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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:38 UTC

Update Date

2021-09-14 15:00:47 UTC

HMDB ID

HMDB0013969

Secondary Accession Numbers

HMDB13969

Metabolite Identification

Common Name

Zileuton sulfoxide

Description

Zileuton sulfoxide belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system. Zileuton sulfoxide is a metabolite of Zileuton. Zileuton sulfoxide is an extremely weak basic (essentially neutral) compound (based on its pKa). These are organic compounds containing a benzene fused to a thiepine ring (a five-member ring with six carbon atoms and one sulfur atom). Zileuton sulfoxide is only found in individuals that have used or taken Zileuton.

Structure

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

HMDB0013969
     RDKit          3D
Zileuton sulfoxide
 29 30  0  0  0  0  0  0  0  0999 V2000
    0.1000    1.6885    2.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851    0.3630    1.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114   -0.1843    0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1650    0.2798    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7248   -0.4798   -1.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8443   -0.1867   -1.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2382   -1.0394   -2.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5721   -2.2093   -3.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4633   -2.4703   -2.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0657   -1.6340   -1.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2791   -1.7104   -0.1839 S   0  0  0  0  0  4  0  0  0  0  0  0
    0.1372   -2.8222    0.8149 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0514    0.6193    1.3997 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0144   -0.0144    2.1485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4678    1.4532    0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8379    1.6420    0.0846 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6246    2.0477   -0.3438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8139    1.4359    2.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491    2.1856    2.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1145    2.3072    1.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6498   -0.3208    2.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5894    1.2417    0.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4351    0.7358   -1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1144   -0.8067   -3.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8845   -2.8775   -3.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9505   -3.4003   -2.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6720    0.6675    2.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667    0.8957   -0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520    2.5930    0.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 11  3  1  0
 10  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 14 27  1  0
 16 28  1  0
 16 29  1  0
M  END


  Mrv0541 06191310352D          

 17 18  0  0  0  0            999 V2000
    8.3443   -3.1682    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.6508   -5.2611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3008   -3.8322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0633   -4.5466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3008   -5.2611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6508   -3.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8258   -3.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5637   -4.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3443   -4.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5637   -3.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0633   -3.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8491   -4.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8491   -3.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1346   -4.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1346   -3.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8883   -4.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6006   -2.3840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  0  0  0  0
  2  4  1  0  0  0  0
  3 16  2  0  0  0  0
  4  6  1  0  0  0  0
  4 16  1  0  0  0  0
  5 16  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  9  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  2  0  0  0  0
 10 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  2  0  0  0  0
  1 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013969

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(N(O)C(N)=O)C1=CC2=CC=CC=C2S1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O3S/c1-7(13(15)11(12)14)10-6-8-4-2-3-5-9(8)17(10)16/h2-7,15H,1H3,(H2,12,14)

> <INCHI_KEY>
KWEAXQJUQDQMNY-UHFFFAOYSA-N

> <FORMULA>
C11H12N2O3S

> <MOLECULAR_WEIGHT>
252.29

> <EXACT_MASS>
252.05686295

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.75182620058347

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-1-[1-(1-oxo-1λ⁴-benzothiophen-2-yl)ethyl]urea

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
0.11503763866666655

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.92378470756903

> <JCHEM_PKA_STRONGEST_BASIC>
-5.456536002196473

> <JCHEM_POLAR_SURFACE_AREA>
83.63

> <JCHEM_REFRACTIVITY>
67.06310000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-1-[1-(1-oxo-1λ⁴-benzothiophen-2-yl)ethyl]urea

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013969
     RDKit          3D
Zileuton sulfoxide
 29 30  0  0  0  0  0  0  0  0999 V2000
    0.1000    1.6885    2.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851    0.3630    1.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114   -0.1843    0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1650    0.2798    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7248   -0.4798   -1.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8443   -0.1867   -1.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2382   -1.0394   -2.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5721   -2.2093   -3.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4633   -2.4703   -2.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0657   -1.6340   -1.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2791   -1.7104   -0.1839 S   0  0  0  0  0  4  0  0  0  0  0  0
    0.1372   -2.8222    0.8149 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0514    0.6193    1.3997 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0144   -0.0144    2.1485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4678    1.4532    0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8379    1.6420    0.0846 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6246    2.0477   -0.3438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8139    1.4359    2.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491    2.1856    2.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1145    2.3072    1.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6498   -0.3208    2.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5894    1.2417    0.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4351    0.7358   -1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1144   -0.8067   -3.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8845   -2.8775   -3.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9505   -3.4003   -2.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6720    0.6675    2.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667    0.8957   -0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520    2.5930    0.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 11  3  1  0
 10  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 14 27  1  0
 16 28  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1  S   UNK     0      15.576  -5.914   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      18.015  -9.821   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      21.095  -7.153   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      18.785  -8.487   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      21.095  -9.821   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      18.015  -7.153   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.475  -7.153   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.119  -7.923   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.576  -8.393   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.119  -6.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.785  -5.820   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.785  -8.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.785  -5.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.451  -7.923   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.451  -6.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.325  -8.487   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.054  -4.450   0.000  0.00  0.00           O+0
CONECT    1    7   10   17                                                  
CONECT    2    4                                                            
CONECT    3   16                                                            
CONECT    4    2    6   16                                                  
CONECT    5   16                                                            
CONECT    6    4    7   11                                                  
CONECT    7    1    6    9                                                  
CONECT    8    9   10   12                                                  
CONECT    9    7    8                                                       
CONECT   10    1    8   13                                                  
CONECT   11    6                                                            
CONECT   12    8   14                                                       
CONECT   13   10   15                                                       
CONECT   14   12   15                                                       
CONECT   15   13   14                                                       
CONECT   16    3    4    5                                                  
CONECT   17    1                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0013969
HETATM    1  C1  UNL     1       0.100   1.689   2.243  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.685   0.363   1.759  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.111  -0.184   0.628  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.165   0.280   0.037  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.725  -0.480  -1.043  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.844  -0.187  -1.824  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.238  -1.039  -2.826  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.572  -2.209  -3.119  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.463  -2.470  -2.324  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.066  -1.634  -1.331  1.00  0.00           C  
HETATM   11  S1  UNL     1       0.279  -1.710  -0.184  1.00  0.00           S  
HETATM   12  O1  UNL     1       0.137  -2.822   0.815  1.00  0.00           O  
HETATM   13  N1  UNL     1       2.051   0.619   1.400  1.00  0.00           N  
HETATM   14  O2  UNL     1       3.014  -0.014   2.148  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.468   1.453   0.361  1.00  0.00           C  
HETATM   16  N2  UNL     1       3.838   1.642   0.085  1.00  0.00           N  
HETATM   17  O3  UNL     1       1.625   2.048  -0.344  1.00  0.00           O  
HETATM   18  H1  UNL     1      -0.814   1.436   2.805  1.00  0.00           H  
HETATM   19  H2  UNL     1       0.849   2.186   2.890  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.114   2.307   1.340  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.650  -0.321   2.601  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.589   1.242   0.389  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.435   0.736  -1.651  1.00  0.00           H  
HETATM   24  H7  UNL     1      -4.114  -0.807  -3.434  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.884  -2.877  -3.908  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.951  -3.400  -2.573  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.672   0.668   2.449  1.00  0.00           H  
HETATM   28  H11 UNL     1       4.467   0.896  -0.285  1.00  0.00           H  
HETATM   29  H12 UNL     1       4.252   2.593   0.262  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   13   21
CONECT    3    4    4   11
CONECT    4    5   22
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   11
CONECT   11   12   12
CONECT   13   14   15
CONECT   14   27
CONECT   15   16   17   17
CONECT   16   28   29
END

HMDB0013969
     RDKit          3D
Zileuton sulfoxide
 29 30  0  0  0  0  0  0  0  0999 V2000
    0.1000    1.6885    2.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851    0.3630    1.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114   -0.1843    0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1650    0.2798    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7248   -0.4798   -1.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8443   -0.1867   -1.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2382   -1.0394   -2.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5721   -2.2093   -3.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4633   -2.4703   -2.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0657   -1.6340   -1.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2791   -1.7104   -0.1839 S   0  0  0  0  0  4  0  0  0  0  0  0
    0.1372   -2.8222    0.8149 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0514    0.6193    1.3997 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0144   -0.0144    2.1485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4678    1.4532    0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8379    1.6420    0.0846 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6246    2.0477   -0.3438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8139    1.4359    2.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491    2.1856    2.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1145    2.3072    1.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6498   -0.3208    2.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5894    1.2417    0.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4351    0.7358   -1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1144   -0.8067   -3.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8845   -2.8775   -3.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9505   -3.4003   -2.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6720    0.6675    2.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667    0.8957   -0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520    2.5930    0.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 11  3  1  0
 10  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 14 27  1  0
 16 28  1  0
 16 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Zileuton sulphoxide	Generator

Chemical Formula

C₁₁H₁₂N₂O₃S

Average Molecular Weight

252.29

Monoisotopic Molecular Weight

252.05686295

IUPAC Name

1-hydroxy-1-[1-(1-oxo-1λ⁴-benzothiophen-2-yl)ethyl]urea

Traditional Name

1-hydroxy-1-[1-(1-oxo-1λ⁴-benzothiophen-2-yl)ethyl]urea

CAS Registry Number

Not Available

SMILES

CC(N(O)C(N)=O)C1=CC2=CC=CC=C2S1=O

InChI Identifier

InChI=1S/C11H12N2O3S/c1-7(13(15)11(12)14)10-6-8-4-2-3-5-9(8)17(10)16/h2-7,15H,1H3,(H2,12,14)

InChI Key

KWEAXQJUQDQMNY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiophenes

Sub Class

1-benzothiophenes

Direct Parent

1-benzothiophenes

Alternative Parents

Substituents

1-benzothiophene
2,3,5-trisubstituted thiophene
Thiophene sulfoxide
Benzenoid
Thiophene
Heteroaromatic compound
Carbonic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Liver (HMDB: HMDB0013969)
Kidney (HMDB: HMDB0013969)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013969)

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
Water Solubility	6.22 g/L	ALOGPS
logP	0.4	ALOGPS
logP	0.12	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	8.92	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.63 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.06 m³·mol⁻¹	ChemAxon
Polarizability	24.75 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
DarkChem	[M+H]+	155.068	31661259
DarkChem	[M-H]-	149.596	31661259
DeepCCS	[M+H]+	147.828	30932474
DeepCCS	[M-H]-	145.47	30932474
DeepCCS	[M-2H]-	179.394	30932474
DeepCCS	[M+Na]+	154.339	30932474
AllCCS	[M+H]+	154.7	32859911
AllCCS	[M+H-H2O]+	150.9	32859911
AllCCS	[M+NH4]+	158.3	32859911
AllCCS	[M+Na]+	159.3	32859911
AllCCS	[M-H]-	154.9	32859911
AllCCS	[M+Na-2H]-	155.0	32859911
AllCCS	[M+HCOO]-	155.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zileuton sulfoxide	CC(N(O)C(N)=O)C1=CC2=CC=CC=C2S1=O	3625.6	Standard polar	33892256
Zileuton sulfoxide	CC(N(O)C(N)=O)C1=CC2=CC=CC=C2S1=O	2138.5	Standard non polar	33892256
Zileuton sulfoxide	CC(N(O)C(N)=O)C1=CC2=CC=CC=C2S1=O	2435.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zileuton sulfoxide,1TMS,isomer #1	CC(C1=CC2=CC=CC=C2S1=O)N(O)C(=O)N[Si](C)(C)C	2368.6	Semi standard non polar	33892256
Zileuton sulfoxide,1TMS,isomer #1	CC(C1=CC2=CC=CC=C2S1=O)N(O)C(=O)N[Si](C)(C)C	2504.1	Standard non polar	33892256
Zileuton sulfoxide,1TMS,isomer #1	CC(C1=CC2=CC=CC=C2S1=O)N(O)C(=O)N[Si](C)(C)C	3421.2	Standard polar	33892256
Zileuton sulfoxide,2TMS,isomer #1	CC(C1=CC2=CC=CC=C2S1=O)N(O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2424.7	Semi standard non polar	33892256
Zileuton sulfoxide,2TMS,isomer #1	CC(C1=CC2=CC=CC=C2S1=O)N(O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2646.5	Standard non polar	33892256
Zileuton sulfoxide,2TMS,isomer #1	CC(C1=CC2=CC=CC=C2S1=O)N(O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	3207.5	Standard polar	33892256
Zileuton sulfoxide,1TBDMS,isomer #1	CC(C1=CC2=CC=CC=C2S1=O)N(O)C(=O)N[Si](C)(C)C(C)(C)C	2615.0	Semi standard non polar	33892256
Zileuton sulfoxide,1TBDMS,isomer #1	CC(C1=CC2=CC=CC=C2S1=O)N(O)C(=O)N[Si](C)(C)C(C)(C)C	2728.7	Standard non polar	33892256
Zileuton sulfoxide,1TBDMS,isomer #1	CC(C1=CC2=CC=CC=C2S1=O)N(O)C(=O)N[Si](C)(C)C(C)(C)C	3476.8	Standard polar	33892256
Zileuton sulfoxide,2TBDMS,isomer #1	CC(C1=CC2=CC=CC=C2S1=O)N(O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2858.7	Semi standard non polar	33892256
Zileuton sulfoxide,2TBDMS,isomer #1	CC(C1=CC2=CC=CC=C2S1=O)N(O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3048.3	Standard non polar	33892256
Zileuton sulfoxide,2TBDMS,isomer #1	CC(C1=CC2=CC=CC=C2S1=O)N(O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3265.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Zileuton sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9510000000-164f02acfadc833ab2c8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zileuton sulfoxide 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 - Zileuton sulfoxide 10V, Positive-QTOF	splash10-0w29-0190000000-9fcfd6144b50b0ff9b8c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton sulfoxide 20V, Positive-QTOF	splash10-0imi-5690000000-aca4734f1a35c664b9d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton sulfoxide 40V, Positive-QTOF	splash10-004i-3900000000-316cf385442a47312144	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton sulfoxide 10V, Negative-QTOF	splash10-0k96-6290000000-263bf1e93428dcfc247a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton sulfoxide 20V, Negative-QTOF	splash10-052f-9370000000-52e19beea929ff214c24	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton sulfoxide 40V, Negative-QTOF	splash10-0006-9300000000-a73cb862f1f67ceca69d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton sulfoxide 10V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton sulfoxide 20V, Negative-QTOF	splash10-0006-9500000000-cdafd3ed2839848f208f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton sulfoxide 40V, Negative-QTOF	splash10-0f6t-0900000000-5ffcb82d14c3e859fa77	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton sulfoxide 10V, Positive-QTOF	splash10-01t9-0970000000-0413f23bf76974dd8898	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton sulfoxide 20V, Positive-QTOF	splash10-004i-0910000000-7bef9450cea70f770ad5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton sulfoxide 40V, Positive-QTOF	splash10-004l-4900000000-e79cc4e7f97177fc708b	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	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

71752998

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 Zileuton sulfoxide (HMDB0013969)

MOL for HMDB0013969 (Zileuton sulfoxide)

3D MOL for HMDB0013969 (Zileuton sulfoxide)

3D SDF for HMDB0013969 (Zileuton sulfoxide)

3D-SDF for HMDB0013969 (Zileuton sulfoxide)

PDB for HMDB0013969 (Zileuton sulfoxide)

3D PDB for HMDB0013969 (Zileuton sulfoxide)

SMILES for HMDB0013969 (Zileuton sulfoxide)

INCHI for HMDB0013969 (Zileuton sulfoxide)

Structure for HMDB0013969 (Zileuton sulfoxide)

3D Structure for HMDB0013969 (Zileuton sulfoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra