	168.282	30932474
AllCCS	[M+H]+	152.4	32859911
AllCCS	[M+H-H2O]+	148.4	32859911
AllCCS	[M+NH4]+	156.1	32859911
AllCCS	[M+Na]+	157.2	32859911
AllCCS	[M-H]-	155.2	32859911
AllCCS	[M+Na-2H]-	155.3	32859911
AllCCS	[M+HCOO]-	155.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-4-Hydroxymephenytoin	CCC1(NC(=O)N(C)C1=O)C1=CC=C(O)C=C1	3405.4	Standard polar	33892256
S-4-Hydroxymephenytoin	CCC1(NC(=O)N(C)C1=O)C1=CC=C(O)C=C1	2200.6	Standard non polar	33892256
S-4-Hydroxymephenytoin	CCC1(NC(=O)N(C)C1=O)C1=CC=C(O)C=C1	2195.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
S-4-Hydroxymephenytoin,1TMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C)C=C2)NC(=O)N(C)C1=O	2280.8	Semi standard non polar	33892256
S-4-Hydroxymephenytoin,1TMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C)C=C2)NC(=O)N(C)C1=O	2280.8	Semi standard non polar	33892256
S-4-Hydroxymephenytoin,1TMS,isomer #2	CCC1(C2=CC=C(O)C=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C	2076.5	Semi standard non polar	33892256
S-4-Hydroxymephenytoin,1TMS,isomer #2	CCC1(C2=CC=C(O)C=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C	2076.5	Semi standard non polar	33892256
S-4-Hydroxymephenytoin,2TMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C	2131.7	Semi standard non polar	33892256
S-4-Hydroxymephenytoin,2TMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C	2172.2	Standard non polar	33892256
S-4-Hydroxymephenytoin,2TMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C	2606.8	Standard polar	33892256
S-4-Hydroxymephenytoin,1TBDMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)NC(=O)N(C)C1=O	2522.6	Semi standard non polar	33892256
S-4-Hydroxymephenytoin,1TBDMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)NC(=O)N(C)C1=O	2522.6	Semi standard non polar	33892256
S-4-Hydroxymephenytoin,1TBDMS,isomer #2	CCC1(C2=CC=C(O)C=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C(C)(C)C	2340.5	Semi standard non polar	33892256
S-4-Hydroxymephenytoin,1TBDMS,isomer #2	CCC1(C2=CC=C(O)C=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C(C)(C)C	2340.5	Semi standard non polar	33892256
S-4-Hydroxymephenytoin,2TBDMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C(C)(C)C	2586.1	Semi standard non polar	33892256
S-4-Hydroxymephenytoin,2TBDMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C(C)(C)C	2660.0	Standard non polar	33892256
S-4-Hydroxymephenytoin,2TBDMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C(C)(C)C	2766.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - S-4-Hydroxymephenytoin GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i1-1920000000-7afcd60942dd73d5a2fe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-4-Hydroxymephenytoin GC-MS (1 TMS) - 70eV, Positive	splash10-0096-2590000000-f2cc0a8f7eec622f615e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-4-Hydroxymephenytoin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-4-Hydroxymephenytoin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-4-Hydroxymephenytoin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-4-Hydroxymephenytoin 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 - S-4-Hydroxymephenytoin 10V, Positive-QTOF	splash10-000i-0390000000-0c74607072d5df473d4e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-4-Hydroxymephenytoin 20V, Positive-QTOF	splash10-0002-0940000000-ecd23b96737a2da30042	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-4-Hydroxymephenytoin 40V, Positive-QTOF	splash10-0002-4900000000-91ee5eff3db1f2867e1b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-4-Hydroxymephenytoin 10V, Negative-QTOF	splash10-001i-0190000000-77b066a7e80bd2325f4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-4-Hydroxymephenytoin 20V, Negative-QTOF	splash10-001l-6290000000-0b31de4400248d9df176	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-4-Hydroxymephenytoin 40V, Negative-QTOF	splash10-0006-9600000000-51ddbfd0c12456ae47e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-4-Hydroxymephenytoin 10V, Negative-QTOF	splash10-001i-0090000000-424acbac5826c17df41d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-4-Hydroxymephenytoin 20V, Negative-QTOF	splash10-0a4i-3890000000-a0fc306b734a76a494be	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-4-Hydroxymephenytoin 40V, Negative-QTOF	splash10-0006-8910000000-d013bc9c9f7dc609fb9f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-4-Hydroxymephenytoin 10V, Positive-QTOF	splash10-000i-0090000000-4c76c6e31a5c811c68e1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-4-Hydroxymephenytoin 20V, Positive-QTOF	splash10-0udi-2910000000-0a9fd68cf0226fe92afb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-4-Hydroxymephenytoin 40V, Positive-QTOF	splash10-0apj-5910000000-0facf710211151a5c8d4	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

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

106722

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119507

PDB ID

Not Available

ChEBI ID

838827

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 S-4-Hydroxymephenytoin (HMDB0013894)

MOL for HMDB0013894 (S-4-Hydroxymephenytoin)

3D MOL for HMDB0013894 (S-4-Hydroxymephenytoin)

3D SDF for HMDB0013894 (S-4-Hydroxymephenytoin)

3D-SDF for HMDB0013894 (S-4-Hydroxymephenytoin)

PDB for HMDB0013894 (S-4-Hydroxymephenytoin)

3D PDB for HMDB0013894 (S-4-Hydroxymephenytoin)

SMILES for HMDB0013894 (S-4-Hydroxymephenytoin)

INCHI for HMDB0013894 (S-4-Hydroxymephenytoin)

Structure for HMDB0013894 (S-4-Hydroxymephenytoin)

3D Structure for HMDB0013894 (S-4-Hydroxymephenytoin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra