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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:11:58 UTC

Update Date

2021-09-26 22:58:05 UTC

HMDB ID

HMDB0248029

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Adrafinil

Description

N-hydroxy2-diphenylmethanesulfinylethanimidic acid, also known as olmifon, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Based on a literature review very few articles have been published on N-hydroxy2-diphenylmethanesulfinylethanimidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Adrafinil is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Adrafinil 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

HMDB0248029
     RDKit          3D
Adrafinil
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.3121   -3.0533    0.8332 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8455   -1.7448    0.2668 S   0  0  0  0  0  4  0  0  0  0  0  0
    2.0449   -2.0995   -0.9828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7027   -0.9038   -1.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399   -0.0842   -2.3935 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909   -0.6133   -1.1484 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5356   -1.4381   -0.2668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983   -0.7150   -0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1755    0.6617   -0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584    1.4330    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716    2.7224   -0.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622    3.3050   -1.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4650    2.5555   -2.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728    1.2668   -1.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5388   -0.6316    0.8997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162   -0.5306    2.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410   -0.4496    3.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3700   -0.4715    2.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8351   -0.5725    1.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895   -0.6517    0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184   -2.6956   -1.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8606   -2.7528   -0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3780    0.0743   -3.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301   -1.1130    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0352   -1.2261   -1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2202    0.9493    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7984    3.3016    0.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108    4.3307   -1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9443    3.0327   -2.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4994    0.7258   -2.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637   -0.5143    2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6328   -0.3727    4.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0792   -0.4075    3.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8887   -0.5873    1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2350   -0.7304   -0.3904 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
  4  6  2  3
  6  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  9  1  0
 20 15  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END


  Mrv1572004221605232D          

 20 21  0  0  0  0            999 V2000
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17 14  1  0  0  0  0
 16 18  1  4  0  0  0
 20 11  1  0  0  0  0
 20 15  1  0  0  0  0
 20 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248029

> <DATABASE_NAME>
hmdb

> <SMILES>
ON=C(O)CS(=O)C(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H15NO3S/c17-14(16-18)11-20(19)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15,18H,11H2,(H,16,17)

> <INCHI_KEY>
CGNMLOKEMNBUAI-UHFFFAOYSA-N

> <FORMULA>
C15H15NO3S

> <MOLECULAR_WEIGHT>
289.35

> <EXACT_MASS>
289.077264521

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.015492658670816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-hydroxy2-diphenylmethanesulfinylethanimidic acid

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.3492568400000002

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.962861333641564

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.982689687282826

> <JCHEM_PKA_STRONGEST_BASIC>
0.36140095636163283

> <JCHEM_POLAR_SURFACE_AREA>
69.89000000000001

> <JCHEM_REFRACTIVITY>
79.67490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
adrafinil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248029
     RDKit          3D
Adrafinil
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.3121   -3.0533    0.8332 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8455   -1.7448    0.2668 S   0  0  0  0  0  4  0  0  0  0  0  0
    2.0449   -2.0995   -0.9828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7027   -0.9038   -1.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399   -0.0842   -2.3935 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909   -0.6133   -1.1484 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5356   -1.4381   -0.2668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983   -0.7150   -0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1755    0.6617   -0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584    1.4330    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716    2.7224   -0.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622    3.3050   -1.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4650    2.5555   -2.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728    1.2668   -1.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5388   -0.6316    0.8997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162   -0.5306    2.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410   -0.4496    3.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3700   -0.4715    2.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8351   -0.5725    1.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895   -0.6517    0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184   -2.6956   -1.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8606   -2.7528   -0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3780    0.0743   -3.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301   -1.1130    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0352   -1.2261   -1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2202    0.9493    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7984    3.3016    0.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108    4.3307   -1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9443    3.0327   -2.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4994    0.7258   -2.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637   -0.5143    2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6328   -0.3727    4.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0792   -0.4075    3.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8887   -0.5873    1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2350   -0.7304   -0.3904 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
  4  6  2  3
  6  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  9  1  0
 20 15  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.668   3.850   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0       2.667   4.620   0.000  0.00  0.00           S+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   12                                                       
CONECT    8    4   12                                                       
CONECT    9    5   13                                                       
CONECT   10    6   13                                                       
CONECT   11   14   20                                                       
CONECT   12    7    8   15                                                  
CONECT   13    9   10   15                                                  
CONECT   14   11   16   17                                                  
CONECT   15   12   13   20                                                  
CONECT   16   14   18                                                       
CONECT   17   14                                                            
CONECT   18   16                                                            
CONECT   19   20                                                            
CONECT   20   11   15   19                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0248029
HETATM    1  O1  UNL     1       0.312  -3.053   0.833  1.00  0.00           O  
HETATM    2  S1  UNL     1       0.845  -1.745   0.267  1.00  0.00           S  
HETATM    3  C1  UNL     1       2.045  -2.099  -0.983  1.00  0.00           C  
HETATM    4  C2  UNL     1       2.703  -0.904  -1.507  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.040  -0.084  -2.394  1.00  0.00           O  
HETATM    6  N1  UNL     1       3.891  -0.613  -1.148  1.00  0.00           N  
HETATM    7  O3  UNL     1       4.536  -1.438  -0.267  1.00  0.00           O  
HETATM    8  C3  UNL     1      -0.498  -0.715  -0.167  1.00  0.00           C  
HETATM    9  C4  UNL     1      -0.176   0.662  -0.605  1.00  0.00           C  
HETATM   10  C5  UNL     1       0.758   1.433   0.088  1.00  0.00           C  
HETATM   11  C6  UNL     1       1.072   2.722  -0.284  1.00  0.00           C  
HETATM   12  C7  UNL     1       0.462   3.305  -1.373  1.00  0.00           C  
HETATM   13  C8  UNL     1      -0.465   2.556  -2.071  1.00  0.00           C  
HETATM   14  C9  UNL     1      -0.773   1.267  -1.693  1.00  0.00           C  
HETATM   15  C10 UNL     1      -1.539  -0.632   0.900  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.116  -0.531   2.206  1.00  0.00           C  
HETATM   17  C12 UNL     1      -2.041  -0.450   3.242  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.370  -0.471   2.948  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.835  -0.572   1.641  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.890  -0.652   0.628  1.00  0.00           C  
HETATM   21  H1  UNL     1       1.618  -2.696  -1.835  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.861  -2.753  -0.531  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.378   0.074  -3.335  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.830  -1.113   0.662  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.035  -1.226  -1.033  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.220   0.949   0.939  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.798   3.302   0.268  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.711   4.331  -1.670  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.944   3.033  -2.939  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.499   0.726  -2.267  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.064  -0.514   2.426  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.633  -0.373   4.238  1.00  0.00           H  
HETATM   33  H13 UNL     1      -4.079  -0.408   3.767  1.00  0.00           H  
HETATM   34  H14 UNL     1      -4.889  -0.587   1.440  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.235  -0.730  -0.390  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    8
CONECT    3    4   21   22
CONECT    4    5    6    6
CONECT    5   23
CONECT    6    7
CONECT    7   24
CONECT    8    9   15   25
CONECT    9   10   10   14
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   30
CONECT   15   16   16   20
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   19   33
CONECT   19   20   20   34
CONECT   20   35
END

HMDB0248029
     RDKit          3D
Adrafinil
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.3121   -3.0533    0.8332 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8455   -1.7448    0.2668 S   0  0  0  0  0  4  0  0  0  0  0  0
    2.0449   -2.0995   -0.9828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7027   -0.9038   -1.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399   -0.0842   -2.3935 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909   -0.6133   -1.1484 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5356   -1.4381   -0.2668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983   -0.7150   -0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1755    0.6617   -0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584    1.4330    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716    2.7224   -0.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622    3.3050   -1.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4650    2.5555   -2.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728    1.2668   -1.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5388   -0.6316    0.8997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162   -0.5306    2.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410   -0.4496    3.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3700   -0.4715    2.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8351   -0.5725    1.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895   -0.6517    0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184   -2.6956   -1.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8606   -2.7528   -0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3780    0.0743   -3.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301   -1.1130    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0352   -1.2261   -1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2202    0.9493    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7984    3.3016    0.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108    4.3307   -1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9443    3.0327   -2.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4994    0.7258   -2.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637   -0.5143    2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6328   -0.3727    4.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0792   -0.4075    3.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8887   -0.5873    1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2350   -0.7304   -0.3904 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
  4  6  2  3
  6  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  9  1  0
 20 15  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Olmifon	Kegg
N-Hydroxy2-diphenylmethanesulfinylethanimidate	Generator
N-Hydroxy2-diphenylmethanesulphinylethanimidate	Generator
N-Hydroxy2-diphenylmethanesulphinylethanimidic acid	Generator
2-Benzhydrylsulphinyl-N-hydroxyacetamide	Generator
Lafon brand OF adrafinil	MeSH
Benzhydrylsulfinylacetohydroxamic acid	MeSH
Adrafinil	MeSH
Adrafinyl	MeSH

Chemical Formula

C₁₅H₁₅NO₃S

Average Molecular Weight

289.35

Monoisotopic Molecular Weight

289.077264521

IUPAC Name

N-hydroxy2-diphenylmethanesulfinylethanimidic acid

Traditional Name

adrafinil

CAS Registry Number

Not Available

SMILES

ON=C(O)CS(=O)C(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H15NO3S/c17-14(16-18)11-20(19)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15,18H,11H2,(H,16,17)

InChI Key

CGNMLOKEMNBUAI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Benzyl alkyl sulfoxide
Benzyl sulfoxide
Hydroxamic acid
Sulfoxide
Sulfinyl compound
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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 (HMDB: HMDB0248029)

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	2.36	ALOGPS
logP	2.35	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.98	ChemAxon
pKa (Strongest Basic)	0.36	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.67 m³·mol⁻¹	ChemAxon
Polarizability	29.02 Å³	ChemAxon
Number of Rings	2	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]+	159.835	30932474
DeepCCS	[M-H]-	157.477	30932474
DeepCCS	[M-2H]-	190.363	30932474
DeepCCS	[M+Na]+	165.928	30932474
AllCCS	[M+H]+	166.2	32859911
AllCCS	[M+H-H2O]+	162.7	32859911
AllCCS	[M+NH4]+	169.5	32859911
AllCCS	[M+Na]+	170.4	32859911
AllCCS	[M-H]-	166.2	32859911
AllCCS	[M+Na-2H]-	166.1	32859911
AllCCS	[M+HCOO]-	166.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Adrafinil	ON=C(O)CS(=O)C(C1=CC=CC=C1)C1=CC=CC=C1	3865.9	Standard polar	33892256
Adrafinil	ON=C(O)CS(=O)C(C1=CC=CC=C1)C1=CC=CC=C1	2336.3	Standard non polar	33892256
Adrafinil	ON=C(O)CS(=O)C(C1=CC=CC=C1)C1=CC=CC=C1	2500.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Adrafinil GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1920000000-9ad146ef7e15918093cf	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adrafinil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adrafinil GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adrafinil GC-MS (TBDMS_1_1) - 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 - Adrafinil 10V, Positive-QTOF	splash10-01ox-1190000000-55e02a74afcc5e853c8f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrafinil 20V, Positive-QTOF	splash10-003r-1190000000-17340024337646723d21	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrafinil 40V, Positive-QTOF	splash10-006x-9610000000-50c1ecf600caff1da392	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrafinil 10V, Negative-QTOF	splash10-052r-2190000000-b7618866ec05e41a97d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrafinil 20V, Negative-QTOF	splash10-01b9-3290000000-d25728d602280c086b36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrafinil 40V, Negative-QTOF	splash10-0v4i-8920000000-fb073f1a4b0e313ff99b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrafinil 10V, Positive-QTOF	splash10-014i-0920000000-a7db541403d34def6ee2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrafinil 20V, Positive-QTOF	splash10-014i-0900000000-c692fb05e504a5da303a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrafinil 40V, Positive-QTOF	splash10-014i-0900000000-22b429610dc6859fe5a0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrafinil 10V, Negative-QTOF	splash10-014i-0690000000-ac48a6663132c4c59202	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrafinil 20V, Negative-QTOF	splash10-01b9-9420000000-617a7f4e0692735666ff	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adrafinil 40V, Negative-QTOF	splash10-01p9-4920000000-1d51fe521303214778e8	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

2297976

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3033226

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 Adrafinil (HMDB0248029)

MOL for HMDB0248029 (Adrafinil)

3D MOL for HMDB0248029 (Adrafinil)

3D SDF for HMDB0248029 (Adrafinil)

3D-SDF for HMDB0248029 (Adrafinil)

PDB for HMDB0248029 (Adrafinil)

3D PDB for HMDB0248029 (Adrafinil)

SMILES for HMDB0248029 (Adrafinil)

INCHI for HMDB0248029 (Adrafinil)

Structure for HMDB0248029 (Adrafinil)

3D Structure for HMDB0248029 (Adrafinil)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra