Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:04:27 UTC

Update Date

2021-09-14 14:57:12 UTC

HMDB ID

HMDB0060867

Secondary Accession Numbers

HMDB60867

Metabolite Identification

Common Name

Phenytoin methylcatechol

Description

Phenytoin methylcatechol 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 methylcatechol is an extremely weak basic (essentially neutral) compound (based on its pKa). phenytoin methylcatechol and S-adenosylhomocysteine can be biosynthesized from phenytoin catechol and S-adenosylmethionine; which is mediated by the enzyme catechol O-methyltransferase. In humans, phenytoin methylcatechol 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. Phenytoin methylcatechol is a metabolite of phenytoin.

Structure

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

HMDB0060867
     RDKit          3D
Phenytoin methylcatechol
 34 36  0  0  0  0  0  0  0  0999 V2000
    4.4454    1.6469   -1.1900 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4295    0.4953   -0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2083   -0.0692   -0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    0.6604   -0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537    0.1161    0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4244    0.8405    0.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5673   -0.0260   -0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6032   -0.5254   -1.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6629   -1.3411   -1.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6798   -1.6485   -0.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6445   -1.1482    0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -0.3453    0.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    1.4061    1.6373 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4591    2.6110    1.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1395    3.2618    2.3131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923    2.9928    0.0930 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4651    2.0084   -0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0735    2.1864   -1.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873   -1.1610    0.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472   -1.9147    0.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1911   -1.3424    0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3780   -2.0661    0.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3343   -0.0781   -0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313    1.6618   -0.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8254   -0.3043   -2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622   -1.7192   -2.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4928   -2.2792   -1.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4362   -1.3775    1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5268    0.0716    1.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4998    1.0200    2.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6961    3.8495   -0.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0087   -1.5789    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -2.9132    1.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469   -2.9903    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 17  6  1  0
 12  7  1  0
  2 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
 22 34  1  0
M  END

  Mrv0541 07041312042D          

 22 24  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
    0.5899    1.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3968    1.9097    0.0000 O   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
    1.1841   -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  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060867

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(C=O)C=C(C=C1)C1(NC(=O)NC1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12N2O4/c19-9-10-8-12(6-7-13(10)20)16(11-4-2-1-3-5-11)14(21)17-15(22)18-16/h1-9,20H,(H2,17,18,21,22)

> <INCHI_KEY>
IVKHYRHKQDQYFC-UHFFFAOYSA-N

> <FORMULA>
C16H12N2O4

> <MOLECULAR_WEIGHT>
296.2775

> <EXACT_MASS>
296.079706882

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.63052613609162

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(2,5-dioxo-4-phenylimidazolidin-4-yl)-2-hydroxybenzaldehyde

