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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:04:18 UTC

Update Date

2021-09-14 15:46:40 UTC

HMDB ID

HMDB0060864

Secondary Accession Numbers

HMDB60864

Metabolite Identification

Common Name

Phenytoin arene-oxide

Description

Phenytoin arene-oxide 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 arene-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, phenytoin arene-oxide participates in a number of enzymatic reactions. In particular, phenytoin arene-oxide can be biosynthesized from phenytoin; which is catalyzed by the enzymes cytochrome P450 2C19 and cytochrome P450 2C9. In addition, phenytoin arene-oxide can be converted into phenytoin dihydrodiol; which is mediated by the enzymes cytochrome P450 1A2, cytochrome P450 2C19, cytochrome P450 2E1, and epoxide hydrolase 1. Phenytoin arene-oxide is a metabolite of phenytoin. In humans, phenytoin arene-oxide 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. Phenytoin sodium is a commonly used antiepileptic.

Structure

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

HMDB0060864
     RDKit          3D
Phenytoin arene-oxide
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.0008   -3.2556   -2.7251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1309   -2.6481   -1.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2401   -3.1085   -0.3477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1023   -2.0810    0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1682   -2.3086    1.7992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304   -0.8514   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9729   -0.1089   -0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0277    1.1517    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688    1.9609    0.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7974    2.2502   -1.2010 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4268    1.2727   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -0.1329   -0.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1649   -0.7601   -0.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3332    0.0418    0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2426    0.6480   -0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2345    1.4997    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3114    1.7443    1.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    1.1378    2.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4218    0.2996    1.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6953   -1.3434   -1.4992 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908   -4.0523   -0.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1181    1.6483    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485    2.7299    0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4288    1.5563    0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2119   -0.6502   -1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0899   -1.8071   -1.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795    0.5351   -1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9485    1.9715   -0.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881    2.4115    1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4418    1.3175    3.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7207   -0.1596    2.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2461   -0.9090   -2.2555 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
 10 11  1  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20  2  1  0
 13  7  1  0
 19 14  1  0
 11  9  1  0
  3 21  1  0
  8 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END


  Mrv0541 07041312042D          

 20 23  0  0  0  0            999 V2000
    2.8333   -1.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9109   -0.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6210   -0.4703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4411    0.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9866    0.9537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2921   -0.3446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8582    1.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2934    1.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5319    2.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3351    2.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998    2.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6614    1.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060864

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC2OC2C=C1

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

> <INCHI_KEY>
WBRFFCOFWKCXFD-UHFFFAOYSA-N

> <FORMULA>
C15H12N2O3

> <MOLECULAR_WEIGHT>
268.2674

> <EXACT_MASS>
268.08479226

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.137108865921125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-{7-oxabicyclo[4.1.0]hepta-2,4-dien-3-yl}-5-phenylimidazolidine-2,4-dione

> <ALOGPS_LOGP>
0.68

> <JCHEM_LOGP>
0.9987990873333332

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.18101415922207

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.45949831575009

> <JCHEM_PKA_STRONGEST_BASIC>
-4.262568254126492

> <JCHEM_POLAR_SURFACE_AREA>
70.73

> <JCHEM_REFRACTIVITY>
72.21620000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{7-oxabicyclo[4.1.0]hepta-2,4-dien-3-yl}-5-phenylimidazolidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060864
     RDKit          3D
Phenytoin arene-oxide
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.0008   -3.2556   -2.7251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1309   -2.6481   -1.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2401   -3.1085   -0.3477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1023   -2.0810    0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1682   -2.3086    1.7992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304   -0.8514   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9729   -0.1089   -0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0277    1.1517    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688    1.9609    0.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7974    2.2502   -1.2010 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4268    1.2727   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -0.1329   -0.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1649   -0.7601   -0.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3332    0.0418    0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2426    0.6480   -0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2345    1.4997    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3114    1.7443    1.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    1.1378    2.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4218    0.2996    1.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6953   -1.3434   -1.4992 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908   -4.0523   -0.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1181    1.6483    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485    2.7299    0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4288    1.5563    0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2119   -0.6502   -1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0899   -1.8071   -1.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795    0.5351   -1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9485    1.9715   -0.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881    2.4115    1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4418    1.3175    3.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7207   -0.1596    2.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2461   -0.9090   -2.2555 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
 10 11  1  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20  2  1  0
 13  7  1  0
 19 14  1  0
 11  9  1  0
  3 21  1  0
  8 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  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       5.289  -3.195   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.434  -1.662   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.759  -0.878   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.423   0.625   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.442   1.780   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.890   0.770   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.279  -0.643   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.335   2.244   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.281   3.367   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.726   4.841   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.226   5.193   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.280   4.070   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.835   2.596   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.557   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.223   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.889   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.445   2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.889   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.223   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.557   3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8   14                                             
CONECT    7    6    2                                                       
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    6   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   18                                                       
CONECT   18   17   16   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0060864
HETATM    1  O1  UNL     1       0.001  -3.256  -2.725  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.131  -2.648  -1.638  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.240  -3.109  -0.348  1.00  0.00           N  
HETATM    4  C2  UNL     1      -0.102  -2.081   0.564  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.168  -2.309   1.799  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.330  -0.851  -0.188  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.973  -0.109  -0.271  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.028   1.152   0.106  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.269   1.961   0.057  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.797   2.250  -1.201  1.00  0.00           O  
HETATM   11  C7  UNL     1       3.427   1.273  -0.427  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.308  -0.133  -0.839  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.165  -0.760  -0.760  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.333   0.042   0.390  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.243   0.648  -0.435  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.234   1.500   0.051  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.311   1.744   1.385  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.400   1.138   2.219  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.422   0.300   1.751  1.00  0.00           C  
HETATM   20  N2  UNL     1      -0.695  -1.343  -1.499  1.00  0.00           N  
HETATM   21  H1  UNL     1       0.691  -4.052  -0.121  1.00  0.00           H  
HETATM   22  H2  UNL     1       0.118   1.648   0.473  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.349   2.730   0.862  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.429   1.556   0.024  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.212  -0.650  -1.219  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.090  -1.807  -1.068  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.279   0.535  -1.516  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.949   1.971  -0.626  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.088   2.411   1.769  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.442   1.317   3.281  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.721  -0.160   2.406  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.246  -0.909  -2.256  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4   21
CONECT    4    5    5    6
CONECT    6    7   14   20
CONECT    7    8    8   13
CONECT    8    9   22
CONECT    9   10   11   23
CONECT   10   11
CONECT   11   12   24
CONECT   12   13   13   25
CONECT   13   26
CONECT   14   15   15   19
CONECT   15   16   27
CONECT   16   17   17   28
CONECT   17   18   29
CONECT   18   19   19   30
CONECT   19   31
CONECT   20   32
END

HMDB0060864
     RDKit          3D
Phenytoin arene-oxide
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.0008   -3.2556   -2.7251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1309   -2.6481   -1.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2401   -3.1085   -0.3477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1023   -2.0810    0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1682   -2.3086    1.7992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304   -0.8514   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9729   -0.1089   -0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0277    1.1517    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688    1.9609    0.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7974    2.2502   -1.2010 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4268    1.2727   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -0.1329   -0.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1649   -0.7601   -0.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3332    0.0418    0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2426    0.6480   -0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2345    1.4997    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3114    1.7443    1.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    1.1378    2.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4218    0.2996    1.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6953   -1.3434   -1.4992 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908   -4.0523   -0.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1181    1.6483    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485    2.7299    0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4288    1.5563    0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2119   -0.6502   -1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0899   -1.8071   -1.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795    0.5351   -1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9485    1.9715   -0.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881    2.4115    1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4418    1.3175    3.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7207   -0.1596    2.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2461   -0.9090   -2.2555 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
 10 11  1  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20  2  1  0
 13  7  1  0
 19 14  1  0
 11  9  1  0
  3 21  1  0
  8 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂N₂O₃

Average Molecular Weight

268.2674

Monoisotopic Molecular Weight

268.08479226

IUPAC Name

5-{7-oxabicyclo[4.1.0]hepta-2,4-dien-3-yl}-5-phenylimidazolidine-2,4-dione

Traditional Name

5-{7-oxabicyclo[4.1.0]hepta-2,4-dien-3-yl}-5-phenylimidazolidine-2,4-dione

CAS Registry Number

Not Available

SMILES

O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC2OC2C=C1

InChI Identifier

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

InChI Key

WBRFFCOFWKCXFD-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
Carbonic acid derivative
Urea
Azacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	0.68	ALOGPS
logP	1	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.73 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72.22 m³·mol⁻¹	ChemAxon
Polarizability	26.14 Å³	ChemAxon
Number of Rings	4	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]+	164.077	31661259
DarkChem	[M-H]-	156.229	31661259
DeepCCS	[M+H]+	158.109	30932474
DeepCCS	[M-H]-	155.751	30932474
DeepCCS	[M-2H]-	188.641	30932474
DeepCCS	[M+Na]+	164.202	30932474
AllCCS	[M+H]+	162.4	32859911
AllCCS	[M+H-H2O]+	158.6	32859911
AllCCS	[M+NH4]+	166.0	32859911
AllCCS	[M+Na]+	167.0	32859911
AllCCS	[M-H]-	164.8	32859911
AllCCS	[M+Na-2H]-	164.1	32859911
AllCCS	[M+HCOO]-	163.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.49 minutes	32390414
Predicted by Siyang on May 30, 2022	12.121 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.58 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2055.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	317.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	136.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	195.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	100.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	371.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	471.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1069.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	404.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1326.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	310.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	316.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	442.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	173.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	34.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenytoin arene-oxide	O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC2OC2C=C1	3887.8	Standard polar	33892256
Phenytoin arene-oxide	O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC2OC2C=C1	2399.2	Standard non polar	33892256
Phenytoin arene-oxide	O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC2OC2C=C1	2487.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenytoin arene-oxide,1TMS,isomer #1	C[Si](C)(C)N1C(=O)NC(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O	2649.8	Semi standard non polar	33892256
Phenytoin arene-oxide,1TMS,isomer #1	C[Si](C)(C)N1C(=O)NC(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O	2331.5	Standard non polar	33892256
Phenytoin arene-oxide,1TMS,isomer #1	C[Si](C)(C)N1C(=O)NC(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O	3665.8	Standard polar	33892256
Phenytoin arene-oxide,1TMS,isomer #2	C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC2OC2C=C1)C1=CC=CC=C1	2636.1	Semi standard non polar	33892256
Phenytoin arene-oxide,1TMS,isomer #2	C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC2OC2C=C1)C1=CC=CC=C1	2347.1	Standard non polar	33892256
Phenytoin arene-oxide,1TMS,isomer #2	C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC2OC2C=C1)C1=CC=CC=C1	3795.7	Standard polar	33892256
Phenytoin arene-oxide,2TMS,isomer #1	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O	2417.7	Semi standard non polar	33892256
Phenytoin arene-oxide,2TMS,isomer #1	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O	2408.9	Standard non polar	33892256
Phenytoin arene-oxide,2TMS,isomer #1	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O	3299.8	Standard polar	33892256
Phenytoin arene-oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O	2934.1	Semi standard non polar	33892256
Phenytoin arene-oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O	2544.6	Standard non polar	33892256
Phenytoin arene-oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O	3737.3	Standard polar	33892256
Phenytoin arene-oxide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC2OC2C=C1)C1=CC=CC=C1	2882.1	Semi standard non polar	33892256
Phenytoin arene-oxide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC2OC2C=C1)C1=CC=CC=C1	2554.2	Standard non polar	33892256
Phenytoin arene-oxide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC2OC2C=C1)C1=CC=CC=C1	3798.9	Standard polar	33892256
Phenytoin arene-oxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O	2927.8	Semi standard non polar	33892256
Phenytoin arene-oxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O	2844.6	Standard non polar	33892256
Phenytoin arene-oxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O	3353.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin arene-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-3900000000-9efa4bfdf4f72f2f2514	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin arene-oxide 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 arene-oxide 10V, Positive-QTOF	splash10-014j-0890000000-b1ac67ebfe6d31156307	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin arene-oxide 20V, Positive-QTOF	splash10-0002-0900000000-798f9ccb530dd8c07282	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin arene-oxide 40V, Positive-QTOF	splash10-0fu6-3900000000-3c0913b08bb8cc2b3943	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin arene-oxide 10V, Negative-QTOF	splash10-014i-0090000000-2fd54e3b6725c2e1b6cb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin arene-oxide 20V, Negative-QTOF	splash10-014i-3390000000-68e5a4d4466d694c4875	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin arene-oxide 40V, Negative-QTOF	splash10-0f6x-4900000000-56adc3c0900052f75a89	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin arene-oxide 10V, Negative-QTOF	splash10-014i-0090000000-bd7cd943428e7be367e7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin arene-oxide 20V, Negative-QTOF	splash10-0006-9540000000-7cb9b44ddb94c5029581	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin arene-oxide 40V, Negative-QTOF	splash10-0006-9500000000-052a6f128f9a89805f40	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin arene-oxide 10V, Positive-QTOF	splash10-014i-0090000000-bab633482800eb8f5ea1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin arene-oxide 20V, Positive-QTOF	splash10-00ls-0950000000-76342d8c21289fc13d3e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin arene-oxide 40V, Positive-QTOF	splash10-0f8a-2910000000-c5d591694a524a054407	2021-10-12	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

101592230

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 arene-oxide (HMDB0060864)

MOL for HMDB0060864 (Phenytoin arene-oxide)

3D MOL for HMDB0060864 (Phenytoin arene-oxide)

3D SDF for HMDB0060864 (Phenytoin arene-oxide)

3D-SDF for HMDB0060864 (Phenytoin arene-oxide)

PDB for HMDB0060864 (Phenytoin arene-oxide)

3D PDB for HMDB0060864 (Phenytoin arene-oxide)

SMILES for HMDB0060864 (Phenytoin arene-oxide)

INCHI for HMDB0060864 (Phenytoin arene-oxide)

Structure for HMDB0060864 (Phenytoin arene-oxide)

3D Structure for HMDB0060864 (Phenytoin arene-oxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra