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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:42 UTC

HMDB ID

HMDB0014673

Secondary Accession Numbers

HMDB14673

Metabolite Identification

Common Name

Mephenytoin

Description

Mephenytoin, also known as mefenitoina or methylphenetoin, belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. Mephenytoin is a drug which is used for the treatment of refractory partial epilepsy. In humans, mephenytoin is involved in the ibuprofen action pathway. Mephenytoin 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 Mephenytoin.

Structure

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

HMDB0257078
     RDKit          3D
R-Mephenytoin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.4112    2.1727    1.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1143    1.6180    1.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003    0.5970    0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0379    0.1129   -0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1403   -0.9994   -1.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3534   -1.4840   -1.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5266   -0.8776   -1.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4680    0.2168   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2289    0.6956    0.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0788    1.0891   -0.8389 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8669    0.0035   -1.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4872   -0.0919   -2.4095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028   -1.0476   -0.3444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -2.3295   -0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1037   -0.5675    0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0364   -1.0094    1.9063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1703    3.1822    2.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774    2.3328    1.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7994    1.5778    2.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4568    2.4640    0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.2084    2.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2134   -1.4801   -1.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4002   -2.3600   -2.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5016   -1.2558   -1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3736    0.6922    0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2235    1.5655    0.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011    2.0400   -1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4140   -2.3030   -1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9857   -2.6361    0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8617   -3.1266   -0.7258 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
  8  9  2  0
  3 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15  3  1  0
  9  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
M  END

532
  Mrv0541 02231214452D          

 16 17  0  0  1  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
  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
M  END
> <DATABASE_ID>
HMDB0014673

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16)

> <INCHI_KEY>
GMHKMTDVRCWUDX-UHFFFAOYSA-N

> <FORMULA>
C12H14N2O2

> <MOLECULAR_WEIGHT>
218.2518

> <EXACT_MASS>
218.105527702

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.666201425874362

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione

> <ALOGPS_LOGP>
1.64

> <JCHEM_LOGP>
1.6651732839999998

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.179447259247729

> <JCHEM_PKA_STRONGEST_BASIC>
-8.139137354400296

> <JCHEM_POLAR_SURFACE_AREA>
49.410000000000004

> <JCHEM_REFRACTIVITY>
59.53800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mephenytoin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257078
     RDKit          3D
R-Mephenytoin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.4112    2.1727    1.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1143    1.6180    1.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003    0.5970    0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0379    0.1129   -0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1403   -0.9994   -1.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3534   -1.4840   -1.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5266   -0.8776   -1.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4680    0.2168   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2289    0.6956    0.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0788    1.0891   -0.8389 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8669    0.0035   -1.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4872   -0.0919   -2.4095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028   -1.0476   -0.3444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -2.3295   -0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1037   -0.5675    0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0364   -1.0094    1.9063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1703    3.1822    2.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774    2.3328    1.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7994    1.5778    2.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4568    2.4640    0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.2084    2.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2134   -1.4801   -1.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4002   -2.3600   -2.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5016   -1.2558   -1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3736    0.6922    0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2235    1.5655    0.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011    2.0400   -1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4140   -2.3030   -1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9857   -2.6361    0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8617   -3.1266   -0.7258 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
  8  9  2  0
  3 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15  3  1  0
  9  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 532                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-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
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                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0257078
HETATM    1  C1  UNL     1      -1.411   2.173   1.883  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.114   1.618   1.344  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.300   0.597   0.281  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.038   0.113  -0.165  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.140  -0.999  -1.007  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.353  -1.484  -1.439  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.527  -0.878  -1.048  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.468   0.217  -0.222  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.229   0.696   0.207  1.00  0.00           C  
HETATM   10  N1  UNL     1      -1.079   1.089  -0.839  1.00  0.00           N  
HETATM   11  C10 UNL     1      -1.867   0.004  -1.303  1.00  0.00           C  
HETATM   12  O1  UNL     1      -2.487  -0.092  -2.409  1.00  0.00           O  
HETATM   13  N2  UNL     1      -1.903  -1.048  -0.344  1.00  0.00           N  
HETATM   14  C11 UNL     1      -2.583  -2.330  -0.406  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.104  -0.568   0.732  1.00  0.00           C  
HETATM   16  O2  UNL     1      -1.036  -1.009   1.906  1.00  0.00           O  
HETATM   17  H1  UNL     1      -1.170   3.182   2.310  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.177   2.333   1.119  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.799   1.578   2.731  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.457   2.464   0.909  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.470   1.208   2.177  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.213  -1.480  -1.318  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.400  -2.360  -2.100  1.00  0.00           H  
HETATM   24  H8  UNL     1       4.502  -1.256  -1.387  1.00  0.00           H  
HETATM   25  H9  UNL     1       4.374   0.692   0.085  1.00  0.00           H  
HETATM   26  H10 UNL     1       2.224   1.565   0.866  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.101   2.040  -1.268  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.414  -2.303  -1.138  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.986  -2.636   0.571  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.862  -3.127  -0.726  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   10   15
CONECT    4    5    5    9
CONECT    5    6   22
CONECT    6    7    7   23
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   26
CONECT   10   11   27
CONECT   11   12   12   13
CONECT   13   14   15
CONECT   14   28   29   30
CONECT   15   16   16
END

HMDB0257078
     RDKit          3D
R-Mephenytoin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.4112    2.1727    1.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1143    1.6180    1.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003    0.5970    0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0379    0.1129   -0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1403   -0.9994   -1.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3534   -1.4840   -1.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5266   -0.8776   -1.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4680    0.2168   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2289    0.6956    0.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0788    1.0891   -0.8389 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8669    0.0035   -1.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4872   -0.0919   -2.4095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028   -1.0476   -0.3444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -2.3295   -0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1037   -0.5675    0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0364   -1.0094    1.9063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1703    3.1822    2.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774    2.3328    1.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7994    1.5778    2.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4568    2.4640    0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.2084    2.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2134   -1.4801   -1.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4002   -2.3600   -2.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5016   -1.2558   -1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3736    0.6922    0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2235    1.5655    0.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011    2.0400   -1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4140   -2.3030   -1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9857   -2.6361    0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8617   -3.1266   -0.7258 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
  8  9  2  0
  3 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15  3  1  0
  9  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
DL-Mephenytoin	ChEBI
Mefenitoina	ChEBI
Mephenytoine	ChEBI
Mephenytoinum	ChEBI
Methylphenetoin	ChEBI
Phenylethylmethylhydantoin	ChEBI
Mesantoin	Kegg
Mephentoin	HMDB
Methyl hydantoin	HMDB
5 Ethyl 3 methyl 5 phenylhydantoin	MeSH, HMDB
5-Ethyl-3-methyl-5-phenylhydantoin	MeSH, HMDB
Phenetoin, methyl	MeSH, HMDB
Methoin	MeSH, HMDB
Methyl phenetoin	MeSH, HMDB
Phenantoin	MeSH, HMDB
Mefenetoin	MeSH, HMDB

Chemical Formula

C₁₂H₁₄N₂O₂

Average Molecular Weight

218.2518

Monoisotopic Molecular Weight

218.105527702

IUPAC Name

5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione

Traditional Name

mephenytoin

CAS Registry Number

50-12-4

SMILES

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

InChI Identifier

InChI=1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16)

InChI Key

GMHKMTDVRCWUDX-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
N-acyl urea
Ureide
Monocyclic benzene moiety
Benzenoid
Dicarboximide
Urea
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
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)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014673)

Source

Exogenous

Exogenous (HMDB: HMDB0014673)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	135 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.97 g/L	Not Available
LogP	1.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.97 g/L	ALOGPS
logP	1.64	ALOGPS
logP	1.67	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	11.18	ChemAxon
pKa (Strongest Basic)	-8.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.41 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	59.54 m³·mol⁻¹	ChemAxon
Polarizability	22.67 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]+	151.303	31661259
DarkChem	[M-H]-	149.616	31661259
DeepCCS	[M+H]+	154.547	30932474
DeepCCS	[M-H]-	152.189	30932474
DeepCCS	[M-2H]-	185.084	30932474
DeepCCS	[M+Na]+	160.64	30932474
AllCCS	[M+H]+	148.2	32859911
AllCCS	[M+H-H2O]+	144.1	32859911
AllCCS	[M+NH4]+	152.1	32859911
AllCCS	[M+Na]+	153.2	32859911
AllCCS	[M-H]-	152.0	32859911
AllCCS	[M+Na-2H]-	152.1	32859911
AllCCS	[M+HCOO]-	152.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mephenytoin	CCC1(NC(=O)N(C)C1=O)C1=CC=CC=C1	2878.0	Standard polar	33892256
Mephenytoin	CCC1(NC(=O)N(C)C1=O)C1=CC=CC=C1	1831.5	Standard non polar	33892256
Mephenytoin	CCC1(NC(=O)N(C)C1=O)C1=CC=CC=C1	1805.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mephenytoin,1TMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C	1868.6	Semi standard non polar	33892256
Mephenytoin,1TMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C	1892.9	Standard non polar	33892256
Mephenytoin,1TMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C	2461.0	Standard polar	33892256
Mephenytoin,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C(C)(C)C	2094.5	Semi standard non polar	33892256
Mephenytoin,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C(C)(C)C	2133.2	Standard non polar	33892256
Mephenytoin,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C(C)(C)C	2531.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Mephenytoin EI-B (Non-derivatized)	splash10-0f79-2900000000-af8712fc36e2b911e9a8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Mephenytoin EI-B (Non-derivatized)	splash10-0f79-2900000000-af8712fc36e2b911e9a8	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mephenytoin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ue9-1900000000-76ba03e4694ef29def3b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mephenytoin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mephenytoin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mephenytoin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mephenytoin LC-ESI-qTof , Positive-QTOF	splash10-0159-3901000000-d726d8591f6fd6b87a0a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mephenytoin , positive-QTOF	splash10-0159-3901000000-d726d8591f6fd6b87a0a	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mephenytoin 10V, Positive-QTOF	splash10-014i-0490000000-8c8bcd12840df6ae00f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mephenytoin 20V, Positive-QTOF	splash10-001i-0920000000-360996524b6c1cdc8fe3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mephenytoin 40V, Positive-QTOF	splash10-0ue9-6900000000-5f6a566d2e8972a3e79c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mephenytoin 10V, Negative-QTOF	splash10-014i-0290000000-de9e2d95bc7cf0aea9ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mephenytoin 20V, Negative-QTOF	splash10-014i-7590000000-9cb9accf3f7737fa1483	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mephenytoin 40V, Negative-QTOF	splash10-000x-9600000000-a00ec47fefbdc60a200a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mephenytoin 10V, Positive-QTOF	splash10-014i-0190000000-8b9cb11606c241146d8b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mephenytoin 20V, Positive-QTOF	splash10-00lr-1900000000-a867b49304e4c2814177	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mephenytoin 40V, Positive-QTOF	splash10-014i-6900000000-2fd710ba16d058127ae9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mephenytoin 10V, Negative-QTOF	splash10-014i-0090000000-4f94e1f66d72d6972b8a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mephenytoin 20V, Negative-QTOF	splash10-000i-2900000000-be298ddea23898cbfbc6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mephenytoin 40V, Negative-QTOF	splash10-01ox-6900000000-8676a25532452b4ac29b	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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 DB00532	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00532	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00532

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3920

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mephenytoin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

6757

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 Mephenytoin (HMDB0014673)

MOL for HMDB0014673 (Mephenytoin)

3D MOL for HMDB0014673 (Mephenytoin)

3D SDF for HMDB0014673 (Mephenytoin)

3D-SDF for HMDB0014673 (Mephenytoin)

PDB for HMDB0014673 (Mephenytoin)

3D PDB for HMDB0014673 (Mephenytoin)

SMILES for HMDB0014673 (Mephenytoin)

INCHI for HMDB0014673 (Mephenytoin)

Structure for HMDB0014673 (Mephenytoin)

3D Structure for HMDB0014673 (Mephenytoin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra