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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:04:30 UTC

Update Date

2021-09-14 15:46:31 UTC

HMDB ID

HMDB0060868

Secondary Accession Numbers

HMDB60868

Metabolite Identification

Common Name

Phenytoin quinone

Description

Phenytoin quinone 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 quinone is an extremely weak basic (essentially neutral) compound (based on its pKa). phenytoin quinone can be biosynthesized from phenytoin catechol; which is mediated by the enzyme nad(p)H dehydrogenase [quinone] 1. In humans, phenytoin quinone is involved in the metabolic disorder called the phenytoin (antiarrhythmic) action pathway. It is sometimes considered a class 1b antiarrhythmic. Phenytoin quinone is a metabolite of phenytoin. Phenytoin sodium is a commonly used antiepileptic. 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

HMDB0060868
     RDKit          3D
Phenytoin quinone
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.1932    4.3318    0.2503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640    3.1283   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474    2.7772   -1.5325 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1114    1.3691   -1.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2756    0.7275   -2.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0601    0.7804   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319   -0.0945    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1096    0.2333    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2699   -0.5810    1.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0831   -0.2357    2.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890   -1.8120    0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4786   -2.5600    0.8001 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -2.1343   -0.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4754   -1.3171   -0.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1973    0.0251   -0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8369    0.1254    1.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0128   -0.5479    1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725   -1.3303    0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8991   -1.3897   -0.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7093   -0.7274   -1.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814    1.9581    0.6134 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326    3.3999   -2.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9793    1.1343    1.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6215   -3.0433   -1.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092   -1.6541   -1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4346    0.7194    2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5721   -0.5255    2.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4994   -1.8693    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3098   -1.9907   -1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2852   -0.8460   -2.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.9491    1.6468 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
  9 11  1  0
 11 12  2  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
 13 24  1  0
 14 25  1  0
 16 26  1  0
 17 27  1  0
 18 28  1  0
 19 29  1  0
 20 30  1  0
 21 31  1  0
M  END


  Mrv0541 07041312042D          

 21 23  0  0  0  0            999 V2000
   -0.5275   -3.0841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0425   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7825   -2.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0374   -1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220   -1.3771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3700   -1.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -1.6320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9772   -0.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7973    0.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4046    0.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918    0.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3718   -0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7645   -0.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0350   -0.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8600   -0.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2650    0.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0899    0.3077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8450    1.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500    1.7279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0201    1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3849    0.2817    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  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 14 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060868

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H10N2O4/c18-11-7-6-10(8-12(11)19)15(9-4-2-1-3-5-9)13(20)16-14(21)17-15/h1-8H,(H2,16,17,20,21)

> <INCHI_KEY>
AWCFFJFKIPSEFH-UHFFFAOYSA-N

> <FORMULA>
C15H10N2O4

> <MOLECULAR_WEIGHT>
282.2509

> <EXACT_MASS>
282.064056818

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.43641629114896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
1.3718262989999996

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.019985833787594

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.444489596789872

> <JCHEM_PKA_STRONGEST_BASIC>
-8.31334338790228

> <JCHEM_POLAR_SURFACE_AREA>
92.34

> <JCHEM_REFRACTIVITY>
74.3431

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.04e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060868
     RDKit          3D
Phenytoin quinone
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.1932    4.3318    0.2503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640    3.1283   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474    2.7772   -1.5325 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1114    1.3691   -1.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2756    0.7275   -2.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0601    0.7804   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319   -0.0945    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1096    0.2333    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2699   -0.5810    1.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0831   -0.2357    2.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890   -1.8120    0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4786   -2.5600    0.8001 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -2.1343   -0.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4754   -1.3171   -0.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1973    0.0251   -0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8369    0.1254    1.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0128   -0.5479    1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725   -1.3303    0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8991   -1.3897   -0.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7093   -0.7274   -1.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814    1.9581    0.6134 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326    3.3999   -2.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9793    1.1343    1.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6215   -3.0433   -1.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092   -1.6541   -1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4346    0.7194    2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5721   -0.5255    2.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4994   -1.8693    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3098   -1.9907   -1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2852   -0.8460   -2.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.9491    1.6468 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
  9 11  1  0
 11 12  2  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
 13 24  1  0
 14 25  1  0
 16 26  1  0
 17 27  1  0
 18 28  1  0
 19 29  1  0
 20 30  1  0
 21 31  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      -0.985  -5.757   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.079  -4.511   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.461  -4.511   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.936  -3.046   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.401  -2.571   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.691  -2.141   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.555  -3.046   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.824  -1.099   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.488   0.404   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.622   1.446   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.091   0.986   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.427  -0.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.294  -1.559   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.065  -0.800   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.605  -0.783   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.361   0.558   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.901   0.574   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.577   1.884   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.333   3.225   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.038   1.868   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.718   0.526   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   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0060868
HETATM    1  O1  UNL     1      -0.193   4.332   0.250  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.064   3.128  -0.161  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.047   2.777  -1.533  1.00  0.00           N  
HETATM    4  C2  UNL     1       0.111   1.369  -1.598  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.276   0.727  -2.696  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.060   0.780  -0.246  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.232  -0.095   0.040  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.110   0.233   0.992  1.00  0.00           C  
HETATM    9  C6  UNL     1       3.270  -0.581   1.314  1.00  0.00           C  
HETATM   10  O3  UNL     1       4.083  -0.236   2.229  1.00  0.00           O  
HETATM   11  C7  UNL     1       3.489  -1.812   0.565  1.00  0.00           C  
HETATM   12  O4  UNL     1       4.479  -2.560   0.800  1.00  0.00           O  
HETATM   13  C8  UNL     1       2.511  -2.134  -0.465  1.00  0.00           C  
HETATM   14  C9  UNL     1       1.475  -1.317  -0.684  1.00  0.00           C  
HETATM   15  C10 UNL     1      -1.197   0.025  -0.042  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.837   0.125   1.198  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.013  -0.548   1.406  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.572  -1.330   0.390  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.899  -1.390  -0.805  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.709  -0.727  -1.062  1.00  0.00           C  
HETATM   21  N2  UNL     1       0.081   1.958   0.613  1.00  0.00           N  
HETATM   22  H1  UNL     1      -0.133   3.400  -2.385  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.979   1.134   1.558  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.621  -3.043  -1.059  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.809  -1.654  -1.478  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.435   0.719   2.005  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.572  -0.525   2.333  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.499  -1.869   0.535  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.310  -1.991  -1.615  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.285  -0.846  -2.046  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.179   1.949   1.647  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   10   11
CONECT   11   12   12   13
CONECT   13   14   14   24
CONECT   14   25
CONECT   15   16   16   20
CONECT   16   17   26
CONECT   17   18   18   27
CONECT   18   19   28
CONECT   19   20   20   29
CONECT   20   30
CONECT   21   31
END

HMDB0060868
     RDKit          3D
Phenytoin quinone
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.1932    4.3318    0.2503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640    3.1283   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474    2.7772   -1.5325 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1114    1.3691   -1.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2756    0.7275   -2.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0601    0.7804   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319   -0.0945    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1096    0.2333    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2699   -0.5810    1.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0831   -0.2357    2.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890   -1.8120    0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4786   -2.5600    0.8001 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -2.1343   -0.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4754   -1.3171   -0.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1973    0.0251   -0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8369    0.1254    1.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0128   -0.5479    1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725   -1.3303    0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8991   -1.3897   -0.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7093   -0.7274   -1.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814    1.9581    0.6134 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326    3.3999   -2.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9793    1.1343    1.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6215   -3.0433   -1.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092   -1.6541   -1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4346    0.7194    2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5721   -0.5255    2.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4994   -1.8693    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3098   -1.9907   -1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2852   -0.8460   -2.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.9491    1.6468 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
  9 11  1  0
 11 12  2  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
 13 24  1  0
 14 25  1  0
 16 26  1  0
 17 27  1  0
 18 28  1  0
 19 29  1  0
 20 30  1  0
 21 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₀N₂O₄

Average Molecular Weight

282.2509

Monoisotopic Molecular Weight

282.064056818

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H10N2O4/c18-11-7-6-10(8-12(11)19)15(9-4-2-1-3-5-9)13(20)16-14(21)17-15/h1-8H,(H2,16,17,20,21)

InChI Key

AWCFFJFKIPSEFH-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
O-benzoquinone
Quinone
5-monosubstituted hydantoin
N-acyl urea
Ureide
Monocyclic benzene moiety
Benzenoid
Dicarboximide
Urea
Carbonic acid derivative
Ketone
Cyclic ketone
Azacycle
Carboxylic acid derivative
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

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060868)
Liver (HMDB: HMDB0060868)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060868)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060868)

Cellular substructure

Cytoplasm (HMDB: HMDB0060868)

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	0.05 g/L	ALOGPS
logP	1.22	ALOGPS
logP	1.37	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.44	ChemAxon
pKa (Strongest Basic)	-8.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.34 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.34 m³·mol⁻¹	ChemAxon
Polarizability	26.44 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]+	167.836	31661259
DarkChem	[M-H]-	160.866	31661259
DeepCCS	[M+H]+	167.065	30932474
DeepCCS	[M-H]-	164.707	30932474
DeepCCS	[M-2H]-	198.38	30932474
DeepCCS	[M+Na]+	173.607	30932474
AllCCS	[M+H]+	163.9	32859911
AllCCS	[M+H-H2O]+	160.2	32859911
AllCCS	[M+NH4]+	167.4	32859911
AllCCS	[M+Na]+	168.4	32859911
AllCCS	[M-H]-	164.9	32859911
AllCCS	[M+Na-2H]-	164.3	32859911
AllCCS	[M+HCOO]-	163.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenytoin quinone	O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC(=O)C(=O)C=C1	4078.5	Standard polar	33892256
Phenytoin quinone	O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC(=O)C(=O)C=C1	2637.3	Standard non polar	33892256
Phenytoin quinone	O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC(=O)C(=O)C=C1	2822.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenytoin quinone,1TMS,isomer #1	C[Si](C)(C)N1C(=O)NC(C2=CC(=O)C(=O)C=C2)(C2=CC=CC=C2)C1=O	2876.7	Semi standard non polar	33892256
Phenytoin quinone,1TMS,isomer #1	C[Si](C)(C)N1C(=O)NC(C2=CC(=O)C(=O)C=C2)(C2=CC=CC=C2)C1=O	2530.4	Standard non polar	33892256
Phenytoin quinone,1TMS,isomer #1	C[Si](C)(C)N1C(=O)NC(C2=CC(=O)C(=O)C=C2)(C2=CC=CC=C2)C1=O	4117.2	Standard polar	33892256
Phenytoin quinone,1TMS,isomer #2	C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC(=O)C(=O)C=C1)C1=CC=CC=C1	2824.5	Semi standard non polar	33892256
Phenytoin quinone,1TMS,isomer #2	C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC(=O)C(=O)C=C1)C1=CC=CC=C1	2505.2	Standard non polar	33892256
Phenytoin quinone,1TMS,isomer #2	C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC(=O)C(=O)C=C1)C1=CC=CC=C1	4207.8	Standard polar	33892256
Phenytoin quinone,2TMS,isomer #1	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	2624.6	Semi standard non polar	33892256
Phenytoin quinone,2TMS,isomer #1	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	2577.6	Standard non polar	33892256
Phenytoin quinone,2TMS,isomer #1	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	3783.0	Standard polar	33892256
Phenytoin quinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC(=O)C(=O)C=C2)(C2=CC=CC=C2)C1=O	3173.0	Semi standard non polar	33892256
Phenytoin quinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC(=O)C(=O)C=C2)(C2=CC=CC=C2)C1=O	2735.1	Standard non polar	33892256
Phenytoin quinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC(=O)C(=O)C=C2)(C2=CC=CC=C2)C1=O	4198.7	Standard polar	33892256
Phenytoin quinone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC(=O)C(=O)C=C1)C1=CC=CC=C1	3093.6	Semi standard non polar	33892256
Phenytoin quinone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC(=O)C(=O)C=C1)C1=CC=CC=C1	2710.2	Standard non polar	33892256
Phenytoin quinone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC(=O)C(=O)C=C1)C1=CC=CC=C1	4243.4	Standard polar	33892256
Phenytoin quinone,2TBDMS,isomer #1	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	3180.6	Semi standard non polar	33892256
Phenytoin quinone,2TBDMS,isomer #1	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	2992.9	Standard non polar	33892256
Phenytoin quinone,2TBDMS,isomer #1	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	3856.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin quinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gvk-1970000000-bcec85a1fc21800a28c9	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin quinone 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 quinone 10V, Positive-QTOF	splash10-01q9-0090000000-59f0c54e3a594c163ea5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin quinone 20V, Positive-QTOF	splash10-03di-0290000000-5de8e8c2554a742e8126	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin quinone 40V, Positive-QTOF	splash10-0pe9-1900000000-58d1e6fb63fb29b5b15c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin quinone 10V, Negative-QTOF	splash10-001i-0090000000-4c571b69f8a9f4703615	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin quinone 20V, Negative-QTOF	splash10-001i-3090000000-c26dcfdd90082c34ab89	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin quinone 40V, Negative-QTOF	splash10-0006-9740000000-c38c1abdf1e6dd18237f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin quinone 10V, Positive-QTOF	splash10-001i-0090000000-3150e6cfd6c25b7f7c89	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin quinone 20V, Positive-QTOF	splash10-03di-0390000000-8ef9d58a07f422af3875	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin quinone 40V, Positive-QTOF	splash10-0gx0-1930000000-7e95f739021e036da0e7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin quinone 10V, Negative-QTOF	splash10-001i-0090000000-474ffadd74c35f44454a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin quinone 20V, Negative-QTOF	splash10-01ox-6290000000-8ff792d77c663cffdf37	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin quinone 40V, Negative-QTOF	splash10-0006-9510000000-2dbcbbd5985ee2d625fd	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

131769980

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 quinone (HMDB0060868)

MOL for HMDB0060868 (Phenytoin quinone)

3D MOL for HMDB0060868 (Phenytoin quinone)

3D SDF for HMDB0060868 (Phenytoin quinone)

3D-SDF for HMDB0060868 (Phenytoin quinone)

PDB for HMDB0060868 (Phenytoin quinone)

3D PDB for HMDB0060868 (Phenytoin quinone)

SMILES for HMDB0060868 (Phenytoin quinone)

INCHI for HMDB0060868 (Phenytoin quinone)

Structure for HMDB0060868 (Phenytoin quinone)

3D Structure for HMDB0060868 (Phenytoin quinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra