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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:35:38 UTC

Update Date

2021-09-26 23:17:29 UTC

HMDB ID

HMDB0259746

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Valeroyl phenytoin

Description

2-hydroxy-1-pentanoyl-4,4-diphenyl-4,5-dihydro-1H-imidazol-5-one belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. Based on a literature review very few articles have been published on 2-hydroxy-1-pentanoyl-4,4-diphenyl-4,5-dihydro-1H-imidazol-5-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Valeroyl phenytoin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Valeroyl phenytoin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0259746
     RDKit          3D
Valeroyl phenytoin
 45 47  0  0  0  0  0  0  0  0999 V2000
    5.9857   -0.3157   -0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6683    1.0142   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4886    0.8587    0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2936    0.3861    0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963    0.2057    0.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1356    0.4182    2.1247 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8747   -0.2139    0.3157 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6849   -0.4875   -1.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6001   -0.3848   -1.9383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6606   -0.8833   -1.3024 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963   -0.4933   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9397    0.8856   -0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6452    1.9521    0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1840    3.2031    0.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9913    3.3475   -1.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2746    2.2480   -1.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7440    1.0170   -1.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4949   -1.4313    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3249   -1.1757    1.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3724   -2.0285    1.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5651   -3.1566    0.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7199   -3.3936   -0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6754   -2.5482   -0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3777   -0.4484    0.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851   -0.5909    2.1521 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5775   -1.1757   -0.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0854   -0.4544   -0.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5255   -0.3561   -1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5432    1.4163    0.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3833    1.7929   -0.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978    0.1924    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2383    1.8728    1.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    1.0669   -0.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6396   -0.5837   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320   -1.3534   -2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0086    1.8246    1.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    4.0440    0.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3885    4.3283   -1.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9046    2.3666   -2.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9526    0.1627   -2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -0.2981    1.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0367   -1.8413    2.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3721   -3.8778    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8668   -4.2878   -0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0604   -2.8237   -1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 11 24  1  0
 24 25  2  0
 24  7  1  0
 17 12  1  0
 23 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
 10 35  1  0
 13 36  1  0
 14 37  1  0
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 16 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
M  END


  Mrv1652309122100352D          

 25 27  0  0  0  0            999 V2000
    0.0221   -4.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365   -5.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4510   -4.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1655   -5.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799   -4.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799   -3.8520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5944   -5.0895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3481   -4.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5196   -3.9470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9001   -5.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4876   -6.0815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6806   -5.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0676   -6.4620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3920   -4.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0644   -3.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5562   -3.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3758   -3.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7034   -4.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2115   -4.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6573   -5.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3196   -5.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0767   -5.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1716   -6.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5092   -6.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521   -6.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 10 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
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259746

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC(=O)N1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20N2O3/c1-2-3-14-17(23)22-18(24)20(21-19(22)25,15-10-6-4-7-11-15)16-12-8-5-9-13-16/h4-13H,2-3,14H2,1H3,(H,21,25)

> <INCHI_KEY>
DYVNLCJHGUOASO-UHFFFAOYSA-N

> <FORMULA>
C20H20N2O3

> <MOLECULAR_WEIGHT>
336.391

> <EXACT_MASS>
336.147392512

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
36.161690611600925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-pentanoyl-5,5-diphenylimidazolidine-2,4-dione

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
3.726201863333333

> <ALOGPS_LOGS>
-4.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.478150333890264

> <JCHEM_POLAR_SURFACE_AREA>
66.48

> <JCHEM_REFRACTIVITY>
93.57710000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-pentanoyl-5,5-diphenylimidazolidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259746
     RDKit          3D
Valeroyl phenytoin
 45 47  0  0  0  0  0  0  0  0999 V2000
    5.9857   -0.3157   -0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6683    1.0142   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4886    0.8587    0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2936    0.3861    0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963    0.2057    0.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1356    0.4182    2.1247 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8747   -0.2139    0.3157 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6849   -0.4875   -1.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6001   -0.3848   -1.9383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6606   -0.8833   -1.3024 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963   -0.4933   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9397    0.8856   -0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6452    1.9521    0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1840    3.2031    0.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9913    3.3475   -1.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2746    2.2480   -1.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7440    1.0170   -1.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4949   -1.4313    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3249   -1.1757    1.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3724   -2.0285    1.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5651   -3.1566    0.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7199   -3.3936   -0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6754   -2.5482   -0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3777   -0.4484    0.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851   -0.5909    2.1521 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5775   -1.1757   -0.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0854   -0.4544   -0.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5255   -0.3561   -1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5432    1.4163    0.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3833    1.7929   -0.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978    0.1924    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2383    1.8728    1.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    1.0669   -0.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6396   -0.5837   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320   -1.3534   -2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0086    1.8246    1.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    4.0440    0.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3885    4.3283   -1.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9046    2.3666   -2.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9526    0.1627   -2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -0.2981    1.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0367   -1.8413    2.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3721   -3.8778    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8668   -4.2878   -0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0604   -2.8237   -1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 11 24  1  0
 24 25  2  0
 24  7  1  0
 17 12  1  0
 23 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
 10 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  C   UNK     0       0.041  -8.730   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.375  -9.500   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.709  -8.730   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.042  -9.500   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.376  -8.730   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.376  -7.190   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       6.710  -9.500   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       8.116  -8.874   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.437  -7.368   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.147 -10.018   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       8.377 -11.352   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.871 -11.032   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.726 -12.062   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.065  -8.782   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.453  -7.369   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.372  -6.132   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.901  -6.309   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.513  -7.723   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.595  -8.959   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.560 -10.630   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.797  -9.712   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.210 -10.323   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.387 -11.853   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.151 -12.771   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.737 -12.160   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   14   20                                             
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12                                                            
CONECT   14   10   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   10   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0259746
HETATM    1  C1  UNL     1       5.986  -0.316  -0.716  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.668   1.014  -0.057  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.489   0.859   0.883  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.294   0.386   0.066  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.096   0.206   0.897  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.136   0.418   2.125  1.00  0.00           O  
HETATM    7  N1  UNL     1       0.875  -0.214   0.316  1.00  0.00           N  
HETATM    8  C6  UNL     1       0.685  -0.488  -1.067  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.600  -0.385  -1.938  1.00  0.00           O  
HETATM   10  N2  UNL     1      -0.661  -0.883  -1.302  1.00  0.00           N  
HETATM   11  C7  UNL     1      -1.396  -0.493  -0.134  1.00  0.00           C  
HETATM   12  C8  UNL     1      -1.940   0.886  -0.406  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.645   1.952   0.416  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.184   3.203   0.107  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.991   3.348  -1.000  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.275   2.248  -1.818  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.744   1.017  -1.515  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.495  -1.431   0.178  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.325  -1.176   1.238  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.372  -2.029   1.576  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.565  -3.157   0.812  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.720  -3.394  -0.248  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.675  -2.548  -0.589  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.378  -0.448   0.932  1.00  0.00           C  
HETATM   25  O3  UNL     1      -0.585  -0.591   2.152  1.00  0.00           O  
HETATM   26  H1  UNL     1       5.578  -1.176  -0.128  1.00  0.00           H  
HETATM   27  H2  UNL     1       7.085  -0.454  -0.734  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.526  -0.356  -1.714  1.00  0.00           H  
HETATM   29  H4  UNL     1       6.543   1.416   0.478  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.383   1.793  -0.796  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.698   0.192   1.729  1.00  0.00           H  
HETATM   32  H7  UNL     1       4.238   1.873   1.284  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.136   1.067  -0.792  1.00  0.00           H  
HETATM   34  H9  UNL     1       3.640  -0.584  -0.397  1.00  0.00           H  
HETATM   35  H10 UNL     1      -0.932  -1.353  -2.195  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.009   1.825   1.285  1.00  0.00           H  
HETATM   37  H12 UNL     1      -1.966   4.044   0.733  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.389   4.328  -1.205  1.00  0.00           H  
HETATM   39  H14 UNL     1      -3.905   2.367  -2.680  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.953   0.163  -2.134  1.00  0.00           H  
HETATM   41  H16 UNL     1      -3.215  -0.298   1.875  1.00  0.00           H  
HETATM   42  H17 UNL     1      -5.037  -1.841   2.410  1.00  0.00           H  
HETATM   43  H18 UNL     1      -5.372  -3.878   1.018  1.00  0.00           H  
HETATM   44  H19 UNL     1      -3.867  -4.288  -0.858  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.060  -2.824  -1.446  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6    6    7
CONECT    7    8   24
CONECT    8    9    9   10
CONECT   10   11   35
CONECT   11   12   18   24
CONECT   12   13   13   17
CONECT   13   14   36
CONECT   14   15   15   37
CONECT   15   16   38
CONECT   16   17   17   39
CONECT   17   40
CONECT   18   19   19   23
CONECT   19   20   41
CONECT   20   21   21   42
CONECT   21   22   43
CONECT   22   23   23   44
CONECT   23   45
CONECT   24   25   25
END

HMDB0259746
     RDKit          3D
Valeroyl phenytoin
 45 47  0  0  0  0  0  0  0  0999 V2000
    5.9857   -0.3157   -0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6683    1.0142   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4886    0.8587    0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2936    0.3861    0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963    0.2057    0.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1356    0.4182    2.1247 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8747   -0.2139    0.3157 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6849   -0.4875   -1.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6001   -0.3848   -1.9383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6606   -0.8833   -1.3024 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963   -0.4933   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9397    0.8856   -0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6452    1.9521    0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1840    3.2031    0.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9913    3.3475   -1.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2746    2.2480   -1.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7440    1.0170   -1.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4949   -1.4313    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3249   -1.1757    1.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3724   -2.0285    1.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5651   -3.1566    0.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7199   -3.3936   -0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6754   -2.5482   -0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3777   -0.4484    0.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851   -0.5909    2.1521 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5775   -1.1757   -0.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0854   -0.4544   -0.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5255   -0.3561   -1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5432    1.4163    0.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3833    1.7929   -0.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978    0.1924    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2383    1.8728    1.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    1.0669   -0.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6396   -0.5837   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320   -1.3534   -2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0086    1.8246    1.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    4.0440    0.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3885    4.3283   -1.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9046    2.3666   -2.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9526    0.1627   -2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -0.2981    1.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0367   -1.8413    2.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3721   -3.8778    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8668   -4.2878   -0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0604   -2.8237   -1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 11 24  1  0
 24 25  2  0
 24  7  1  0
 17 12  1  0
 23 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
 10 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Pentanoyl-5,5-diphenylhydantoin	MeSH
Valeroyl DPH	MeSH
VADPH	MeSH

Chemical Formula

C₂₀H₂₀N₂O₃

Average Molecular Weight

336.391

Monoisotopic Molecular Weight

336.147392512

IUPAC Name

3-pentanoyl-5,5-diphenylimidazolidine-2,4-dione

Traditional Name

3-pentanoyl-5,5-diphenylimidazolidine-2,4-dione

CAS Registry Number

Not Available

SMILES

CCCCC(=O)N1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C20H20N2O3/c1-2-3-14-17(23)22-18(24)20(21-19(22)25,15-10-6-4-7-11-15)16-12-8-5-9-13-16/h4-13H,2-3,14H2,1H3,(H,21,25)

InChI Key

DYVNLCJHGUOASO-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
N-acyl urea
Ureide
Monocyclic benzene moiety
Benzenoid
Carboxylic acid imide, n-substituted
Carboxylic acid imide
Dicarboximide
Urea
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organonitrogen 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 (PMID: 31557052)

Process

Not Available

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
logP	3.47	ALOGPS
logP	3.73	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	10.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.58 m³·mol⁻¹	ChemAxon
Polarizability	36.16 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
AllCCS	[M+H]+	180.356	32859911
AllCCS	[M+H-H2O]+	177.231	32859911
AllCCS	[M+Na]+	184.076	32859911
AllCCS	[M+NH4]+	183.246	32859911
AllCCS	[M-H]-	183.689	32859911
AllCCS	[M+Na-2H]-	183.529	32859911
AllCCS	[M+HCOO]-	183.494	32859911
DeepCCS	[M+H]+	187.2	30932474
DeepCCS	[M-H]-	184.489	30932474
DeepCCS	[M-2H]-	219.134	30932474
DeepCCS	[M+Na]+	194.942	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Valeroyl phenytoin	CCCCC(=O)N1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1	3720.0	Standard polar	33892256
Valeroyl phenytoin	CCCCC(=O)N1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1	2643.8	Standard non polar	33892256
Valeroyl phenytoin	CCCCC(=O)N1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1	2625.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Valeroyl phenytoin,1TMS,isomer #1	CCCCC(=O)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2576.2	Semi standard non polar	33892256
Valeroyl phenytoin,1TMS,isomer #1	CCCCC(=O)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2512.7	Standard non polar	33892256
Valeroyl phenytoin,1TMS,isomer #1	CCCCC(=O)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	3543.9	Standard polar	33892256
Valeroyl phenytoin,1TBDMS,isomer #1	CCCCC(=O)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2837.5	Semi standard non polar	33892256
Valeroyl phenytoin,1TBDMS,isomer #1	CCCCC(=O)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2759.5	Standard non polar	33892256
Valeroyl phenytoin,1TBDMS,isomer #1	CCCCC(=O)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	3552.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Valeroyl phenytoin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0lgi-6951000000-e30dfc09f982ea69051c	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valeroyl phenytoin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

2283331

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Valeroyl phenytoin (HMDB0259746)

MOL for HMDB0259746 (Valeroyl phenytoin)

3D MOL for HMDB0259746 (Valeroyl phenytoin)

3D SDF for HMDB0259746 (Valeroyl phenytoin)

3D-SDF for HMDB0259746 (Valeroyl phenytoin)

PDB for HMDB0259746 (Valeroyl phenytoin)

3D PDB for HMDB0259746 (Valeroyl phenytoin)

SMILES for HMDB0259746 (Valeroyl phenytoin)

INCHI for HMDB0259746 (Valeroyl phenytoin)

Structure for HMDB0259746 (Valeroyl phenytoin)

3D Structure for HMDB0259746 (Valeroyl phenytoin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra