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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014397

Secondary Accession Numbers

HMDB14397

Metabolite Identification

Common Name

Phenytoin

Description

An anticonvulsant that is used in a wide variety of seizures. It is also an anti-arrhythmic and a muscle relaxant. The mechanism of therapeutic action is not clear, although several cellular actions have been described including effects on ion channels, active transport, and general membrane stabilization. The mechanism of its muscle relaxant effect appears to involve a reduction in the sensitivity of muscle spindles to stretch. Phenytoin has been proposed for several other therapeutic uses, but its use has been limited by its many adverse effects and interactions with other drugs. [PubChem]

Structure

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

HMDB0014397
     RDKit          3D
Phenytoin
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.7358   -3.9295   -1.1683 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2583   -2.9755   -0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2594   -2.8409    0.9284 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -1.6071    1.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9418   -1.2768    2.2958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2838   -0.8141   -0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0675   -0.1767   -0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445    0.0818    1.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867    0.6720    1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5755    1.0176   -0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9187    0.7698   -1.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6613    0.1713   -1.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3473    0.2261   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859    0.3180   -1.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1609    1.3155   -1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2571    2.1637   -0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4021    2.0450    0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4340    1.0682    0.9823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937   -1.8175   -1.0570 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6589   -3.5147    1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3002   -0.1827    2.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5063    0.8678    2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5703    1.4916   -0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3929    1.0466   -2.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2157    0.0129   -2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211   -0.3419   -2.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8211    1.3745   -2.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0287    2.9360   -0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5144    2.7417    1.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7666    1.0004    1.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029   -1.8430   -1.9864 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  0
  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  2  0
  6 19  1  0
 19  2  1  0
 12  7  1  0
 18 13  1  0
  3 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

1775
  Mrv1652305271900262D          

 19 21  0  0  0  0            999 V2000
    3.5022    1.7788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2311    0.7855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8988    0.1642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9453    1.4983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1235    0.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8414   -0.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2990    0.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1523    1.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4066    0.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1268   -0.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9117    1.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5558   -0.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618   -0.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872    1.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1268   -1.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5558   -1.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0373   -0.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8414   -1.9789    0.0000 C   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  0  0  0  0
  5  7  1  0  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
M  END
> <DATABASE_ID>
HMDB0014397

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12N2O2/c18-13-15(17-14(19)16-13,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,16,17,18,19)

> <INCHI_KEY>
CXOFVDLJLONNDW-UHFFFAOYSA-N

> <FORMULA>
C15H12N2O2

> <MOLECULAR_WEIGHT>
252.268

> <EXACT_MASS>
252.089877638

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
25.481526782247503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,5-diphenylimidazolidine-2,4-dione

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.1479203806666667

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.280494598437553

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.486301952880222

> <JCHEM_PKA_STRONGEST_BASIC>
-9.048670716437814

> <JCHEM_POLAR_SURFACE_AREA>
58.2

> <JCHEM_REFRACTIVITY>
70.18230000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
silantin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014397
     RDKit          3D
Phenytoin
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.7358   -3.9295   -1.1683 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2583   -2.9755   -0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2594   -2.8409    0.9284 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -1.6071    1.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9418   -1.2768    2.2958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2838   -0.8141   -0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0675   -0.1767   -0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445    0.0818    1.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867    0.6720    1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5755    1.0176   -0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9187    0.7698   -1.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6613    0.1713   -1.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3473    0.2261   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859    0.3180   -1.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1609    1.3155   -1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2571    2.1637   -0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4021    2.0450    0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4340    1.0682    0.9823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937   -1.8175   -1.0570 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6589   -3.5147    1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3002   -0.1827    2.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5063    0.8678    2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5703    1.4916   -0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3929    1.0466   -2.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2157    0.0129   -2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211   -0.3419   -2.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8211    1.3745   -2.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0287    2.9360   -0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5144    2.7417    1.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7666    1.0004    1.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029   -1.8430   -1.9864 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  0
  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  2  0
  6 19  1  0
 19  2  1  0
 12  7  1  0
 18 13  1  0
  3 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1775                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       6.537   3.320   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.631   1.466   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       9.144   0.307   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       9.231   2.797   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.697   0.833   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.171  -0.614   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.158   0.887   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.751   2.372   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.092   1.520   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.837  -1.384   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.435   2.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.504  -1.384   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.342  -0.419   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.896   2.300   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.837  -2.924   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.504  -2.924   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.803  -0.365   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080   0.994   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.171  -3.694   0.000  0.00  0.00           C+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                                                       
CONECT   17   13   18                                                       
CONECT   18   14   17                                                       
CONECT   19   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0014397
HETATM    1  O1  UNL     1       0.736  -3.930  -1.168  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.258  -2.975  -0.487  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.259  -2.841   0.928  1.00  0.00           N  
HETATM    4  C2  UNL     1      -0.390  -1.607   1.197  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.942  -1.277   2.296  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.284  -0.814  -0.057  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.067  -0.177  -0.026  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.744   0.082   1.147  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.987   0.672   1.179  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.575   1.018  -0.010  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.919   0.770  -1.202  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.661   0.171  -1.215  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.347   0.226  -0.100  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.186   0.318  -1.182  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.161   1.315  -1.164  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.257   2.164  -0.087  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.402   2.045   0.981  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.434   1.068   0.982  1.00  0.00           C  
HETATM   19  N2  UNL     1      -0.394  -1.817  -1.057  1.00  0.00           N  
HETATM   20  H1  UNL     1       0.659  -3.515   1.640  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.300  -0.183   2.085  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.506   0.868   2.128  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.570   1.492  -0.005  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.393   1.047  -2.128  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.216   0.013  -2.188  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.121  -0.342  -2.036  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.821   1.375  -2.035  1.00  0.00           H  
HETATM   28  H9  UNL     1      -4.029   2.936  -0.097  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.514   2.742   1.817  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.767   1.000   1.847  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.803  -1.843  -1.986  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4   20
CONECT    4    5    5    6
CONECT    6    7   13   19
CONECT    7    8    8   12
CONECT    8    9   21
CONECT    9   10   10   22
CONECT   10   11   23
CONECT   11   12   12   24
CONECT   12   25
CONECT   13   14   14   18
CONECT   14   15   26
CONECT   15   16   16   27
CONECT   16   17   28
CONECT   17   18   18   29
CONECT   18   30
CONECT   19   31
END

HMDB0014397
     RDKit          3D
Phenytoin
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.7358   -3.9295   -1.1683 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2583   -2.9755   -0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2594   -2.8409    0.9284 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -1.6071    1.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9418   -1.2768    2.2958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2838   -0.8141   -0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0675   -0.1767   -0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445    0.0818    1.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867    0.6720    1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5755    1.0176   -0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9187    0.7698   -1.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6613    0.1713   -1.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3473    0.2261   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859    0.3180   -1.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1609    1.3155   -1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2571    2.1637   -0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4021    2.0450    0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4340    1.0682    0.9823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937   -1.8175   -1.0570 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6589   -3.5147    1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3002   -0.1827    2.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5063    0.8678    2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5703    1.4916   -0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3929    1.0466   -2.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2157    0.0129   -2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211   -0.3419   -2.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8211    1.3745   -2.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0287    2.9360   -0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5144    2.7417    1.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7666    1.0004    1.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029   -1.8430   -1.9864 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  0
  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  2  0
  6 19  1  0
 19  2  1  0
 12  7  1  0
 18 13  1  0
  3 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,5-Diphenyl-imidazolidine-2,4-dione	ChEBI
5,5-Diphenylimidazolidine-2,4-dione	ChEBI
5,5-Diphenyltetrahydro-1H-2,4-imidazoledione	ChEBI
DILANTIN	ChEBI
Fenitoina	ChEBI
PHENTYTOIN	ChEBI
Phenytoine	ChEBI
Phenytoinum	ChEBI
5,5-Diphenylhydantoin	HMDB
5,5-Dwufenylohydantoina	HMDB
Dihydantoin	HMDB
Diphenylan sodium	HMDB
Diphenylhydantoin	HMDB
Diphenylhydatanoin	HMDB
Phenytoin sodium	HMDB
Difenin	HMDB
Diphenylhydantoinate, sodium	HMDB
Park davis brand OF phenytoin	HMDB
Pfizer brand OF phenytoin	HMDB
Sodium diphenylhydantoinate	HMDB
Dihydan	HMDB
Epamin	HMDB
Phenytoin pfizer brand	HMDB
Antisacer	HMDB
Epanutin	HMDB
Hydantol	HMDB
Phenytoin phizer brand	HMDB
Fenitoin	HMDB
Phizer brand OF phenytoin	HMDB

Chemical Formula

C₁₅H₁₂N₂O₂

Average Molecular Weight

252.268

Monoisotopic Molecular Weight

252.089877638

IUPAC Name

5,5-diphenylimidazolidine-2,4-dione

Traditional Name

silantin

CAS Registry Number

57-41-0

SMILES

O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H12N2O2/c18-13-15(17-14(19)16-13,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,16,17,18,19)

InChI Key

CXOFVDLJLONNDW-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
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 oxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazolidine-2,4-dione (CHEBI:8107 )

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

Source

Exogenous

Exogenous (HMDB: HMDB0014397)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Fosphenytoin (Antiarrhythmic) Action Pathway (PathBank: SMP0000326)
Phenytoin (Antiarrhythmic) Action Pathway (PathBank: SMP0000327)

Metabolic pathway

Fosphenytoin (Antiarrhythmic) Metabolism Pathway (PathBank: SMP0000618)

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Anticonvulsant (HMDB: HMDB0014397)

Biological role

Teratogenic agent (HMDB: HMDB0014397)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	286 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.071 g/L	Not Available
LogP	2.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	158.381	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000953

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.071 g/L	ALOGPS
logP	2.26	ALOGPS
logP	2.15	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.18 m³·mol⁻¹	ChemAxon
Polarizability	25.48 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]+	158.475	31661259
DarkChem	[M-H]-	156.599	31661259
DeepCCS	[M+H]+	155.079	30932474
DeepCCS	[M-H]-	152.721	30932474
DeepCCS	[M-2H]-	185.606	30932474
DeepCCS	[M+Na]+	161.172	30932474
AllCCS	[M+H]+	157.6	32859911
AllCCS	[M+H-H2O]+	153.5	32859911
AllCCS	[M+NH4]+	161.3	32859911
AllCCS	[M+Na]+	162.4	32859911
AllCCS	[M-H]-	159.5	32859911
AllCCS	[M+Na-2H]-	158.8	32859911
AllCCS	[M+HCOO]-	158.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenytoin	O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC=CC=C1	3545.4	Standard polar	33892256
Phenytoin	O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC=CC=C1	2415.1	Standard non polar	33892256
Phenytoin	O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC=CC=C1	2380.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenytoin,1TMS,isomer #1	C[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2374.4	Semi standard non polar	33892256
Phenytoin,1TMS,isomer #1	C[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2298.6	Standard non polar	33892256
Phenytoin,1TMS,isomer #1	C[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	3348.5	Standard polar	33892256
Phenytoin,1TMS,isomer #2	C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=CC=C1	2407.6	Semi standard non polar	33892256
Phenytoin,1TMS,isomer #2	C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=CC=C1	2347.5	Standard non polar	33892256
Phenytoin,1TMS,isomer #2	C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=CC=C1	3555.9	Standard polar	33892256
Phenytoin,2TMS,isomer #1	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2163.8	Semi standard non polar	33892256
Phenytoin,2TMS,isomer #1	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2332.8	Standard non polar	33892256
Phenytoin,2TMS,isomer #1	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2948.4	Standard polar	33892256
Phenytoin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2684.1	Semi standard non polar	33892256
Phenytoin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2509.6	Standard non polar	33892256
Phenytoin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	3377.5	Standard polar	33892256
Phenytoin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=CC=C1	2655.2	Semi standard non polar	33892256
Phenytoin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=CC=C1	2539.5	Standard non polar	33892256
Phenytoin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=CC=C1	3524.0	Standard polar	33892256
Phenytoin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2665.4	Semi standard non polar	33892256
Phenytoin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2746.6	Standard non polar	33892256
Phenytoin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	3008.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Phenytoin EI-B (Non-derivatized)	splash10-003r-7930000000-447969b9c242748dd943	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenytoin CI-B (Non-derivatized)	splash10-0udi-0090000000-4176043a7a73caee2667	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenytoin EI-B (Non-derivatized)	splash10-0zgi-5960000000-e1dcb47a1c082f04f456	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenytoin CI-B (Non-derivatized)	splash10-0udi-1390000000-22c71a7e4dbf9c7acab5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenytoin CI-B (Non-derivatized)	splash10-0udi-2190000000-50174e33af92b04d1a6e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenytoin EI-B (Non-derivatized)	splash10-003r-7930000000-447969b9c242748dd943	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenytoin CI-B (Non-derivatized)	splash10-0udi-0090000000-4176043a7a73caee2667	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenytoin EI-B (Non-derivatized)	splash10-0zgi-5960000000-e1dcb47a1c082f04f456	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenytoin CI-B (Non-derivatized)	splash10-0udi-1390000000-22c71a7e4dbf9c7acab5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenytoin CI-B (Non-derivatized)	splash10-0udi-2190000000-50174e33af92b04d1a6e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-0920000000-edf72a4c297e405a2600	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f89-4940000000-2a0dda513d9f63dc6610	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin LC-ESI-qTof , Positive-QTOF	splash10-001i-0950000000-a80521d4dc3976a29b2c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin LC-ESI-qTof , Positive-QTOF	splash10-0ue9-2900000000-a58471ae75fa7319c03d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , negative-QTOF	splash10-0udi-0090000000-aaae845342f345f89695	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , negative-QTOF	splash10-0udi-0390000000-f8da1896c569c120faa2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , negative-QTOF	splash10-0udi-0920000000-07c872b05aade63c402b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , negative-QTOF	splash10-0udi-0900000000-be6790637be99260525e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , negative-QTOF	splash10-0udi-0900000000-9a17fa0b243c8282f3ba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , negative-QTOF	splash10-0udi-0900000000-69302626996b2b24c153	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , positive-QTOF	splash10-0fai-0690000000-f9eeceb82d117127f6ea	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , positive-QTOF	splash10-001i-0910000000-9edcfc62014a6aa7778f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , positive-QTOF	splash10-001i-0900000000-d4dde5db680fb7722a49	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , positive-QTOF	splash10-0ue9-0900000000-482874b33812389ae726	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , positive-QTOF	splash10-0udi-0900000000-44f07dc29daf8cdf80c2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , positive-QTOF	splash10-0udi-1900000000-1241292d531ed37544c7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin , positive-QTOF	splash10-001i-0950000000-a80521d4dc3976a29b2c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin , positive-QTOF	splash10-0ue9-2900000000-a58471ae75fa7319c03d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin 45V, Negative-QTOF	splash10-0udi-0920000000-97a0af331da9afcf54b8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin 60V, Negative-QTOF	splash10-0udi-0900000000-9918b159c9e50b11016f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenytoin 90V, Negative-QTOF	splash10-0udi-0900000000-c2ba734800c5db1b68cf	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin 10V, Positive-QTOF	splash10-0udi-0290000000-168825c4263cc790be0b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin 20V, Positive-QTOF	splash10-0f89-0950000000-27e345a92f7734114654	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin 40V, Positive-QTOF	splash10-0uyi-1900000000-5828317e8dac2d03e548	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin 10V, Negative-QTOF	splash10-0udi-0090000000-e1551530faa59a549515	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin 20V, Negative-QTOF	splash10-0udi-1190000000-354c210fa308dab349f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin 40V, Negative-QTOF	splash10-0006-9700000000-d5833bfc084997249fe4	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

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

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 DB00252	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00252	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00252

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1710

KEGG Compound ID

C07443

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenytoin

METLIN ID

Not Available

PubChem Compound

1775

PDB ID

Not Available

ChEBI ID

8107

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

PharmGKB [Link]

Showing metabocard for Phenytoin (HMDB0014397)

MOL for HMDB0014397 (Phenytoin)

3D MOL for HMDB0014397 (Phenytoin)

3D SDF for HMDB0014397 (Phenytoin)

3D-SDF for HMDB0014397 (Phenytoin)

PDB for HMDB0014397 (Phenytoin)

3D PDB for HMDB0014397 (Phenytoin)

SMILES for HMDB0014397 (Phenytoin)

INCHI for HMDB0014397 (Phenytoin)

Structure for HMDB0014397 (Phenytoin)

3D Structure for HMDB0014397 (Phenytoin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra