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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

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

HMDB0013968

Secondary Accession Numbers

HMDB13968

Metabolite Identification

Common Name

Hydroxyzileuton

Description

Hydroxyzileuton is only found in individuals that have used or taken Zileuton. Hydroxyzileuton is a metabolite of Zileuton. Hydroxyzileuton belongs to the family of Benzothiophenes. These are organic compounds containing a benzene fused to a thiepine ring (a five-member ring with six carbon atoms and one sulfur atom).

Structure

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

HMDB0013968
     RDKit          3D
Hydroxyzileuton
 29 30  0  0  0  0  0  0  0  0999 V2000
    2.2446   -0.9247    2.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0056   -0.4198    0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5183   -0.2179    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906   -0.9841   -0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6853   -0.5872   -0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7732   -1.2226   -0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0233   -0.7197   -0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3471    0.4160    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6333    0.8955    0.1908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2693    1.0408    0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753    0.5322    0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4563    1.0173    1.1765 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6446    0.8421    0.4363 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3634    1.8540    1.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5623    1.0647   -0.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8421   -0.0099   -1.5002 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1153    2.1733   -0.7778 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6403   -1.8424    2.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8310   -0.1795    2.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -1.0461    2.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2813   -1.1860   -0.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043   -1.8857   -0.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6508   -2.1210   -1.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8610   -1.2312   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9726    1.5588   -0.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4550    1.9326    1.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976    2.0628    1.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7227   -0.5377   -1.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2122   -0.2747   -2.2791 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
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 12  3  1  0
 11  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
  9 25  1  0
 10 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
    8.7015   -2.8567    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.0080   -4.9495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6580   -3.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4204   -4.2351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6580   -4.9495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0080   -3.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1830   -3.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9209   -3.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7015   -4.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9209   -3.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4204   -2.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2063   -4.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2063   -2.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4918   -3.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4918   -3.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2455   -4.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7773   -2.6956    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
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013968

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
ZQQVPNNYZLDMMO-UHFFFAOYSA-N

> <FORMULA>
C11H12N2O3S

> <MOLECULAR_WEIGHT>
252.29

> <EXACT_MASS>
252.05686295

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.184521361907805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-1-[1-(6-hydroxy-1-benzothiophen-2-yl)ethyl]urea

> <ALOGPS_LOGP>
1.76

> <JCHEM_LOGP>
1.7026075133333332

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.509947383595595

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.733797170852904

> <JCHEM_PKA_STRONGEST_BASIC>
-5.494153654142637

> <JCHEM_POLAR_SURFACE_AREA>
86.79

> <JCHEM_REFRACTIVITY>
63.94040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-1-[1-(6-hydroxy-1-benzothiophen-2-yl)ethyl]urea

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013968
     RDKit          3D
Hydroxyzileuton
 29 30  0  0  0  0  0  0  0  0999 V2000
    2.2446   -0.9247    2.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0056   -0.4198    0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5183   -0.2179    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906   -0.9841   -0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6853   -0.5872   -0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7732   -1.2226   -0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0233   -0.7197   -0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3471    0.4160    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6333    0.8955    0.1908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2693    1.0408    0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753    0.5322    0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4563    1.0173    1.1765 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6446    0.8421    0.4363 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3634    1.8540    1.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5623    1.0647   -0.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8421   -0.0099   -1.5002 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1153    2.1733   -0.7778 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6403   -1.8424    2.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8310   -0.1795    2.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -1.0461    2.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2813   -1.1860   -0.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043   -1.8857   -0.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6508   -2.1210   -1.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8610   -1.2312   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9726    1.5588   -0.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4550    1.9326    1.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976    2.0628    1.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7227   -0.5377   -1.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2122   -0.2747   -2.2791 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
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 12  3  1  0
 11  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
  9 25  1  0
 10 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      16.243  -5.332   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      18.682  -9.239   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      21.762  -6.572   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      19.451  -7.905   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      21.762  -9.239   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      18.682  -6.572   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.142  -6.572   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.786  -7.342   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.243  -7.811   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.786  -5.802   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.451  -5.238   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.452  -8.112   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.452  -5.032   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.118  -7.342   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.118  -5.802   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.992  -7.905   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.784  -5.032   0.000  0.00  0.00           O+0
CONECT    1    7   10                                                       
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   17                                                  
CONECT   16    3    4    5                                                  
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0013968
HETATM    1  C1  UNL     1       2.245  -0.925   2.044  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.006  -0.420   0.629  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.518  -0.218   0.508  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.391  -0.984  -0.171  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.685  -0.587  -0.127  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.773  -1.223  -0.748  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.023  -0.720  -0.625  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.347   0.416   0.090  1.00  0.00           C  
HETATM    9  O1  UNL     1      -5.633   0.895   0.191  1.00  0.00           O  
HETATM   10  C9  UNL     1      -3.269   1.041   0.702  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.975   0.532   0.582  1.00  0.00           C  
HETATM   12  S1  UNL     1      -0.456   1.017   1.176  1.00  0.00           S  
HETATM   13  N1  UNL     1       2.645   0.842   0.436  1.00  0.00           N  
HETATM   14  O2  UNL     1       2.363   1.854   1.289  1.00  0.00           O  
HETATM   15  C11 UNL     1       3.562   1.065  -0.619  1.00  0.00           C  
HETATM   16  N2  UNL     1       3.842  -0.010  -1.500  1.00  0.00           N  
HETATM   17  O3  UNL     1       4.115   2.173  -0.778  1.00  0.00           O  
HETATM   18  H1  UNL     1       1.640  -1.842   2.185  1.00  0.00           H  
HETATM   19  H2  UNL     1       1.831  -0.179   2.768  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.307  -1.046   2.263  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.281  -1.186  -0.096  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.004  -1.886  -0.713  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.651  -2.121  -1.337  1.00  0.00           H  
HETATM   24  H7  UNL     1      -4.861  -1.231  -1.118  1.00  0.00           H  
HETATM   25  H8  UNL     1      -5.973   1.559  -0.494  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.455   1.933   1.275  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.198   2.063   1.777  1.00  0.00           H  
HETATM   28  H11 UNL     1       4.723  -0.538  -1.336  1.00  0.00           H  
HETATM   29  H12 UNL     1       3.212  -0.275  -2.279  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   13   21
CONECT    3    4    4   12
CONECT    4    5   22
CONECT    5    6    6   11
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9   10
CONECT    9   25
CONECT   10   11   11   26
CONECT   11   12
CONECT   13   14   15
CONECT   14   27
CONECT   15   16   17   17
CONECT   16   28   29
END

HMDB0013968
     RDKit          3D
Hydroxyzileuton
 29 30  0  0  0  0  0  0  0  0999 V2000
    2.2446   -0.9247    2.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0056   -0.4198    0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5183   -0.2179    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906   -0.9841   -0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6853   -0.5872   -0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7732   -1.2226   -0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0233   -0.7197   -0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3471    0.4160    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6333    0.8955    0.1908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2693    1.0408    0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753    0.5322    0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4563    1.0173    1.1765 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6446    0.8421    0.4363 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3634    1.8540    1.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5623    1.0647   -0.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8421   -0.0099   -1.5002 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1153    2.1733   -0.7778 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6403   -1.8424    2.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8310   -0.1795    2.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -1.0461    2.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2813   -1.1860   -0.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043   -1.8857   -0.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6508   -2.1210   -1.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8610   -1.2312   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9726    1.5588   -0.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4550    1.9326    1.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976    2.0628    1.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7227   -0.5377   -1.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2122   -0.2747   -2.2791 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
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 12  3  1  0
 11  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
  9 25  1  0
 10 26  1  0
 14 27  1  0
 16 28  1  0
 16 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂N₂O₃S

Average Molecular Weight

252.29

Monoisotopic Molecular Weight

252.05686295

IUPAC Name

1-hydroxy-1-[1-(6-hydroxy-1-benzothiophen-2-yl)ethyl]urea

Traditional Name

1-hydroxy-1-[1-(6-hydroxy-1-benzothiophen-2-yl)ethyl]urea

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

ZQQVPNNYZLDMMO-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
1-hydroxy-2-unsubstituted benzenoid
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: HMDB0013968)
Kidney (HMDB: HMDB0013968)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013968)

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	0.084 g/L	ALOGPS
logP	1.76	ALOGPS
logP	1.7	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.73	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.79 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.94 m³·mol⁻¹	ChemAxon
Polarizability	25.18 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]+	154.962	31661259
DarkChem	[M-H]-	153.624	31661259
DeepCCS	[M+H]+	150.872	30932474
DeepCCS	[M-H]-	148.514	30932474
DeepCCS	[M-2H]-	181.735	30932474
DeepCCS	[M+Na]+	156.965	30932474
AllCCS	[M+H]+	155.0	32859911
AllCCS	[M+H-H2O]+	151.2	32859911
AllCCS	[M+NH4]+	158.4	32859911
AllCCS	[M+Na]+	159.4	32859911
AllCCS	[M-H]-	156.4	32859911
AllCCS	[M+Na-2H]-	156.5	32859911
AllCCS	[M+HCOO]-	156.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyzileuton	CC(N(O)C(N)=O)C1=CC2=CC=C(O)C=C2S1	3897.4	Standard polar	33892256
Hydroxyzileuton	CC(N(O)C(N)=O)C1=CC2=CC=C(O)C=C2S1	2093.9	Standard non polar	33892256
Hydroxyzileuton	CC(N(O)C(N)=O)C1=CC2=CC=C(O)C=C2S1	2627.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyzileuton,1TMS,isomer #1	CC(C1=CC2=CC=C(O[Si](C)(C)C)C=C2S1)N(O)C(N)=O	2441.2	Semi standard non polar	33892256
Hydroxyzileuton,1TMS,isomer #2	CC(C1=CC2=CC=C(O)C=C2S1)N(O)C(=O)N[Si](C)(C)C	2462.4	Semi standard non polar	33892256
Hydroxyzileuton,2TMS,isomer #1	CC(C1=CC2=CC=C(O[Si](C)(C)C)C=C2S1)N(O)C(=O)N[Si](C)(C)C	2453.8	Semi standard non polar	33892256
Hydroxyzileuton,2TMS,isomer #1	CC(C1=CC2=CC=C(O[Si](C)(C)C)C=C2S1)N(O)C(=O)N[Si](C)(C)C	2519.4	Standard non polar	33892256
Hydroxyzileuton,2TMS,isomer #1	CC(C1=CC2=CC=C(O[Si](C)(C)C)C=C2S1)N(O)C(=O)N[Si](C)(C)C	3172.3	Standard polar	33892256
Hydroxyzileuton,2TMS,isomer #2	CC(C1=CC2=CC=C(O)C=C2S1)N(O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2537.8	Semi standard non polar	33892256
Hydroxyzileuton,2TMS,isomer #2	CC(C1=CC2=CC=C(O)C=C2S1)N(O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2624.4	Standard non polar	33892256
Hydroxyzileuton,2TMS,isomer #2	CC(C1=CC2=CC=C(O)C=C2S1)N(O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	3257.2	Standard polar	33892256
Hydroxyzileuton,3TMS,isomer #1	CC(C1=CC2=CC=C(O[Si](C)(C)C)C=C2S1)N(O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2474.4	Semi standard non polar	33892256
Hydroxyzileuton,3TMS,isomer #1	CC(C1=CC2=CC=C(O[Si](C)(C)C)C=C2S1)N(O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2589.1	Standard non polar	33892256
Hydroxyzileuton,3TMS,isomer #1	CC(C1=CC2=CC=C(O[Si](C)(C)C)C=C2S1)N(O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2908.9	Standard polar	33892256
Hydroxyzileuton,1TBDMS,isomer #1	CC(C1=CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2S1)N(O)C(N)=O	2719.8	Semi standard non polar	33892256
Hydroxyzileuton,1TBDMS,isomer #2	CC(C1=CC2=CC=C(O)C=C2S1)N(O)C(=O)N[Si](C)(C)C(C)(C)C	2731.3	Semi standard non polar	33892256
Hydroxyzileuton,2TBDMS,isomer #1	CC(C1=CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2S1)N(O)C(=O)N[Si](C)(C)C(C)(C)C	2945.4	Semi standard non polar	33892256
Hydroxyzileuton,2TBDMS,isomer #1	CC(C1=CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2S1)N(O)C(=O)N[Si](C)(C)C(C)(C)C	2902.9	Standard non polar	33892256
Hydroxyzileuton,2TBDMS,isomer #1	CC(C1=CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2S1)N(O)C(=O)N[Si](C)(C)C(C)(C)C	3282.2	Standard polar	33892256
Hydroxyzileuton,2TBDMS,isomer #2	CC(C1=CC2=CC=C(O)C=C2S1)N(O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2969.3	Semi standard non polar	33892256
Hydroxyzileuton,2TBDMS,isomer #2	CC(C1=CC2=CC=C(O)C=C2S1)N(O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2966.9	Standard non polar	33892256
Hydroxyzileuton,2TBDMS,isomer #2	CC(C1=CC2=CC=C(O)C=C2S1)N(O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3250.5	Standard polar	33892256
Hydroxyzileuton,3TBDMS,isomer #1	CC(C1=CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2S1)N(O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3191.0	Semi standard non polar	33892256
Hydroxyzileuton,3TBDMS,isomer #1	CC(C1=CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2S1)N(O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3127.0	Standard non polar	33892256
Hydroxyzileuton,3TBDMS,isomer #1	CC(C1=CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2S1)N(O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3138.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyzileuton GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-3900000000-0bdea288f9e16d003d8c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyzileuton GC-MS (1 TMS) - 70eV, Positive	splash10-05r0-1900000000-5198e17adbd0699e04b9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyzileuton 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 - Hydroxyzileuton 10V, Positive-QTOF	splash10-0w29-0190000000-8e78cea746aff6d0e560	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyzileuton 20V, Positive-QTOF	splash10-0ik9-2490000000-54ad52e711135e2b735b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyzileuton 40V, Positive-QTOF	splash10-004i-2900000000-bb9be06d9b6741ae5d31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyzileuton 10V, Negative-QTOF	splash10-0k96-7290000000-16fd8ffd8d7795dbe551	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyzileuton 20V, Negative-QTOF	splash10-052f-9480000000-84fe315ad03945067ad8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyzileuton 40V, Negative-QTOF	splash10-0006-9500000000-0dfedd364e419f7a0dad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyzileuton 10V, Negative-QTOF	splash10-0006-9200000000-c711bc896a0675b56a41	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyzileuton 20V, Negative-QTOF	splash10-0007-3900000000-32b7f66d095b512c6775	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyzileuton 40V, Negative-QTOF	splash10-0002-2900000000-451158baa83584ee77ab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyzileuton 10V, Positive-QTOF	splash10-004i-0900000000-f71b86df29926e80d9fe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyzileuton 20V, Positive-QTOF	splash10-004i-0910000000-60edf4cb5f08a28ab796	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyzileuton 40V, Positive-QTOF	splash10-06vl-1900000000-ac99ae34207e651728eb	2021-09-23	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

35032780

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750722

PDB ID

Not Available

ChEBI ID

145222

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

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

2. Arachidonate 5-lipoxygenase

General function:: Involved in metal ion binding
Specific function:: Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:: ALOX5
Uniprot ID:: P09917
Molecular weight:: 77982.595

References

Wenzel SE: Leukotriene receptor antagonists and related compounds. Can Respir J. 1999 Mar-Apr;6(2):189-93. [PubMed:10322101 ]
Hardy DB, Pereria LE, Yang K: Prostaglandins and leukotriene B4 are potent inhibitors of 11beta-hydroxysteroid dehydrogenase type 2 activity in human choriocarcinoma JEG-3 cells. Biol Reprod. 1999 Jul;61(1):40-5. [PubMed:10377029 ]
Yamashita M, Kushihara M, Hirasawa N, Takasaki W, Takahagi H, Takayanagi M, Ohuchi K: Inhibition by troglitazone of the antigen-induced production of leukotrienes in immunoglobulin E-sensitized RBL-2H3 cells. Br J Pharmacol. 2000 Jan;129(2):367-73. [PubMed:10694244 ]
Qian C, Hwang SB, Libertine-Garahan L, Eckman JB, Cai X, Scannell RT, Yeh CG: Anti-inflammatory activities of LDP-392, a dual PAF receptor antagonist and 5-lipoxygenase inhibitor. Pharmacol Res. 2001 Sep;44(3):213-20. [PubMed:11529688 ]
Coffey MJ, Phare SM, Peters-Golden M: Peroxynitrite-induced nitrotyrosination of proteins is blocked by direct 5-lipoxygenase inhibitor zileuton. J Pharmacol Exp Ther. 2001 Oct;299(1):198-203. [PubMed:11561080 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Zouboulis CC: Zileuton, a new efficient and safe systemic anti-acne drug. Dermatoendocrinol. 2009 May;1(3):188-92. [PubMed:20436887 ]
Zouboulis CC, Seltmann H, Alestas T: Zileuton prevents the activation of the leukotriene pathway and reduces sebaceous lipogenesis. Exp Dermatol. 2010 Feb;19(2):148-50. doi: 10.1111/j.1600-0625.2009.00929.x. Epub 2009 Jul 23. [PubMed:19645854 ]
Berger W, De Chandt MT, Cairns CB: Zileuton: clinical implications of 5-Lipoxygenase inhibition in severe airway disease. Int J Clin Pract. 2007 Apr;61(4):663-76. [PubMed:17394438 ]
Guidot DM, Repine MJ, Westcott JY, Repine JE: Intrinsic 5-lipoxygenase activity is required for neutrophil responsivity. Proc Natl Acad Sci U S A. 1994 Aug 16;91(17):8156-9. [PubMed:8058773 ]
Wenzel SE, Kamada AK: Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma. Ann Pharmacother. 1996 Jul-Aug;30(7-8):858-64. [PubMed:8826571 ]

Enzyme Details

3. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

4. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Machinist JM, Mayer MD, Shet MS, Ferrero JL, Rodrigues AD: Identification of the human liver cytochrome P450 enzymes involved in the metabolism of zileuton (ABT-077) and its N-dehydroxylated metabolite, Abbott-66193. Drug Metab Dispos. 1995 Oct;23(10):1163-74. [PubMed:8654206 ]

Enzyme Details

5. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

6. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Machinist JM, Mayer MD, Shet MS, Ferrero JL, Rodrigues AD: Identification of the human liver cytochrome P450 enzymes involved in the metabolism of zileuton (ABT-077) and its N-dehydroxylated metabolite, Abbott-66193. Drug Metab Dispos. 1995 Oct;23(10):1163-74. [PubMed:8654206 ]

Showing metabocard for Hydroxyzileuton (HMDB0013968)

MOL for HMDB0013968 (Hydroxyzileuton)

3D MOL for HMDB0013968 (Hydroxyzileuton)

3D SDF for HMDB0013968 (Hydroxyzileuton)

3D-SDF for HMDB0013968 (Hydroxyzileuton)

PDB for HMDB0013968 (Hydroxyzileuton)

3D PDB for HMDB0013968 (Hydroxyzileuton)

SMILES for HMDB0013968 (Hydroxyzileuton)

INCHI for HMDB0013968 (Hydroxyzileuton)

Structure for HMDB0013968 (Hydroxyzileuton)

3D Structure for HMDB0013968 (Hydroxyzileuton)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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