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
2.206857403666666

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.48441480224923

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.302991849745576

> <JCHEM_PKA_STRONGEST_BASIC>
-5.988558854156129

> <JCHEM_POLAR_SURFACE_AREA>
95.5

> <JCHEM_REFRACTIVITY>
78.74720000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(2,5-dioxo-4-phenylimidazolidin-4-yl)-2-hydroxybenzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060867
     RDKit          3D
Phenytoin methylcatechol
 34 36  0  0  0  0  0  0  0  0999 V2000
    4.4454    1.6469   -1.1900 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4295    0.4953   -0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2083   -0.0692   -0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    0.6604   -0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537    0.1161    0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4244    0.8405    0.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5673   -0.0260   -0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6032   -0.5254   -1.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6629   -1.3411   -1.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6798   -1.6485   -0.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6445   -1.1482    0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -0.3453    0.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    1.4061    1.6373 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4591    2.6110    1.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1395    3.2618    2.3131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923    2.9928    0.0930 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4651    2.0084   -0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0735    2.1864   -1.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873   -1.1610    0.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472   -1.9147    0.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1911   -1.3424    0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3780   -2.0661    0.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3343   -0.0781   -0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313    1.6618   -0.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8254   -0.3043   -2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622   -1.7192   -2.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4928   -2.2792   -1.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4362   -1.3775    1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5268    0.0716    1.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4998    1.0200    2.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6961    3.8495   -0.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0087   -1.5789    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -2.9132    1.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469   -2.9903    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 17  6  1  0
 12  7  1  0
  2 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
 22 34  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       1.101   3.245   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.607   3.565   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.656   0.636   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.180  -0.829   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.326  -1.149   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.357  -0.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.210  -1.973   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       3.456  -2.879   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.980  -4.343   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.885  -5.589   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       1.440  -4.343   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       0.964  -2.879   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.500  -2.403   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.241  -0.829   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.765   0.636   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.795   1.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.302   1.460   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.778  -0.005   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.747  -1.149   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    2                                                       
CONECT   10    7   11   15   17                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
CONECT   17   10   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0060867
HETATM    1  O1  UNL     1       4.445   1.647  -1.190  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.430   0.495  -0.709  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.208  -0.069  -0.170  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.009   0.660  -0.170  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.854   0.116   0.345  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.424   0.840   0.362  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.567  -0.026  -0.040  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.603  -0.525  -1.318  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.663  -1.341  -1.729  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.680  -1.649  -0.850  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.645  -1.148   0.431  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.592  -0.345   0.818  1.00  0.00           C  
HETATM   13  N1  UNL     1      -0.742   1.406   1.637  1.00  0.00           N  
HETATM   14  C12 UNL     1      -1.459   2.611   1.450  1.00  0.00           C  
HETATM   15  O2  UNL     1      -2.139   3.262   2.313  1.00  0.00           O  
HETATM   16  N2  UNL     1      -1.292   2.993   0.093  1.00  0.00           N  
HETATM   17  C13 UNL     1      -0.465   2.008  -0.552  1.00  0.00           C  
HETATM   18  O3  UNL     1       0.073   2.186  -1.666  1.00  0.00           O  
HETATM   19  C14 UNL     1       0.887  -1.161   0.864  1.00  0.00           C  
HETATM   20  C15 UNL     1       2.047  -1.915   0.885  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.191  -1.342   0.361  1.00  0.00           C  
HETATM   22  O4  UNL     1       4.378  -2.066   0.362  1.00  0.00           O  
HETATM   23  H1  UNL     1       5.334  -0.078  -0.698  1.00  0.00           H  
HETATM   24  H2  UNL     1       2.031   1.662  -0.584  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.825  -0.304  -2.028  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.662  -1.719  -2.745  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.493  -2.279  -1.178  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.436  -1.378   1.144  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.527   0.072   1.822  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.500   1.020   2.576  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.696   3.850  -0.383  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.009  -1.579   1.262  1.00  0.00           H  
HETATM   33  H11 UNL     1       2.084  -2.913   1.289  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.447  -2.990   0.726  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   23
CONECT    3    4    4   21
CONECT    4    5   24
CONECT    5    6   19   19
CONECT    6    7   13   17
CONECT    7    8    8   12
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   11   27
CONECT   11   12   12   28
CONECT   12   29
CONECT   13   14   30
CONECT   14   15   15   16
CONECT   16   17   31
CONECT   17   18   18
CONECT   19   20   32
CONECT   20   21   21   33
CONECT   21   22
CONECT   22   34
END

HMDB0060867
     RDKit          3D
Phenytoin methylcatechol
 34 36  0  0  0  0  0  0  0  0999 V2000
    4.4454    1.6469   -1.1900 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4295    0.4953   -0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2083   -0.0692   -0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    0.6604   -0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537    0.1161    0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4244    0.8405    0.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5673   -0.0260   -0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6032   -0.5254   -1.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6629   -1.3411   -1.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6798   -1.6485   -0.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6445   -1.1482    0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -0.3453    0.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    1.4061    1.6373 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4591    2.6110    1.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1395    3.2618    2.3131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923    2.9928    0.0930 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4651    2.0084   -0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0735    2.1864   -1.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873   -1.1610    0.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472   -1.9147    0.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1911   -1.3424    0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3780   -2.0661    0.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3343   -0.0781   -0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313    1.6618   -0.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8254   -0.3043   -2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6622   -1.7192   -2.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4928   -2.2792   -1.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4362   -1.3775    1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5268    0.0716    1.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4998    1.0200    2.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6961    3.8495   -0.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0087   -1.5789    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -2.9132    1.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469   -2.9903    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 17  6  1  0
 12  7  1  0
  2 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂N₂O₄

Average Molecular Weight

296.2775

Monoisotopic Molecular Weight

296.079706882

IUPAC Name

5-(2,5-dioxo-4-phenylimidazolidin-4-yl)-2-hydroxybenzaldehyde

Traditional Name

5-(2,5-dioxo-4-phenylimidazolidin-4-yl)-2-hydroxybenzaldehyde

CAS Registry Number

Not Available

SMILES

OC1=C(C=O)C=C(C=C1)C1(NC(=O)NC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H12N2O4/c19-9-10-8-12(6-7-13(10)20)16(11-4-2-1-3-5-11)14(21)17-15(22)18-16/h1-9,20H,(H2,17,18,21,22)

InChI Key

IVKHYRHKQDQYFC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Phenylhydantoins

Alternative Parents

Substituents

Diphenylmethane
5-phenylhydantoin
Phenylimidazolidine
Alpha-amino acid or derivatives
Hydroxybenzaldehyde
Benzaldehyde
Benzoyl
5-monosubstituted hydantoin
1-hydroxy-2-unsubstituted benzenoid
N-acyl urea
Phenol
Aryl-aldehyde
Ureide
Monocyclic benzene moiety
Benzenoid
Dicarboximide
Vinylogous acid
Carbonic acid derivative
Urea
Azacycle
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Aldehyde
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060867)

Organ

Kidney (HMDB: HMDB0060867)
Liver (HMDB: HMDB0060867)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060867)

Cellular substructure

Cytoplasm (HMDB: HMDB0060867)
Membrane (HMDB: HMDB0060867)

Source

Endogenous

Endogenous (HMDB: HMDB0060867)

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	0.067 g/L	ALOGPS
logP	1.75	ALOGPS
logP	2.21	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.3	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.5 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.75 m³·mol⁻¹	ChemAxon
Polarizability	28.63 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]+	166.585	31661259
DarkChem	[M-H]-	164.344	31661259
DeepCCS	[M+H]+	174.062	30932474
DeepCCS	[M-H]-	171.704	30932474
DeepCCS	[M-2H]-	205.577	30932474
DeepCCS	[M+Na]+	180.804	30932474
AllCCS	[M+H]+	167.6	32859911
AllCCS	[M+H-H2O]+	164.0	32859911
AllCCS	[M+NH4]+	171.0	32859911
AllCCS	[M+Na]+	172.0	32859911
AllCCS	[M-H]-	168.7	32859911
AllCCS	[M+Na-2H]-	168.0	32859911
AllCCS	[M+HCOO]-	167.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenytoin methylcatechol	OC1=C(C=O)C=C(C=C1)C1(NC(=O)NC1=O)C1=CC=CC=C1	4251.6	Standard polar	33892256
Phenytoin methylcatechol	OC1=C(C=O)C=C(C=C1)C1(NC(=O)NC1=O)C1=CC=CC=C1	2953.3	Standard non polar	33892256
Phenytoin methylcatechol	OC1=C(C=O)C=C(C=C1)C1(NC(=O)NC1=O)C1=CC=CC=C1	2907.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenytoin methylcatechol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)NC2=O)C=C1C=O	3047.8	Semi standard non polar	33892256
Phenytoin methylcatechol,1TMS,isomer #2	C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=C(O)C(C=O)=C1	2856.3	Semi standard non polar	33892256
Phenytoin methylcatechol,1TMS,isomer #3	C[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O	2850.2	Semi standard non polar	33892256
Phenytoin methylcatechol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)C=C1C=O	2895.7	Semi standard non polar	33892256
Phenytoin methylcatechol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)C=C1C=O	2842.7	Standard non polar	33892256
Phenytoin methylcatechol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)C=C1C=O	4055.2	Standard polar	33892256
Phenytoin methylcatechol,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)C=C1C=O	2931.7	Semi standard non polar	33892256
Phenytoin methylcatechol,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)C=C1C=O	2802.6	Standard non polar	33892256
Phenytoin methylcatechol,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)C=C1C=O	3862.0	Standard polar	33892256
Phenytoin methylcatechol,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O	2537.3	Semi standard non polar	33892256
Phenytoin methylcatechol,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O	2811.4	Standard non polar	33892256
Phenytoin methylcatechol,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O	3555.3	Standard polar	33892256
Phenytoin methylcatechol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)C=C1C=O	2643.0	Semi standard non polar	33892256
Phenytoin methylcatechol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)C=C1C=O	2806.4	Standard non polar	33892256
Phenytoin methylcatechol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)C=C1C=O	3320.4	Standard polar	33892256
Phenytoin methylcatechol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)NC2=O)C=C1C=O	3308.2	Semi standard non polar	33892256
Phenytoin methylcatechol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=C(O)C(C=O)=C1	3153.7	Semi standard non polar	33892256
Phenytoin methylcatechol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O	3175.1	Semi standard non polar	33892256
Phenytoin methylcatechol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)C=C1C=O	3428.0	Semi standard non polar	33892256
Phenytoin methylcatechol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)C=C1C=O	3241.8	Standard non polar	33892256
Phenytoin methylcatechol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)C=C1C=O	4021.1	Standard polar	33892256
Phenytoin methylcatechol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1C=O	3452.0	Semi standard non polar	33892256
Phenytoin methylcatechol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1C=O	3219.7	Standard non polar	33892256
Phenytoin methylcatechol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1C=O	3924.4	Standard polar	33892256
Phenytoin methylcatechol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O	3101.0	Semi standard non polar	33892256
Phenytoin methylcatechol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O	3228.0	Standard non polar	33892256
Phenytoin methylcatechol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O	3576.2	Standard polar	33892256
Phenytoin methylcatechol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=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=C1C=O	3396.3	Semi standard non polar	33892256
Phenytoin methylcatechol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=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=C1C=O	3415.2	Standard non polar	33892256
Phenytoin methylcatechol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=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=C1C=O	3454.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin methylcatechol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0v00-0960000000-bda3f49ea38924bfc1bd	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin methylcatechol GC-MS (1 TMS) - 70eV, Positive	splash10-00b9-2893000000-5cfff8f48221b1f4f758	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin methylcatechol 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 methylcatechol 10V, Positive-QTOF	splash10-004j-0090000000-89e8077f74c6891cd4ac	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 20V, Positive-QTOF	splash10-004i-0190000000-ca80aa4f8cf0ad545b2a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 40V, Positive-QTOF	splash10-05fr-0940000000-00d5e69231c0bf46dd19	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 10V, Negative-QTOF	splash10-0002-0090000000-90d05301f1b239e4a5e6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 20V, Negative-QTOF	splash10-0fxw-3190000000-281651580bc4a38bea5e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 40V, Negative-QTOF	splash10-0udm-4920000000-05f9311da7a5c3b02614	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 10V, Positive-QTOF	splash10-0002-0090000000-0c95764557d19b6513e0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 20V, Positive-QTOF	splash10-004i-0390000000-885fed503b67c278c72a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 40V, Positive-QTOF	splash10-00fr-1790000000-54ce2dcc4b90f291fa63	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 10V, Negative-QTOF	splash10-0002-0090000000-8c0a37cb17704175d425	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 20V, Negative-QTOF	splash10-0007-9370000000-7802a8e4e264c3c4fc3a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 40V, Negative-QTOF	splash10-0006-9500000000-ccb684269530162f2746	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

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

131769979

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 methylcatechol (HMDB0060867)

MOL for HMDB0060867 (Phenytoin methylcatechol)

3D MOL for HMDB0060867 (Phenytoin methylcatechol)

3D SDF for HMDB0060867 (Phenytoin methylcatechol)

3D-SDF for HMDB0060867 (Phenytoin methylcatechol)

PDB for HMDB0060867 (Phenytoin methylcatechol)

3D PDB for HMDB0060867 (Phenytoin methylcatechol)

SMILES for HMDB0060867 (Phenytoin methylcatechol)

INCHI for HMDB0060867 (Phenytoin methylcatechol)

Structure for HMDB0060867 (Phenytoin methylcatechol)

3D Structure for HMDB0060867 (Phenytoin methylcatechol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra