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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:04:24 UTC

Update Date

2021-09-14 15:41:21 UTC

HMDB ID

HMDB0060866

Secondary Accession Numbers

HMDB60866

Metabolite Identification

Common Name

Phenytoin dihydrodiol

Description

Phenytoin dihydrodiol, also known as 5-DCYPH, belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. Phenytoin acts to suppress the abnormal brain activity seen in seizure by reducing electrical conductance among brain cells by stabilizing the inactive state of voltage-gated sodium channels. Phenytoin sodium is a commonly used antiepileptic. Phenytoin dihydrodiol is a metabolite of phenytoin. Phenytoin dihydrodiol is an extremely weak basic (essentially neutral) compound (based on its pKa). phenytoin dihydrodiol can be biosynthesized from phenytoin arene-oxide through its interaction with the enzymes cytochrome P450 1A2, cytochrome P450 2C19, cytochrome P450 2E1, and epoxide hydrolase 1. In humans, phenytoin dihydrodiol is involved in the metabolic disorder called the phenytoin (antiarrhythmic) action pathway. It is sometimes considered a class 1b antiarrhythmic. Aside from seizures, it is an option in the treatment of trigeminal neuralgia in the event that carbamazepine or other first-line treatment seems inappropriate.

Structure

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

HMDB0060866
     RDKit          3D
Phenytoin dihydrodiol
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.3464   -2.0467    3.4366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006   -1.8490    2.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -2.7823    1.1324 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0159   -2.1177   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0849   -2.7046   -1.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7224   -0.6951    0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6699   -0.3319   -0.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628   -0.0002    0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8674    0.3807    0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6054   -0.5401    1.5855 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4213    0.3922   -0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9418    1.6880   -0.8098 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5009    0.0150   -1.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550   -0.3102   -1.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6947    0.2125   -0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2821    1.3482   -1.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146    2.1689   -1.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5489    1.8639   -1.7712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9520    0.7204   -1.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0254   -0.1052   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9720   -0.5922    1.6185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -3.8159    1.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0490   -0.0086    1.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728    1.3837    1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9966   -0.1185    2.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3439   -0.2668   -0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8682    1.7686   -0.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8816    0.0110   -2.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952   -0.5847   -2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2540    1.6243   -1.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9102    3.0696   -2.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3182    2.4547   -2.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9790    0.4255   -1.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3266   -1.0009    0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725    0.3433    2.1173 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  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21  2  1  0
 14  7  1  0
 20 15  1  0
  3 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END

  Mrv0541 07041312042D          

 21 23  0  0  0  0            999 V2000
   -1.0241    1.3951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4720    0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3349    0.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870    0.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6320   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1749   -0.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7270   -0.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340   -0.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1841   -1.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8515   -1.5422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -2.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815   -2.9942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7716   -2.3268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5166   -1.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2680   -1.2872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7361   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4812    0.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0332    0.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8402    0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0951   -0.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5431   -0.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060866

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C=CC(=CC1O)C1(NC(=O)NC1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14N2O4/c18-11-7-6-10(8-12(11)19)15(9-4-2-1-3-5-9)13(20)16-14(21)17-15/h1-8,11-12,18-19H,(H2,16,17,20,21)

> <INCHI_KEY>
FEEKFEKCXIDMIS-UHFFFAOYSA-N

> <FORMULA>
C15H14N2O4

> <MOLECULAR_WEIGHT>
286.2827

> <EXACT_MASS>
286.095356946

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.785174979032224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(3,4-dihydroxycyclohexa-1,5-dien-1-yl)-5-phenylimidazolidine-2,4-dione

> <ALOGPS_LOGP>
0.02

> <JCHEM_LOGP>
-0.162904485

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.45285154466671

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.459856542933796

> <JCHEM_PKA_STRONGEST_BASIC>
-3.340199474843989

> <JCHEM_POLAR_SURFACE_AREA>
98.66

> <JCHEM_REFRACTIVITY>
75.72630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(3,4-dihydroxycyclohexa-1,5-dien-1-yl)-5-phenylimidazolidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060866
     RDKit          3D
Phenytoin dihydrodiol
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.3464   -2.0467    3.4366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006   -1.8490    2.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -2.7823    1.1324 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0159   -2.1177   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0849   -2.7046   -1.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7224   -0.6951    0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6699   -0.3319   -0.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628   -0.0002    0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8674    0.3807    0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6054   -0.5401    1.5855 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4213    0.3922   -0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9418    1.6880   -0.8098 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5009    0.0150   -1.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550   -0.3102   -1.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6947    0.2125   -0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2821    1.3482   -1.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146    2.1689   -1.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5489    1.8639   -1.7712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9520    0.7204   -1.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0254   -0.1052   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9720   -0.5922    1.6185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -3.8159    1.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0490   -0.0086    1.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728    1.3837    1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9966   -0.1185    2.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3439   -0.2668   -0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8682    1.7686   -0.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8816    0.0110   -2.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952   -0.5847   -2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2540    1.6243   -1.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9102    3.0696   -2.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3182    2.4547   -2.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9790    0.4255   -1.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3266   -1.0009    0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725    0.3433    2.1173 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  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21  2  1  0
 14  7  1  0
 20 15  1  0
  3 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  O   UNK     0      -1.912   2.604   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.881   1.460   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.625   1.780   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.656   0.636   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.180  -0.829   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.326  -1.149   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.357  -0.005   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.863  -0.325   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.210  -1.973   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.456  -2.879   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.980  -4.343   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.885  -5.589   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       1.440  -4.343   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       0.964  -2.879   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.500  -2.403   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.241  -0.829   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.765   0.636   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.795   1.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.302   1.460   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.778  -0.005   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.747  -1.149   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10   14   16                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16    9   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0060866
HETATM    1  O1  UNL     1      -1.346  -2.047   3.437  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.201  -1.849   2.201  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.226  -2.782   1.132  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.016  -2.118  -0.107  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.085  -2.705  -1.217  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.722  -0.695   0.199  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.670  -0.332  -0.070  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.463  -0.000   0.935  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.867   0.381   0.799  1.00  0.00           C  
HETATM   10  O3  UNL     1       3.605  -0.540   1.586  1.00  0.00           O  
HETATM   11  C7  UNL     1       3.421   0.392  -0.570  1.00  0.00           C  
HETATM   12  O4  UNL     1       3.942   1.688  -0.810  1.00  0.00           O  
HETATM   13  C8  UNL     1       2.501   0.015  -1.659  1.00  0.00           C  
HETATM   14  C9  UNL     1       1.255  -0.310  -1.409  1.00  0.00           C  
HETATM   15  C10 UNL     1      -1.695   0.212  -0.495  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.282   1.348  -1.157  1.00  0.00           C  
HETATM   17  C12 UNL     1      -2.215   2.169  -1.792  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.549   1.864  -1.771  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.952   0.720  -1.104  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.025  -0.105  -0.466  1.00  0.00           C  
HETATM   21  N2  UNL     1      -0.972  -0.592   1.618  1.00  0.00           N  
HETATM   22  H1  UNL     1      -1.385  -3.816   1.312  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.049  -0.009   1.938  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.973   1.384   1.320  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.997  -0.119   2.370  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.344  -0.267  -0.601  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.868   1.769  -0.507  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.882   0.011  -2.698  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.595  -0.585  -2.229  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.254   1.624  -1.198  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.910   3.070  -2.320  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.318   2.455  -2.241  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.979   0.425  -1.050  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.327  -1.001   0.059  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.972   0.343   2.117  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4   22
CONECT    4    5    5    6
CONECT    6    7   15   21
CONECT    7    8    8   14
CONECT    8    9   23
CONECT    9   10   11   24
CONECT   10   25
CONECT   11   12   13   26
CONECT   12   27
CONECT   13   14   14   28
CONECT   14   29
CONECT   15   16   16   20
CONECT   16   17   30
CONECT   17   18   18   31
CONECT   18   19   32
CONECT   19   20   20   33
CONECT   20   34
CONECT   21   35
END

HMDB0060866
     RDKit          3D
Phenytoin dihydrodiol
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.3464   -2.0467    3.4366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006   -1.8490    2.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -2.7823    1.1324 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0159   -2.1177   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0849   -2.7046   -1.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7224   -0.6951    0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6699   -0.3319   -0.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628   -0.0002    0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8674    0.3807    0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6054   -0.5401    1.5855 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4213    0.3922   -0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9418    1.6880   -0.8098 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5009    0.0150   -1.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550   -0.3102   -1.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6947    0.2125   -0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2821    1.3482   -1.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146    2.1689   -1.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5489    1.8639   -1.7712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9520    0.7204   -1.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0254   -0.1052   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9720   -0.5922    1.6185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -3.8159    1.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0490   -0.0086    1.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728    1.3837    1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9966   -0.1185    2.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3439   -0.2668   -0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8682    1.7686   -0.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8816    0.0110   -2.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952   -0.5847   -2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2540    1.6243   -1.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9102    3.0696   -2.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3182    2.4547   -2.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9790    0.4255   -1.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3266   -1.0009    0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725    0.3433    2.1173 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  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21  2  1  0
 14  7  1  0
 20 15  1  0
  3 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-(3,4-Dihydroxy-1,5-cyclohexadien-1-yl)-5-phenylhydantoin, (3R-(1(r*),3alpha,4beta))-isomer	HMDB
5-(3,4-Dihydroxy-1,5-cyclohexadien-1-yl)-5-phenylhydantoin, (3R-(1(s*),3alpha,4beta))-isomer	HMDB
5-DCYPH	HMDB
5-(3,4-Dihydroxy-1,5-cyclohexadien-1-yl)-5-phenylhydantoin	MeSH

Chemical Formula

C₁₅H₁₄N₂O₄

Average Molecular Weight

286.2827

Monoisotopic Molecular Weight

286.095356946

IUPAC Name

5-(3,4-dihydroxycyclohexa-1,5-dien-1-yl)-5-phenylimidazolidine-2,4-dione

Traditional Name

5-(3,4-dihydroxycyclohexa-1,5-dien-1-yl)-5-phenylimidazolidine-2,4-dione

CAS Registry Number

Not Available

SMILES

OC1C=CC(=CC1O)C1(NC(=O)NC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H14N2O4/c18-11-7-6-10(8-12(11)19)15(9-4-2-1-3-5-9)13(20)16-14(21)17-15/h1-8,11-12,18-19H,(H2,16,17,20,21)

InChI Key

FEEKFEKCXIDMIS-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
5-monosubstituted hydantoin
N-acyl urea
Ureide
Monocyclic benzene moiety
Benzenoid
Dicarboximide
Urea
Secondary alcohol
1,2-diol
Carbonic acid derivative
Azacycle
Carboxylic acid derivative
Alcohol
Organonitrogen compound
Organic oxygen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
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 (HMDB: HMDB0060866)

Organ

Kidney (HMDB: HMDB0060866)
Liver (HMDB: HMDB0060866)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060866)

Cellular substructure

Cytoplasm (HMDB: HMDB0060866)

Source

Endogenous

Endogenous (HMDB: HMDB0060866)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Phenytoin (Antiarrhythmic) Action Pathway (PathBank: SMP0000327)

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	1.71 g/L	ALOGPS
logP	0.02	ALOGPS
logP	-0.16	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	98.66 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.73 m³·mol⁻¹	ChemAxon
Polarizability	27.79 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]+	165.883	31661259
DarkChem	[M-H]-	160.779	31661259
DeepCCS	[M+H]+	171.617	30932474
DeepCCS	[M-H]-	169.259	30932474
DeepCCS	[M-2H]-	202.145	30932474
DeepCCS	[M+Na]+	177.71	30932474
AllCCS	[M+H]+	167.4	32859911
AllCCS	[M+H-H2O]+	163.7	32859911
AllCCS	[M+NH4]+	170.8	32859911
AllCCS	[M+Na]+	171.8	32859911
AllCCS	[M-H]-	167.1	32859911
AllCCS	[M+Na-2H]-	166.6	32859911
AllCCS	[M+HCOO]-	166.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenytoin dihydrodiol	OC1C=CC(=CC1O)C1(NC(=O)NC1=O)C1=CC=CC=C1	4014.6	Standard polar	33892256
Phenytoin dihydrodiol	OC1C=CC(=CC1O)C1(NC(=O)NC1=O)C1=CC=CC=C1	2812.9	Standard non polar	33892256
Phenytoin dihydrodiol	OC1C=CC(=CC1O)C1(NC(=O)NC1=O)C1=CC=CC=C1	2826.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenytoin dihydrodiol,1TMS,isomer #1	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)NC(=O)NC2=O)=CC1O	2845.0	Semi standard non polar	33892256
Phenytoin dihydrodiol,1TMS,isomer #2	C[Si](C)(C)OC1C=C(C2(C3=CC=CC=C3)NC(=O)NC2=O)C=CC1O	2848.4	Semi standard non polar	33892256
Phenytoin dihydrodiol,1TMS,isomer #3	C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC(O)C(O)C=C1)C1=CC=CC=C1	2739.3	Semi standard non polar	33892256
Phenytoin dihydrodiol,1TMS,isomer #4	C[Si](C)(C)N1C(=O)NC(C2=CC(O)C(O)C=C2)(C2=CC=CC=C2)C1=O	2761.2	Semi standard non polar	33892256
Phenytoin dihydrodiol,2TMS,isomer #1	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)NC(=O)NC2=O)=CC1O[Si](C)(C)C	2887.0	Semi standard non polar	33892256
Phenytoin dihydrodiol,2TMS,isomer #2	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)=CC1O	2722.5	Semi standard non polar	33892256
Phenytoin dihydrodiol,2TMS,isomer #3	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)=CC1O	2799.1	Semi standard non polar	33892256
Phenytoin dihydrodiol,2TMS,isomer #4	C[Si](C)(C)OC1C=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)C=CC1O	2702.1	Semi standard non polar	33892256
Phenytoin dihydrodiol,2TMS,isomer #5	C[Si](C)(C)OC1C=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)C=CC1O	2782.6	Semi standard non polar	33892256
Phenytoin dihydrodiol,2TMS,isomer #6	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC(O)C(O)C=C2)(C2=CC=CC=C2)C1=O	2531.0	Semi standard non polar	33892256
Phenytoin dihydrodiol,3TMS,isomer #1	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)=CC1O[Si](C)(C)C	2708.7	Semi standard non polar	33892256
Phenytoin dihydrodiol,3TMS,isomer #1	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)=CC1O[Si](C)(C)C	2634.7	Standard non polar	33892256
Phenytoin dihydrodiol,3TMS,isomer #1	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)=CC1O[Si](C)(C)C	3759.3	Standard polar	33892256
Phenytoin dihydrodiol,3TMS,isomer #2	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)=CC1O[Si](C)(C)C	2805.1	Semi standard non polar	33892256
Phenytoin dihydrodiol,3TMS,isomer #2	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)=CC1O[Si](C)(C)C	2600.2	Standard non polar	33892256
Phenytoin dihydrodiol,3TMS,isomer #2	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)=CC1O[Si](C)(C)C	3666.5	Standard polar	33892256
Phenytoin dihydrodiol,3TMS,isomer #3	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=CC1O	2525.5	Semi standard non polar	33892256
Phenytoin dihydrodiol,3TMS,isomer #3	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=CC1O	2582.6	Standard non polar	33892256
Phenytoin dihydrodiol,3TMS,isomer #3	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=CC1O	3431.6	Standard polar	33892256
Phenytoin dihydrodiol,3TMS,isomer #4	C[Si](C)(C)OC1C=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)C=CC1O	2503.5	Semi standard non polar	33892256
Phenytoin dihydrodiol,3TMS,isomer #4	C[Si](C)(C)OC1C=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)C=CC1O	2611.5	Standard non polar	33892256
Phenytoin dihydrodiol,3TMS,isomer #4	C[Si](C)(C)OC1C=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)C=CC1O	3442.7	Standard polar	33892256
Phenytoin dihydrodiol,4TMS,isomer #1	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=CC1O[Si](C)(C)C	2536.0	Semi standard non polar	33892256
Phenytoin dihydrodiol,4TMS,isomer #1	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=CC1O[Si](C)(C)C	2655.5	Standard non polar	33892256
Phenytoin dihydrodiol,4TMS,isomer #1	C[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=CC1O[Si](C)(C)C	3116.8	Standard polar	33892256
Phenytoin dihydrodiol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)NC(=O)NC2=O)=CC1O	3099.3	Semi standard non polar	33892256
Phenytoin dihydrodiol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C=C(C2(C3=CC=CC=C3)NC(=O)NC2=O)C=CC1O	3097.1	Semi standard non polar	33892256
Phenytoin dihydrodiol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC(O)C(O)C=C1)C1=CC=CC=C1	3013.0	Semi standard non polar	33892256
Phenytoin dihydrodiol,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC(O)C(O)C=C2)(C2=CC=CC=C2)C1=O	3067.1	Semi standard non polar	33892256
Phenytoin dihydrodiol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)NC(=O)NC2=O)=CC1O[Si](C)(C)C(C)(C)C	3353.9	Semi standard non polar	33892256
Phenytoin dihydrodiol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)=CC1O	3219.9	Semi standard non polar	33892256
Phenytoin dihydrodiol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)=CC1O	3318.2	Semi standard non polar	33892256
Phenytoin dihydrodiol,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1C=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)C=CC1O	3207.5	Semi standard non polar	33892256
Phenytoin dihydrodiol,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1C=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=CC1O	3311.0	Semi standard non polar	33892256
Phenytoin dihydrodiol,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC(O)C(O)C=C2)(C2=CC=CC=C2)C1=O	3073.8	Semi standard non polar	33892256
Phenytoin dihydrodiol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)=CC1O[Si](C)(C)C(C)(C)C	3357.3	Semi standard non polar	33892256
Phenytoin dihydrodiol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)=CC1O[Si](C)(C)C(C)(C)C	3188.7	Standard non polar	33892256
Phenytoin dihydrodiol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)=CC1O[Si](C)(C)C(C)(C)C	3826.7	Standard polar	33892256
Phenytoin dihydrodiol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)=CC1O[Si](C)(C)C(C)(C)C	3492.2	Semi standard non polar	33892256
Phenytoin dihydrodiol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)=CC1O[Si](C)(C)C(C)(C)C	3173.3	Standard non polar	33892256
Phenytoin dihydrodiol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)=CC1O[Si](C)(C)C(C)(C)C	3848.8	Standard polar	33892256
Phenytoin dihydrodiol,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=CC1O	3241.8	Semi standard non polar	33892256
Phenytoin dihydrodiol,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=CC1O	3181.0	Standard non polar	33892256
Phenytoin dihydrodiol,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=CC1O	3566.2	Standard polar	33892256
Phenytoin dihydrodiol,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1C=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)C=CC1O	3233.6	Semi standard non polar	33892256
Phenytoin dihydrodiol,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1C=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)C=CC1O	3233.2	Standard non polar	33892256
Phenytoin dihydrodiol,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1C=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)C=CC1O	3587.4	Standard polar	33892256
Phenytoin dihydrodiol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=CC1O[Si](C)(C)C(C)(C)C	3390.2	Semi standard non polar	33892256
Phenytoin dihydrodiol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=CC1O[Si](C)(C)C(C)(C)C	3410.4	Standard non polar	33892256
Phenytoin dihydrodiol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=CC1O[Si](C)(C)C(C)(C)C	3316.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin dihydrodiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0950000000-89919a7516318c7f348b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin dihydrodiol GC-MS (2 TMS) - 70eV, Positive	splash10-004i-4927100000-8e79695de718bd3f8643	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin dihydrodiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin dihydrodiol 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 - Phenytoin dihydrodiol 10V, Positive-QTOF	splash10-014r-0090000000-4fe822b10c51f1b29452	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin dihydrodiol 20V, Positive-QTOF	splash10-014i-0590000000-28a098e3f4129e41d069	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin dihydrodiol 40V, Positive-QTOF	splash10-0nmj-0900000000-3f7271c0a16558d84b68	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin dihydrodiol 10V, Negative-QTOF	splash10-000i-0090000000-88fa9b279c070097c973	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin dihydrodiol 20V, Negative-QTOF	splash10-000f-4190000000-b8afa3f05c7d6a331afd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin dihydrodiol 40V, Negative-QTOF	splash10-0udl-5910000000-eaa2ce2653655f9d2e22	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin dihydrodiol 10V, Positive-QTOF	splash10-000i-0090000000-020204f16876319b6c3f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin dihydrodiol 20V, Positive-QTOF	splash10-00ks-0490000000-5c06fe2f2ce9247ee955	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin dihydrodiol 40V, Positive-QTOF	splash10-0j7j-2950000000-7cca93c0e4555b0a4094	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin dihydrodiol 10V, Negative-QTOF	splash10-000i-0090000000-4a8080597a5d1f7abe98	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin dihydrodiol 20V, Negative-QTOF	splash10-002f-8690000000-7ec322a0350cf0a9fa9c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin dihydrodiol 40V, Negative-QTOF	splash10-0006-9500000000-16cc1d15c1c52bf202e0	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

152954

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Phenytoin dihydrodiol (HMDB0060866)

MOL for HMDB0060866 (Phenytoin dihydrodiol)

3D MOL for HMDB0060866 (Phenytoin dihydrodiol)

3D SDF for HMDB0060866 (Phenytoin dihydrodiol)

3D-SDF for HMDB0060866 (Phenytoin dihydrodiol)

PDB for HMDB0060866 (Phenytoin dihydrodiol)

3D PDB for HMDB0060866 (Phenytoin dihydrodiol)

SMILES for HMDB0060866 (Phenytoin dihydrodiol)

INCHI for HMDB0060866 (Phenytoin dihydrodiol)

Structure for HMDB0060866 (Phenytoin dihydrodiol)

3D Structure for HMDB0060866 (Phenytoin dihydrodiol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra