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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:04:21 UTC

Update Date

2021-09-14 15:48:01 UTC

HMDB ID

HMDB0060865

Secondary Accession Numbers

HMDB60865

Metabolite Identification

Common Name

Phenytoin catechol

Description

Phenytoin catechol, also known as 5-DHPPH, 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 catechol is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, phenytoin catechol participates in a number of enzymatic reactions. In particular, phenytoin catechol can be biosynthesized from hydroxyphenytoin; which is mediated by the enzymes cytochrome P450 2C9, cytochrome P450 2C19, and cytochrome P450 3A4. In addition, phenytoin catechol and S-adenosylmethionine can be converted into phenytoin methylcatechol and S-adenosylhomocysteine; which is catalyzed by the enzyme catechol O-methyltransferase. Phenytoin catechol is a metabolite of phenytoin. In humans, phenytoin catechol 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 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.

Structure

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

HMDB0060865
     RDKit          3D
Phenytoin catechol
 33 35  0  0  0  0  0  0  0  0999 V2000
   -2.6816    3.3061   -0.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7229    2.5786   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209    2.0787   -1.8371 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3156    1.2861   -1.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4496    1.0616   -2.7792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312    0.8246   -0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3322   -0.1367   -0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1398    0.0401    1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1661   -0.8038    1.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735   -1.8950    0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6117   -2.1452   -0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5918   -1.2478   -0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0603    0.3513    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4980    0.6227    1.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7386    0.1539    1.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5492   -0.5809    0.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035   -1.0412    1.3339 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1109   -0.8486   -0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8926   -1.5775   -1.2461 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8851   -0.3834   -0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6398    2.0713    0.2525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0890    2.2199   -2.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9745    0.9007    1.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7848   -0.6277    2.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1674   -2.5996    0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -2.9990   -1.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9609   -1.4007   -1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9361    1.1896    2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1018    0.3618    2.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1343   -0.8531    2.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5788   -1.7798   -2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5906   -0.6428   -1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493    2.5159    1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
  6 21  1  0
 21  2  1  0
 12  7  1  0
 20 13  1  0
  3 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
M  END


  Mrv0541 07041312042D          

 21 23  0  0  0  0            999 V2000
   -1.0241    1.3951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4720    0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3349    0.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5899    1.7382    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060865

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H12N2O4/c18-11-7-6-10(8-12(11)19)15(9-4-2-1-3-5-9)13(20)16-14(21)17-15/h1-8,18-19H,(H2,16,17,20,21)

> <INCHI_KEY>
WWEKVOUOQUHVHS-UHFFFAOYSA-N

> <FORMULA>
C15H12N2O4

> <MOLECULAR_WEIGHT>
284.2668

> <EXACT_MASS>
284.079706882

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.35998364533144

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(3,4-dihydroxyphenyl)-5-phenylimidazolidine-2,4-dione

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
1.5407897373333328

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.660150193791496

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.998167074532128

> <JCHEM_PKA_STRONGEST_BASIC>
-6.290625068155767

> <JCHEM_POLAR_SURFACE_AREA>
98.66

> <JCHEM_REFRACTIVITY>
74.14410000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(3,4-dihydroxyphenyl)-5-phenylimidazolidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060865
     RDKit          3D
Phenytoin catechol
 33 35  0  0  0  0  0  0  0  0999 V2000
   -2.6816    3.3061   -0.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7229    2.5786   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209    2.0787   -1.8371 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3156    1.2861   -1.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4496    1.0616   -2.7792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312    0.8246   -0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3322   -0.1367   -0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1398    0.0401    1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1661   -0.8038    1.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735   -1.8950    0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6117   -2.1452   -0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5918   -1.2478   -0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0603    0.3513    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4980    0.6227    1.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7386    0.1539    1.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5492   -0.5809    0.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035   -1.0412    1.3339 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1109   -0.8486   -0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8926   -1.5775   -1.2461 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8851   -0.3834   -0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6398    2.0713    0.2525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0890    2.2199   -2.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9745    0.9007    1.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7848   -0.6277    2.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1674   -2.5996    0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -2.9990   -1.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9609   -1.4007   -1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9361    1.1896    2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1018    0.3618    2.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1343   -0.8531    2.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5788   -1.7798   -2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5906   -0.6428   -1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493    2.5159    1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
  6 21  1  0
 21  2  1  0
 12  7  1  0
 20 13  1  0
  3 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  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  O   UNK     0       1.101   3.245   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.656   0.636   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.180  -0.829   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.326  -1.149   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.357  -0.005   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.210  -1.973   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.456  -2.879   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.980  -4.343   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.885  -5.589   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       1.440  -4.343   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       0.964  -2.879   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.500  -2.403   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.241  -0.829   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.765   0.636   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.795   1.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.302   1.460   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.778  -0.005   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.747  -1.149   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    2                                                       
CONECT    9    6   10   14   16                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16    9   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0060865
HETATM    1  O1  UNL     1      -2.682   3.306  -0.156  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.723   2.579  -0.503  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.521   2.079  -1.837  1.00  0.00           N  
HETATM    4  C2  UNL     1      -0.316   1.286  -1.825  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.450   1.062  -2.779  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.231   0.825  -0.422  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.332  -0.137  -0.098  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.140   0.040   1.004  1.00  0.00           C  
HETATM    9  C6  UNL     1      -3.166  -0.804   1.362  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.374  -1.895   0.536  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.612  -2.145  -0.585  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.592  -1.248  -0.883  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.060   0.351   0.028  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.498   0.623   1.302  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.739   0.154   1.716  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.549  -0.581   0.880  1.00  0.00           C  
HETATM   17  O3  UNL     1       4.803  -1.041   1.334  1.00  0.00           O  
HETATM   18  C14 UNL     1       3.111  -0.849  -0.386  1.00  0.00           C  
HETATM   19  O4  UNL     1       3.893  -1.578  -1.246  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.885  -0.383  -0.788  1.00  0.00           C  
HETATM   21  N2  UNL     1      -0.640   2.071   0.253  1.00  0.00           N  
HETATM   22  H1  UNL     1      -2.089   2.220  -2.695  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.974   0.901   1.652  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.785  -0.628   2.246  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.167  -2.600   0.762  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.776  -2.999  -1.228  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.961  -1.401  -1.758  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.936   1.190   2.039  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.102   0.362   2.728  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.134  -0.853   2.255  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.579  -1.780  -2.185  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.591  -0.643  -1.818  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.249   2.516   1.095  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   13   21
CONECT    7    8    8   12
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   27
CONECT   13   14   14   20
CONECT   14   15   28
CONECT   15   16   16   29
CONECT   16   17   18
CONECT   17   30
CONECT   18   19   20   20
CONECT   19   31
CONECT   20   32
CONECT   21   33
END

HMDB0060865
     RDKit          3D
Phenytoin catechol
 33 35  0  0  0  0  0  0  0  0999 V2000
   -2.6816    3.3061   -0.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7229    2.5786   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209    2.0787   -1.8371 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3156    1.2861   -1.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4496    1.0616   -2.7792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312    0.8246   -0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3322   -0.1367   -0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1398    0.0401    1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1661   -0.8038    1.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735   -1.8950    0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6117   -2.1452   -0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5918   -1.2478   -0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0603    0.3513    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4980    0.6227    1.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7386    0.1539    1.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5492   -0.5809    0.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035   -1.0412    1.3339 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1109   -0.8486   -0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8926   -1.5775   -1.2461 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8851   -0.3834   -0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6398    2.0713    0.2525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0890    2.2199   -2.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9745    0.9007    1.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7848   -0.6277    2.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1674   -2.5996    0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -2.9990   -1.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9609   -1.4007   -1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9361    1.1896    2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1018    0.3618    2.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1343   -0.8531    2.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5788   -1.7798   -2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5906   -0.6428   -1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493    2.5159    1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
  6 21  1  0
 21  2  1  0
 12  7  1  0
 20 13  1  0
  3 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-DHPPH	HMDB
5-(3,4-Dihydroxyphenyl)-5-phenylhydantoin	MeSH

Chemical Formula

C₁₅H₁₂N₂O₄

Average Molecular Weight

284.2668

Monoisotopic Molecular Weight

284.079706882

IUPAC Name

5-(3,4-dihydroxyphenyl)-5-phenylimidazolidine-2,4-dione

Traditional Name

5-(3,4-dihydroxyphenyl)-5-phenylimidazolidine-2,4-dione

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H12N2O4/c18-11-7-6-10(8-12(11)19)15(9-4-2-1-3-5-9)13(20)16-14(21)17-15/h1-8,18-19H,(H2,16,17,20,21)

InChI Key

WWEKVOUOQUHVHS-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
Catechol
5-monosubstituted hydantoin
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
N-acyl urea
Phenol
Ureide
Monocyclic benzene moiety
Benzenoid
Dicarboximide
Carbonic acid derivative
Urea
Azacycle
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen 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: HMDB0060865)

Organ

Kidney (HMDB: HMDB0060865)
Liver (HMDB: HMDB0060865)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060865)

Cellular substructure

Cytoplasm (HMDB: HMDB0060865)

Source

Endogenous

Endogenous (HMDB: HMDB0060865)

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	0.31 g/L	ALOGPS
logP	1.5	ALOGPS
logP	1.54	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	98.66 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.14 m³·mol⁻¹	ChemAxon
Polarizability	27.36 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]+	167.103	31661259
DarkChem	[M-H]-	162.833	31661259
DeepCCS	[M+H]+	170.074	30932474
DeepCCS	[M-H]-	167.716	30932474
DeepCCS	[M-2H]-	201.135	30932474
DeepCCS	[M+Na]+	176.362	30932474
AllCCS	[M+H]+	164.8	32859911
AllCCS	[M+H-H2O]+	161.0	32859911
AllCCS	[M+NH4]+	168.3	32859911
AllCCS	[M+Na]+	169.3	32859911
AllCCS	[M-H]-	165.5	32859911
AllCCS	[M+Na-2H]-	164.9	32859911
AllCCS	[M+HCOO]-	164.3	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.	4.54 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8199 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.03 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1687.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	252.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	123.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	95.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	431.4 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	469.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	104.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	848.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	378.0 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	1236.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	298.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	346.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	166.8 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	142.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenytoin catechol	OC1=C(O)C=C(C=C1)C1(NC(=O)NC1=O)C1=CC=CC=C1	4261.9	Standard polar	33892256
Phenytoin catechol	OC1=C(O)C=C(C=C1)C1(NC(=O)NC1=O)C1=CC=CC=C1	2947.1	Standard non polar	33892256
Phenytoin catechol	OC1=C(O)C=C(C=C1)C1(NC(=O)NC1=O)C1=CC=CC=C1	2905.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenytoin catechol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)NC2=O)C=C1O	2925.0	Semi standard non polar	33892256
Phenytoin catechol,1TMS,isomer #2	C[Si](C)(C)OC1=CC(C2(C3=CC=CC=C3)NC(=O)NC2=O)=CC=C1O	2923.5	Semi standard non polar	33892256
Phenytoin catechol,1TMS,isomer #3	C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=C(O)C(O)=C1	2788.8	Semi standard non polar	33892256
Phenytoin catechol,1TMS,isomer #4	C[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=C(O)C(O)=C2)C1=O	2782.6	Semi standard non polar	33892256
Phenytoin catechol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)NC2=O)C=C1O[Si](C)(C)C	2982.4	Semi standard non polar	33892256
Phenytoin catechol,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)C=C1O	2752.4	Semi standard non polar	33892256
Phenytoin catechol,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)C=C1O	2800.6	Semi standard non polar	33892256
Phenytoin catechol,2TMS,isomer #4	C[Si](C)(C)OC1=CC(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)=CC=C1O	2764.9	Semi standard non polar	33892256
Phenytoin catechol,2TMS,isomer #5	C[Si](C)(C)OC1=CC(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)=CC=C1O	2828.2	Semi standard non polar	33892256
Phenytoin catechol,2TMS,isomer #6	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=C(O)C(O)=C2)C1=O	2502.4	Semi standard non polar	33892256
Phenytoin catechol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)C=C1O[Si](C)(C)C	2790.3	Semi standard non polar	33892256
Phenytoin catechol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)C=C1O[Si](C)(C)C	2757.7	Standard non polar	33892256
Phenytoin catechol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)C=C1O[Si](C)(C)C	3783.8	Standard polar	33892256
Phenytoin catechol,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)C=C1O[Si](C)(C)C	2878.5	Semi standard non polar	33892256
Phenytoin catechol,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)C=C1O[Si](C)(C)C	2687.8	Standard non polar	33892256
Phenytoin catechol,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)C=C1O[Si](C)(C)C	3624.6	Standard polar	33892256
Phenytoin catechol,3TMS,isomer #3	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=C1O	2516.3	Semi standard non polar	33892256
Phenytoin catechol,3TMS,isomer #3	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=C1O	2707.1	Standard non polar	33892256
Phenytoin catechol,3TMS,isomer #3	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=C1O	3265.8	Standard polar	33892256
Phenytoin catechol,3TMS,isomer #4	C[Si](C)(C)OC1=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=CC=C1O	2517.6	Semi standard non polar	33892256
Phenytoin catechol,3TMS,isomer #4	C[Si](C)(C)OC1=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=CC=C1O	2714.1	Standard non polar	33892256
Phenytoin catechol,3TMS,isomer #4	C[Si](C)(C)OC1=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=CC=C1O	3258.0	Standard polar	33892256
Phenytoin catechol,4TMS,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=C1O[Si](C)(C)C	2607.3	Semi standard non polar	33892256
Phenytoin catechol,4TMS,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=C1O[Si](C)(C)C	2721.5	Standard non polar	33892256
Phenytoin catechol,4TMS,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=C1O[Si](C)(C)C	3072.9	Standard polar	33892256
Phenytoin catechol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)NC2=O)C=C1O	3198.6	Semi standard non polar	33892256
Phenytoin catechol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(C2(C3=CC=CC=C3)NC(=O)NC2=O)=CC=C1O	3183.2	Semi standard non polar	33892256
Phenytoin catechol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=C(O)C(O)=C1	3102.6	Semi standard non polar	33892256
Phenytoin catechol,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=C(O)C(O)=C2)C1=O	3137.1	Semi standard non polar	33892256
Phenytoin catechol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)NC2=O)C=C1O[Si](C)(C)C(C)(C)C	3429.6	Semi standard non polar	33892256
Phenytoin catechol,2TBDMS,isomer #2	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=C1O	3312.4	Semi standard non polar	33892256
Phenytoin catechol,2TBDMS,isomer #3	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=C1O	3365.9	Semi standard non polar	33892256
Phenytoin catechol,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)=CC=C1O	3296.2	Semi standard non polar	33892256
Phenytoin catechol,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)=CC=C1O	3373.1	Semi standard non polar	33892256
Phenytoin catechol,2TBDMS,isomer #6	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(O)=C2)C1=O	3086.5	Semi standard non polar	33892256
Phenytoin catechol,3TBDMS,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=C1O[Si](C)(C)C(C)(C)C	3473.4	Semi standard non polar	33892256
Phenytoin catechol,3TBDMS,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=C1O[Si](C)(C)C(C)(C)C	3324.3	Standard non polar	33892256
Phenytoin catechol,3TBDMS,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=C1O[Si](C)(C)C(C)(C)C	3854.9	Standard polar	33892256
Phenytoin catechol,3TBDMS,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=C1O[Si](C)(C)C(C)(C)C	3563.0	Semi standard non polar	33892256
Phenytoin catechol,3TBDMS,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=C1O[Si](C)(C)C(C)(C)C	3315.9	Standard non polar	33892256
Phenytoin catechol,3TBDMS,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=C1O[Si](C)(C)C(C)(C)C	3804.3	Standard polar	33892256
Phenytoin catechol,3TBDMS,isomer #3	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=C1O	3292.9	Semi standard non polar	33892256
Phenytoin catechol,3TBDMS,isomer #3	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=C1O	3336.4	Standard non polar	33892256
Phenytoin catechol,3TBDMS,isomer #3	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=C1O	3430.6	Standard polar	33892256
Phenytoin catechol,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=CC=C1O	3289.7	Semi standard non polar	33892256
Phenytoin catechol,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=CC=C1O	3338.6	Standard non polar	33892256
Phenytoin catechol,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=CC=C1O	3423.6	Standard polar	33892256
Phenytoin catechol,4TBDMS,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=C1O[Si](C)(C)C(C)(C)C	3484.2	Semi standard non polar	33892256
Phenytoin catechol,4TBDMS,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=C1O[Si](C)(C)C(C)(C)C	3517.2	Standard non polar	33892256
Phenytoin catechol,4TBDMS,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=C1O[Si](C)(C)C(C)(C)C	3340.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin catechol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fca-0940000000-a7ccf34eb5ce4d22abc2	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin catechol GC-MS (2 TMS) - 70eV, Positive	splash10-004i-2419100000-7f77171a77be7bd65840	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenytoin catechol 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 catechol 10V, Positive-QTOF	splash10-01p9-0090000000-dad91da97b1e4e52742e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin catechol 20V, Positive-QTOF	splash10-03di-0390000000-8a594c3506ebef20432b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin catechol 40V, Positive-QTOF	splash10-0a4i-0900000000-cd892d8939b9b1ac2a62	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin catechol 10V, Negative-QTOF	splash10-001i-0090000000-54cf9fb76a7077ad6ea7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin catechol 20V, Negative-QTOF	splash10-000x-3190000000-2627b89d3e0e646a4426	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin catechol 40V, Negative-QTOF	splash10-0udl-5920000000-d0a1000f2d83b7ff28e0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin catechol 10V, Positive-QTOF	splash10-000i-0090000000-5a6646808a09b093adb4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin catechol 20V, Positive-QTOF	splash10-01p2-0590000000-dd5c6ce0f3b3faf31495	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin catechol 40V, Positive-QTOF	splash10-03di-1970000000-8104dfa89c4b45f0a4d7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin catechol 10V, Negative-QTOF	splash10-001i-0090000000-d9e4a73a97cc3e5ef1ca	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin catechol 20V, Negative-QTOF	splash10-06u6-7890000000-6abd1c0823b37ab71f65	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenytoin catechol 40V, Negative-QTOF	splash10-006x-7900000000-832630454446d363e341	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

169703

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 catechol (HMDB0060865)

MOL for HMDB0060865 (Phenytoin catechol)

3D MOL for HMDB0060865 (Phenytoin catechol)

3D SDF for HMDB0060865 (Phenytoin catechol)

3D-SDF for HMDB0060865 (Phenytoin catechol)

PDB for HMDB0060865 (Phenytoin catechol)

3D PDB for HMDB0060865 (Phenytoin catechol)

SMILES for HMDB0060865 (Phenytoin catechol)

INCHI for HMDB0060865 (Phenytoin catechol)

Structure for HMDB0060865 (Phenytoin catechol)

3D Structure for HMDB0060865 (Phenytoin catechol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra