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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:10:58 UTC

Update Date

2019-07-23 07:15:31 UTC

HMDB ID

HMDB0060984

Secondary Accession Numbers

HMDB60984

Metabolite Identification

Common Name

dapsone hydroxylamine

Description

dapsone hydroxylamine is a metabolite of dapsone. Dapsone (diamino-diphenyl sulfone) is a medication most commonly used in combination with rifampicin and clofazimine as multidrug therapy (MDT) for the treatment of Mycobacterium leprae infections. It is also second-line treatment for prophylaxis (prevention) against Pneumocystis pneumonia (PCP) caused by Pneumocystis jirovecii (formerly P. carinii) in HIV patients in whom CD4 counts are below 200/mm. (Wikipedia)

Structure

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

HMDB0060984
     RDKit          3D
dapsone hydroxylamine
 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.8847    1.5687    1.1861 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8042    0.7580    0.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4471    0.7747   -0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3954   -0.0264   -1.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7261   -0.8219   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3983   -1.8352   -0.5946 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.6095   -2.3050   -2.0036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2915   -2.9998    0.3516 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1192   -0.9380   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8418   -0.9732    0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0064   -0.2810    0.8015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4789    0.4563   -0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7055    1.1762   -0.1368 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4062    1.1354    1.0162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795    0.5169   -1.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -0.1959   -1.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0888   -0.8349    1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1409   -0.0342    1.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8424    1.4986    0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7386    2.2512    1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9531    1.3863   -1.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0505   -0.0719   -2.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609   -1.5584    1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687   -0.3236    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853    1.7426   -0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1736    0.5335    0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1430    1.0946   -2.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9949   -0.1943   -2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659   -1.4565    1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4272   -0.0424    2.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  2  0
  6  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
  5 17  1  0
 17 18  2  0
 18  2  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
M  END


  Mrv0541 07091309102D          

 18 19  0  0  0  0            999 V2000
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  1  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 14  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 16  2  0  0  0  0
 18 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060984

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(NO)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H12N2O3S/c13-9-1-5-11(6-2-9)18(16,17)12-7-3-10(14-15)4-8-12/h1-8,14-15H,13H2

> <INCHI_KEY>
IYDSJDWESCGRKW-UHFFFAOYSA-N

> <FORMULA>
C12H12N2O3S

> <MOLECULAR_WEIGHT>
264.3

> <EXACT_MASS>
264.05686295

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.32243328436619

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[4-(hydroxyamino)benzenesulfonyl]aniline

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
1.6074244146666663

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.91273026512178

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.033825630208714

> <JCHEM_PKA_STRONGEST_BASIC>
3.4422745404283392

> <JCHEM_POLAR_SURFACE_AREA>
92.41999999999999

> <JCHEM_REFRACTIVITY>
71.2778

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[4-(hydroxyamino)benzenesulfonyl]aniline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060984
     RDKit          3D
dapsone hydroxylamine
 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.8847    1.5687    1.1861 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8042    0.7580    0.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4471    0.7747   -0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3954   -0.0264   -1.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7261   -0.8219   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3983   -1.8352   -0.5946 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.6095   -2.3050   -2.0036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2915   -2.9998    0.3516 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1192   -0.9380   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8418   -0.9732    0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0064   -0.2810    0.8015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4789    0.4563   -0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7055    1.1762   -0.1368 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4062    1.1354    1.0162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795    0.5169   -1.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -0.1959   -1.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0888   -0.8349    1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1409   -0.0342    1.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8424    1.4986    0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7386    2.2512    1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9531    1.3863   -1.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0505   -0.0719   -2.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609   -1.5584    1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687   -0.3236    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853    1.7426   -0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1736    0.5335    0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1430    1.0946   -2.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9949   -0.1943   -2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659   -1.4565    1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4272   -0.0424    2.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  2  0
  6  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
  5 17  1  0
 17 18  2  0
 18  2  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       6.668   6.930   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       5.335   7.700   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.208   0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.128   0.770   0.000  0.00  0.00           O+0
HETATM   18  S   UNK     0       6.668   0.770   0.000  0.00  0.00           S+0
CONECT    1    5    9                                                       
CONECT    2    6    9                                                       
CONECT    3    7   10                                                       
CONECT    4    8   10                                                       
CONECT    5    1   11                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    4   12                                                       
CONECT    9    1    2   13                                                  
CONECT   10    3    4   14                                                  
CONECT   11    5    6   18                                                  
CONECT   12    7    8   18                                                  
CONECT   13    9                                                            
CONECT   14   10   15                                                       
CONECT   15   14                                                            
CONECT   16   18                                                            
CONECT   17   18                                                            
CONECT   18   11   12   16   17                                             
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0060984
HETATM    1  N1  UNL     1      -4.885   1.569   1.186  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.804   0.758   0.720  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.447   0.775  -0.601  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.395  -0.026  -1.006  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.726  -0.822  -0.092  1.00  0.00           C  
HETATM    6  S1  UNL     1      -0.398  -1.835  -0.595  1.00  0.00           S  
HETATM    7  O1  UNL     1      -0.610  -2.305  -2.004  1.00  0.00           O  
HETATM    8  O2  UNL     1      -0.291  -3.000   0.352  1.00  0.00           O  
HETATM    9  C5  UNL     1       1.119  -0.938  -0.463  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.842  -0.973   0.709  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.006  -0.281   0.801  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.479   0.456  -0.256  1.00  0.00           C  
HETATM   13  N2  UNL     1       4.705   1.176  -0.137  1.00  0.00           N  
HETATM   14  O3  UNL     1       5.406   1.135   1.016  1.00  0.00           O  
HETATM   15  C9  UNL     1       2.779   0.517  -1.454  1.00  0.00           C  
HETATM   16  C10 UNL     1       1.600  -0.196  -1.519  1.00  0.00           C  
HETATM   17  C11 UNL     1      -2.089  -0.835   1.234  1.00  0.00           C  
HETATM   18  C12 UNL     1      -3.141  -0.034   1.641  1.00  0.00           C  
HETATM   19  H1  UNL     1      -5.842   1.499   0.771  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.739   2.251   1.956  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.953   1.386  -1.334  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.051  -0.072  -2.029  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.461  -1.558   1.540  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.569  -0.324   1.750  1.00  0.00           H  
HETATM   25  H7  UNL     1       5.085   1.743  -0.924  1.00  0.00           H  
HETATM   26  H8  UNL     1       6.174   0.534   0.985  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.143   1.095  -2.293  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.995  -0.194  -2.434  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.566  -1.457   1.948  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.427  -0.042   2.679  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3    3   18
CONECT    3    4   21
CONECT    4    5    5   22
CONECT    5    6   17
CONECT    6    7    7    8    8
CONECT    6    9
CONECT    9   10   10   16
CONECT   10   11   23
CONECT   11   12   12   24
CONECT   12   13   15
CONECT   13   14   25
CONECT   14   26
CONECT   15   16   16   27
CONECT   16   28
CONECT   17   18   18   29
CONECT   18   30
END

HMDB0060984
     RDKit          3D
dapsone hydroxylamine
 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.8847    1.5687    1.1861 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8042    0.7580    0.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4471    0.7747   -0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3954   -0.0264   -1.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7261   -0.8219   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3983   -1.8352   -0.5946 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.6095   -2.3050   -2.0036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2915   -2.9998    0.3516 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1192   -0.9380   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8418   -0.9732    0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0064   -0.2810    0.8015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4789    0.4563   -0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7055    1.1762   -0.1368 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4062    1.1354    1.0162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795    0.5169   -1.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -0.1959   -1.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0888   -0.8349    1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1409   -0.0342    1.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8424    1.4986    0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7386    2.2512    1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9531    1.3863   -1.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0505   -0.0719   -2.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609   -1.5584    1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687   -0.3236    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853    1.7426   -0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1736    0.5335    0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1430    1.0946   -2.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9949   -0.1943   -2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5659   -1.4565    1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4272   -0.0424    2.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  2  0
  6  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
  5 17  1  0
 17 18  2  0
 18  2  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Amino-4'-hydroxylaminodiphenylsulfone	HMDB
4-Amino-4'-hydroxylaminodiphenylsulfone, T-labeled CPD	HMDB
4-Hydroxylamino-4'-aminophenyl sulfone	HMDB
N-Hydroxydapsone	HMDB
DDS-NOH	HMDB
HADS	HMDB

Chemical Formula

C₁₂H₁₂N₂O₃S

Average Molecular Weight

264.3

Monoisotopic Molecular Weight

264.05686295

IUPAC Name

4-[4-(hydroxyamino)benzenesulfonyl]aniline

Traditional Name

4-[4-(hydroxyamino)benzenesulfonyl]aniline

CAS Registry Number

Not Available

SMILES

NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(NO)C=C1

InChI Identifier

InChI=1S/C12H12N2O3S/c13-9-1-5-11(6-2-9)18(16,17)12-7-3-10(14-15)4-8-12/h1-8,14-15H,13H2

InChI Key

IYDSJDWESCGRKW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonyl compounds

Direct Parent

Benzenesulfonyl compounds

Alternative Parents

Substituents

Benzenesulfonyl group
N-phenylhydroxylamine
1-hydroxylamino, 2-unsubstituted benzenoid
Aniline or substituted anilines
Arylhydroxamate
Sulfone
Sulfonyl
N-organohydroxylamine
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Primary amine
Organosulfur compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

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	0.98 g/L	ALOGPS
logP	0.89	ALOGPS
logP	1.61	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	13.03	ChemAxon
pKa (Strongest Basic)	3.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.28 m³·mol⁻¹	ChemAxon
Polarizability	26.32 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]+	161.169	31661259
DarkChem	[M-H]-	161.813	31661259
DeepCCS	[M+H]+	163.471	30932474
DeepCCS	[M-H]-	161.113	30932474
DeepCCS	[M-2H]-	194.013	30932474
DeepCCS	[M+Na]+	169.564	30932474
AllCCS	[M+H]+	160.6	32859911
AllCCS	[M+H-H2O]+	157.0	32859911
AllCCS	[M+NH4]+	163.9	32859911
AllCCS	[M+Na]+	164.9	32859911
AllCCS	[M-H]-	157.2	32859911
AllCCS	[M+Na-2H]-	157.0	32859911
AllCCS	[M+HCOO]-	157.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
dapsone hydroxylamine	NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(NO)C=C1	4306.0	Standard polar	33892256
dapsone hydroxylamine	NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(NO)C=C1	3081.5	Standard non polar	33892256
dapsone hydroxylamine	NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(NO)C=C1	3045.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
dapsone hydroxylamine,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(NO)C=C2)C=C1	3155.7	Semi standard non polar	33892256
dapsone hydroxylamine,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(NO)C=C2)C=C1	2860.3	Standard non polar	33892256
dapsone hydroxylamine,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(NO)C=C2)C=C1	3716.2	Standard polar	33892256
dapsone hydroxylamine,1TMS,isomer #2	C[Si](C)(C)N(O)C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1	2981.7	Semi standard non polar	33892256
dapsone hydroxylamine,1TMS,isomer #2	C[Si](C)(C)N(O)C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1	2727.0	Standard non polar	33892256
dapsone hydroxylamine,1TMS,isomer #2	C[Si](C)(C)N(O)C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1	3875.4	Standard polar	33892256
dapsone hydroxylamine,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(NO)C=C2)C=C1)[Si](C)(C)C	3120.2	Semi standard non polar	33892256
dapsone hydroxylamine,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(NO)C=C2)C=C1)[Si](C)(C)C	2924.0	Standard non polar	33892256
dapsone hydroxylamine,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(NO)C=C2)C=C1)[Si](C)(C)C	3427.2	Standard polar	33892256
dapsone hydroxylamine,2TMS,isomer #2	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C)C=C2)C=C1	3207.3	Semi standard non polar	33892256
dapsone hydroxylamine,2TMS,isomer #2	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C)C=C2)C=C1	2871.7	Standard non polar	33892256
dapsone hydroxylamine,2TMS,isomer #2	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C)C=C2)C=C1	3359.6	Standard polar	33892256
dapsone hydroxylamine,3TMS,isomer #1	C[Si](C)(C)N(O)C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1	3115.8	Semi standard non polar	33892256
dapsone hydroxylamine,3TMS,isomer #1	C[Si](C)(C)N(O)C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1	2907.4	Standard non polar	33892256
dapsone hydroxylamine,3TMS,isomer #1	C[Si](C)(C)N(O)C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1	3170.0	Standard polar	33892256
dapsone hydroxylamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(NO)C=C2)C=C1	3430.8	Semi standard non polar	33892256
dapsone hydroxylamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(NO)C=C2)C=C1	3110.6	Standard non polar	33892256
dapsone hydroxylamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(NO)C=C2)C=C1	3686.4	Standard polar	33892256
dapsone hydroxylamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(O)C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1	3245.9	Semi standard non polar	33892256
dapsone hydroxylamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(O)C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1	2922.3	Standard non polar	33892256
dapsone hydroxylamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(O)C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1	3849.6	Standard polar	33892256
dapsone hydroxylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(NO)C=C2)C=C1)[Si](C)(C)C(C)(C)C	3656.4	Semi standard non polar	33892256
dapsone hydroxylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(NO)C=C2)C=C1)[Si](C)(C)C(C)(C)C	3367.1	Standard non polar	33892256
dapsone hydroxylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(NO)C=C2)C=C1)[Si](C)(C)C(C)(C)C	3415.3	Standard polar	33892256
dapsone hydroxylamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C2)C=C1	3715.0	Semi standard non polar	33892256
dapsone hydroxylamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C2)C=C1	3296.1	Standard non polar	33892256
dapsone hydroxylamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C2)C=C1	3434.2	Standard polar	33892256
dapsone hydroxylamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(O)C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1	3895.1	Semi standard non polar	33892256
dapsone hydroxylamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(O)C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1	3538.1	Standard non polar	33892256
dapsone hydroxylamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(O)C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1	3340.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - dapsone hydroxylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2930000000-963db6335e517b89cb9b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - dapsone hydroxylamine 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 - dapsone hydroxylamine 10V, Positive-QTOF	splash10-014j-0090000000-eddce420891c2cee706f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dapsone hydroxylamine 20V, Positive-QTOF	splash10-00ls-1090000000-8d51583ba3d5d8383156	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dapsone hydroxylamine 40V, Positive-QTOF	splash10-0bvl-9300000000-017a704e155958170002	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dapsone hydroxylamine 10V, Negative-QTOF	splash10-03di-0090000000-2a5f29cb14095d7f8711	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dapsone hydroxylamine 20V, Negative-QTOF	splash10-03di-0290000000-0e07acf82ab3bd4b0128	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dapsone hydroxylamine 40V, Negative-QTOF	splash10-052f-9700000000-2b318a7d7f05b49e79f3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dapsone hydroxylamine 10V, Positive-QTOF	splash10-014i-0090000000-e15fb6debf05a39ea7f9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dapsone hydroxylamine 20V, Positive-QTOF	splash10-014i-2290000000-2f83dfa064d8bfc346df	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dapsone hydroxylamine 40V, Positive-QTOF	splash10-0006-9200000000-cdc54638fd5f8540b766	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dapsone hydroxylamine 10V, Negative-QTOF	splash10-03di-0090000000-868502e8dd27a7fb9775	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dapsone hydroxylamine 20V, Negative-QTOF	splash10-03di-0090000000-868502e8dd27a7fb9775	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dapsone hydroxylamine 40V, Negative-QTOF	splash10-004i-4920000000-ed2b5d3795fb849a9171	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

65387

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 dapsone hydroxylamine (HMDB0060984)

MOL for HMDB0060984 (dapsone hydroxylamine)

3D MOL for HMDB0060984 (dapsone hydroxylamine)

3D SDF for HMDB0060984 (dapsone hydroxylamine)

3D-SDF for HMDB0060984 (dapsone hydroxylamine)

PDB for HMDB0060984 (dapsone hydroxylamine)

3D PDB for HMDB0060984 (dapsone hydroxylamine)

SMILES for HMDB0060984 (dapsone hydroxylamine)

INCHI for HMDB0060984 (dapsone hydroxylamine)

Structure for HMDB0060984 (dapsone hydroxylamine)

3D Structure for HMDB0060984 (dapsone hydroxylamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra