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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:50:30 UTC

Update Date

2021-09-26 22:54:28 UTC

HMDB ID

HMDB0245789

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione

Description

3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione, also known as 3-(hydroxymethyl)-5,5-diphenylhydantoin, 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 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3-(hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione 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

HMDB0245789
     RDKit          3D
3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.2258    0.3963    1.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3363   -0.0139    1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9464   -0.2471    1.3995 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1904   -0.2737    0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9854   -1.1419    0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5598   -1.3418    1.5849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6691   -2.1429    1.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2554   -2.7841    0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6995   -2.6003   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5969   -1.8015   -0.7172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2125    1.1342   -0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2797    1.6326   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561    2.9361   -1.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9683    3.7503   -0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8956    3.2358    0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    1.9361    0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2011   -0.7686   -0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9924   -1.4442   -1.8023 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -0.3405   -0.3094 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6476   -0.3026   -1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3830   -1.4687   -1.1729 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6783   -0.3551    2.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1772   -0.8748    2.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1063   -2.2893    2.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1196   -3.4137    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1471   -3.0956   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2295   -1.6975   -1.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0311    0.9814   -2.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6994    3.3036   -2.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2617    4.7715   -0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422    3.8786    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4688    1.5356    1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3494   -0.0500   -2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2786    0.5668   -0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9549   -1.6111   -0.4030 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19  2  1  0
 10  5  1  0
 16 11  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 20 33  1  0
 20 34  1  0
 21 35  1  0
M  END

  Mrv1652309112100502D          

 21 23  0  0  0  0            999 V2000
   -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
    0.8870    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6361   -1.2872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -2.3268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7716   -2.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2866   -2.9942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5166   -1.5422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815   -2.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9020   -2.9080    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  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  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  2  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 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>
HMDB0245789

> <DATABASE_NAME>
hmdb

> <SMILES>
OCN1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14N2O3/c19-11-18-14(20)16(17-15(18)21,12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,19H,11H2,(H,17,21)

> <INCHI_KEY>
QQBKLRXLVRDKEB-UHFFFAOYSA-N

> <FORMULA>
C16H14N2O3

> <MOLECULAR_WEIGHT>
282.299

> <EXACT_MASS>
282.100442319

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.574732222063474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.791595376666667

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.104566592566204

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.550207951745117

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2847062695108873

> <JCHEM_POLAR_SURFACE_AREA>
69.64

> <JCHEM_REFRACTIVITY>
76.1808

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenytoin,3-hydroxymethyl

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245789
     RDKit          3D
3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.2258    0.3963    1.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3363   -0.0139    1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9464   -0.2471    1.3995 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1904   -0.2737    0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9854   -1.1419    0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5598   -1.3418    1.5849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6691   -2.1429    1.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2554   -2.7841    0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6995   -2.6003   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5969   -1.8015   -0.7172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2125    1.1342   -0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2797    1.6326   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561    2.9361   -1.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9683    3.7503   -0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8956    3.2358    0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    1.9361    0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2011   -0.7686   -0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9924   -1.4442   -1.8023 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -0.3405   -0.3094 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6476   -0.3026   -1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3830   -1.4687   -1.1729 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6783   -0.3551    2.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1772   -0.8748    2.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1063   -2.2893    2.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1196   -3.4137    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1471   -3.0956   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2295   -1.6975   -1.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0311    0.9814   -2.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6994    3.3036   -2.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2617    4.7715   -0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422    3.8786    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4688    1.5356    1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3494   -0.0500   -2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2786    0.5668   -0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9549   -1.6111   -0.4030 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19  2  1  0
 10  5  1  0
 16 11  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 20 33  1  0
 20 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -0.881   1.460   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.625   1.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.656   0.636   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.180  -0.829   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.327  -1.149   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.357  -0.005   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.210  -1.974   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.456  -2.879   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.921  -2.403   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       2.980  -4.343   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.440  -4.343   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.535  -5.589   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       0.964  -2.879   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       3.885  -5.589   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.417  -5.428   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    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8   13   16                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7                                                       
CONECT   14   10   15                                                       
CONECT   15   14                                                            
CONECT   16    7   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    HMDB0245789
HETATM    1  O1  UNL     1       3.226   0.396   1.809  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.336  -0.014   1.054  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.946  -0.247   1.400  1.00  0.00           N  
HETATM    4  C2  UNL     1       0.190  -0.274   0.159  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.985  -1.142   0.334  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.560  -1.342   1.585  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.669  -2.143   1.793  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.255  -2.784   0.742  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.700  -2.600  -0.524  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.597  -1.801  -0.717  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.213   1.134  -0.136  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.280   1.633  -1.421  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.656   2.936  -1.657  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.968   3.750  -0.603  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.896   3.236   0.670  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.523   1.936   0.947  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.201  -0.769  -0.776  1.00  0.00           C  
HETATM   18  O2  UNL     1       0.992  -1.444  -1.802  1.00  0.00           O  
HETATM   19  N2  UNL     1       2.500  -0.341  -0.309  1.00  0.00           N  
HETATM   20  C16 UNL     1       3.648  -0.303  -1.149  1.00  0.00           C  
HETATM   21  O3  UNL     1       4.383  -1.469  -1.173  1.00  0.00           O  
HETATM   22  H1  UNL     1       0.678  -0.355   2.392  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.177  -0.875   2.476  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.106  -2.289   2.779  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.120  -3.414   0.878  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.147  -3.096  -1.359  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.229  -1.697  -1.719  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.031   0.981  -2.246  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.699   3.304  -2.694  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.262   4.772  -0.806  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.142   3.879   1.508  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.469   1.536   1.967  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.349  -0.050  -2.183  1.00  0.00           H  
HETATM   34  H13 UNL     1       4.279   0.567  -0.816  1.00  0.00           H  
HETATM   35  H14 UNL     1       4.955  -1.611  -0.403  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4   22
CONECT    4    5   11   17
CONECT    5    6    6   10
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   27
CONECT   11   12   12   16
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15   30
CONECT   15   16   16   31
CONECT   16   32
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   21   33   34
CONECT   21   35
END

HMDB0245789
     RDKit          3D
3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.2258    0.3963    1.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3363   -0.0139    1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9464   -0.2471    1.3995 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1904   -0.2737    0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9854   -1.1419    0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5598   -1.3418    1.5849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6691   -2.1429    1.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2554   -2.7841    0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6995   -2.6003   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5969   -1.8015   -0.7172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2125    1.1342   -0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2797    1.6326   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561    2.9361   -1.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9683    3.7503   -0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8956    3.2358    0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    1.9361    0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2011   -0.7686   -0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9924   -1.4442   -1.8023 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -0.3405   -0.3094 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6476   -0.3026   -1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3830   -1.4687   -1.1729 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6783   -0.3551    2.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1772   -0.8748    2.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1063   -2.2893    2.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1196   -3.4137    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1471   -3.0956   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2295   -1.6975   -1.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0311    0.9814   -2.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6994    3.3036   -2.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2617    4.7715   -0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422    3.8786    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4688    1.5356    1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3494   -0.0500   -2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2786    0.5668   -0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9549   -1.6111   -0.4030 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19  2  1  0
 10  5  1  0
 16 11  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 20 33  1  0
 20 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(Hydroxymethyl)-5,5-diphenylhydantoin	HMDB

Chemical Formula

C₁₆H₁₄N₂O₃

Average Molecular Weight

282.299

Monoisotopic Molecular Weight

282.100442319

IUPAC Name

3-(hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione

Traditional Name

phenytoin,3-hydroxymethyl

CAS Registry Number

Not Available

SMILES

OCN1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H14N2O3/c19-11-18-14(20)16(17-15(18)21,12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,19H,11H2,(H,17,21)

InChI Key

QQBKLRXLVRDKEB-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
Dicarboximide
Carbonic acid derivative
Urea
Alkanolamine
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organooxygen 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)

Source

Exogenous

Exogenous (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	1.67	ALOGPS
logP	1.79	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	10.55	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.64 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	76.18 m³·mol⁻¹	ChemAxon
Polarizability	28.57 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
DeepCCS	[M+H]+	160.296	30932474
DeepCCS	[M-H]-	157.938	30932474
DeepCCS	[M-2H]-	190.955	30932474
DeepCCS	[M+Na]+	166.389	30932474
AllCCS	[M+H]+	165.3	32859911
AllCCS	[M+H-H2O]+	161.9	32859911
AllCCS	[M+NH4]+	168.5	32859911
AllCCS	[M+Na]+	169.4	32859911
AllCCS	[M-H]-	163.7	32859911
AllCCS	[M+Na-2H]-	163.1	32859911
AllCCS	[M+HCOO]-	162.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione	OCN1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1	3456.1	Standard polar	33892256
3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione	OCN1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1	2529.7	Standard non polar	33892256
3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione	OCN1C(=O)NC(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1	2436.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione,2TMS,isomer #1	C[Si](C)(C)OCN1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2422.8	Semi standard non polar	33892256
3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione,2TMS,isomer #1	C[Si](C)(C)OCN1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2491.8	Standard non polar	33892256
3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione,2TMS,isomer #1	C[Si](C)(C)OCN1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	3147.4	Standard polar	33892256
3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCN1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2880.0	Semi standard non polar	33892256
3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCN1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	2897.2	Standard non polar	33892256
3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCN1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O	3244.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fsi-1960000000-d57b6e9c7e4d1a34ed8a	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione 10V, Positive-QTOF	splash10-001i-0090000000-c2ec2f4d58b809f77ef7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione 20V, Positive-QTOF	splash10-0ue9-0190000000-cdaf8e510cb1739065aa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione 40V, Positive-QTOF	splash10-0ldi-1920000000-0ede124782d580b29e0b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione 10V, Negative-QTOF	splash10-001i-0090000000-6129372a73f3c25aee63	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione 20V, Negative-QTOF	splash10-0a4l-3290000000-768ca0e8b6a2d225eadc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione 40V, Negative-QTOF	splash10-0kml-3920000000-e5db686b6a057d3faeff	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

141746

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

161366

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 3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione (HMDB0245789)

MOL for HMDB0245789 (3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione)

3D MOL for HMDB0245789 (3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione)

3D SDF for HMDB0245789 (3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione)

3D-SDF for HMDB0245789 (3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione)

PDB for HMDB0245789 (3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione)

3D PDB for HMDB0245789 (3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione)

SMILES for HMDB0245789 (3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione)

INCHI for HMDB0245789 (3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione)

Structure for HMDB0245789 (3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione)

3D Structure for HMDB0245789 (3-(Hydroxymethyl)-5,5-diphenylimidazolidine-2,4-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra