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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014395

Secondary Accession Numbers

HMDB14395

Metabolite Identification

Common Name

Dapsone

Description

Dapsone, also known as diaphenylsulfone or 4,4'-dapsone, 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. Dapsone is a drug which is used for the treatment and management of leprosy and dermatitis herpetiformis. Based on a literature review a significant number of articles have been published on Dapsone.

Structure

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

HMDB0014395
     RDKit          3D
Dapsone
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.7744    1.4765   -0.3677 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6286    0.7359    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2033   -0.3088   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0856   -1.0316   -0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4132   -0.7005    0.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0177   -1.6023    1.2666 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.1392   -1.5232    2.7577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1351   -3.0058    0.7822 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170   -0.8354    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0711    0.1565    1.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1807    0.7764    0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6267    0.3748   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580    0.9977   -1.1032 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9568   -0.6290   -1.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456   -1.2605   -0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8236    0.3462    1.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503    1.0599    1.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8615    1.7040   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4957    1.7846    0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7067   -0.5853   -1.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105   -1.8649   -0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7260    0.4914    2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6738    1.5659    1.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4789    1.3926   -0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8508    1.0509   -2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2777   -0.9834   -2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102   -2.0509   -1.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2754    0.5815    2.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665    1.8864    1.8257 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
 12 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 17  2  1  0
 15  9  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
 10 22  1  0
 11 23  1  0
 13 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END


  Mrv1652305271900082D          

 17 18  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
    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
 17 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 15  2  0  0  0  0
 17 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014395

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(N)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2

> <INCHI_KEY>
MQJKPEGWNLWLTK-UHFFFAOYSA-N

> <FORMULA>
C12H12N2O2S

> <MOLECULAR_WEIGHT>
248.301

> <EXACT_MASS>
248.061948328

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.050311165926733

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(4-aminobenzenesulfonyl)aniline

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
1.2702285519999998

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.391712007947518

> <JCHEM_POLAR_SURFACE_AREA>
86.17999999999999

> <JCHEM_REFRACTIVITY>
68.99100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dapsone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014395
     RDKit          3D
Dapsone
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.7744    1.4765   -0.3677 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6286    0.7359    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2033   -0.3088   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0856   -1.0316   -0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4132   -0.7005    0.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0177   -1.6023    1.2666 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.1392   -1.5232    2.7577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1351   -3.0058    0.7822 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170   -0.8354    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0711    0.1565    1.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1807    0.7764    0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6267    0.3748   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580    0.9977   -1.1032 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9568   -0.6290   -1.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456   -1.2605   -0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8236    0.3462    1.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503    1.0599    1.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8615    1.7040   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4957    1.7846    0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7067   -0.5853   -1.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105   -1.8649   -0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7260    0.4914    2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6738    1.5659    1.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4789    1.3926   -0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8508    1.0509   -2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2777   -0.9834   -2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102   -2.0509   -1.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2754    0.5815    2.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665    1.8864    1.8257 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
 12 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 17  2  1  0
 15  9  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
 10 22  1  0
 11 23  1  0
 13 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         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       8.208   0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.128   0.770   0.000  0.00  0.00           O+0
HETATM   17  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   17                                                  
CONECT   12    7    8   17                                                  
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15   17                                                            
CONECT   16   17                                                            
CONECT   17   11   12   15   16                                             
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0014395
HETATM    1  N1  UNL     1      -4.774   1.477  -0.368  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.629   0.736   0.018  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.203  -0.309  -0.777  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.086  -1.032  -0.401  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.413  -0.700   0.757  1.00  0.00           C  
HETATM    6  S1  UNL     1       0.018  -1.602   1.267  1.00  0.00           S  
HETATM    7  O1  UNL     1       0.139  -1.523   2.758  1.00  0.00           O  
HETATM    8  O2  UNL     1      -0.135  -3.006   0.782  1.00  0.00           O  
HETATM    9  C5  UNL     1       1.417  -0.835   0.566  1.00  0.00           C  
HETATM   10  C6  UNL     1       2.071   0.157   1.232  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.181   0.776   0.694  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.627   0.375  -0.541  1.00  0.00           C  
HETATM   13  N2  UNL     1       4.758   0.998  -1.103  1.00  0.00           N  
HETATM   14  C9  UNL     1       2.957  -0.629  -1.204  1.00  0.00           C  
HETATM   15  C10 UNL     1       1.846  -1.261  -0.683  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.824   0.346   1.571  1.00  0.00           C  
HETATM   17  C12 UNL     1      -2.950   1.060   1.174  1.00  0.00           C  
HETATM   18  H1  UNL     1      -4.861   1.704  -1.389  1.00  0.00           H  
HETATM   19  H2  UNL     1      -5.496   1.785   0.306  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.707  -0.585  -1.679  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.710  -1.865  -0.995  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.726   0.491   2.226  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.674   1.566   1.262  1.00  0.00           H  
HETATM   24  H7  UNL     1       5.479   1.393  -0.472  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.851   1.051  -2.134  1.00  0.00           H  
HETATM   26  H9  UNL     1       3.278  -0.983  -2.196  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.310  -2.051  -1.194  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.275   0.582   2.473  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.267   1.886   1.826  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3    3   17
CONECT    3    4   20
CONECT    4    5    5   21
CONECT    5    6   16
CONECT    6    7    7    8    8
CONECT    6    9
CONECT    9   10   10   15
CONECT   10   11   22
CONECT   11   12   12   23
CONECT   12   13   14
CONECT   13   24   25
CONECT   14   15   15   26
CONECT   15   27
CONECT   16   17   17   28
CONECT   17   29
END

HMDB0014395
     RDKit          3D
Dapsone
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.7744    1.4765   -0.3677 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6286    0.7359    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2033   -0.3088   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0856   -1.0316   -0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4132   -0.7005    0.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0177   -1.6023    1.2666 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.1392   -1.5232    2.7577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1351   -3.0058    0.7822 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170   -0.8354    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0711    0.1565    1.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1807    0.7764    0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6267    0.3748   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580    0.9977   -1.1032 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9568   -0.6290   -1.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456   -1.2605   -0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8236    0.3462    1.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503    1.0599    1.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8615    1.7040   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4957    1.7846    0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7067   -0.5853   -1.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105   -1.8649   -0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7260    0.4914    2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6738    1.5659    1.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4789    1.3926   -0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8508    1.0509   -2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2777   -0.9834   -2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102   -2.0509   -1.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2754    0.5815    2.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665    1.8864    1.8257 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
 12 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 17  2  1  0
 15  9  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
 10 22  1  0
 11 23  1  0
 13 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,1'-Sulfonylbis(4-aminobenzene)	ChEBI
4,4'-Dapsone	ChEBI
4,4'-Diaminodiphenyl sulfone	ChEBI
4,4'-Sulfonylbisaniline	ChEBI
4,4'-Sulfonylbisbenzenamine	ChEBI
4-(4-Amino-benzenesulfonyl)-phenylamine	ChEBI
4-(4-Aminophenylsulfonyl)aniline	ChEBI
4-(4-Aminophenylsulfonyl)benzenamine	ChEBI
4-Aminophenyl sulfone	ChEBI
Bis(4-aminophenyl)sulfone	ChEBI
Bis(p-aminophenyl) sulfone	ChEBI
DADPS	ChEBI
Dapsona	ChEBI
Dapsonum	ChEBI
DDS	ChEBI
DIAPHENYLsulfone	ChEBI
p,P'-diaminodiphenyl sulfone	ChEBI
p,p-Sulphonylbisbenzamine	ChEBI
p,p-Sulphonylbisbenzenamine	ChEBI
p-Aminophenyl sulfone	ChEBI
Aczone	Kegg
1,1'-Sulphonylbis(4-aminobenzene)	Generator
4,4'-Diaminodiphenyl sulphone	Generator
4,4'-Sulphonylbisaniline	Generator
4,4'-Sulphonylbisbenzenamine	Generator
4-(4-Amino-benzenesulphonyl)-phenylamine	Generator
4-(4-Aminophenylsulphonyl)aniline	Generator
4-(4-Aminophenylsulphonyl)benzenamine	Generator
4-Aminophenyl sulphone	Generator
Bis(4-aminophenyl)sulphone	Generator
Bis(p-aminophenyl) sulphone	Generator
DIAPHENYLsulphone	Generator
p,P'-diaminodiphenyl sulphone	Generator
p,p-Sulfonylbisbenzamine	Generator
p,p-Sulfonylbisbenzenamine	Generator
p-Aminophenyl sulphone	Generator
1,1'-Sulfonylbis[4-aminobenzene]	HMDB
4,4'-Diaminodiphenylsulfone	HMDB
4,4'-Sulfonylbisbenzeneamine	HMDB
4,4'-Sulfonyldianilin	HMDB
4,4'-Sulfonyldianiline	HMDB
DDS, Pharmaceutical	HMDB
Mex-america brand OF dapsone	HMDB
Sulfona	HMDB
4,4' Diaminophenyl sulfone	HMDB
4,4'-Diaminophenyl sulfone	HMDB
Dapson-fatol	HMDB
Disulone	HMDB
Fatol brand OF dapsone	HMDB
Orsade brand OF dapsone	HMDB
Sulfone, 4,4'-diaminophenyl	HMDB
Sulfonyldianiline	HMDB
Avlosulfone	HMDB
Dapsoderm-X	HMDB
Diaminodiphenylsulfone	HMDB

Chemical Formula

C₁₂H₁₂N₂O₂S

Average Molecular Weight

248.301

Monoisotopic Molecular Weight

248.061948328

IUPAC Name

4-(4-aminobenzenesulfonyl)aniline

Traditional Name

dapsone

CAS Registry Number

80-08-0

SMILES

NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(N)C=C1

InChI Identifier

InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2

InChI Key

MQJKPEGWNLWLTK-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
Aniline or substituted anilines
Sulfonyl
Sulfone
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

sulfone (CHEBI:4325 )
substituted aniline (CHEBI:4325 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	175.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.28 g/L	Not Available
LogP	0.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	151.709	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000800

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	1.19	ALOGPS
logP	1.27	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	2.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.18 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.99 m³·mol⁻¹	ChemAxon
Polarizability	25.05 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]+	157.129	31661259
DarkChem	[M-H]-	158.976	31661259
DeepCCS	[M+H]+	163.225	30932474
DeepCCS	[M-H]-	160.867	30932474
DeepCCS	[M-2H]-	193.821	30932474
DeepCCS	[M+Na]+	169.318	30932474
AllCCS	[M+H]+	157.3	32859911
AllCCS	[M+H-H2O]+	153.5	32859911
AllCCS	[M+NH4]+	160.8	32859911
AllCCS	[M+Na]+	161.8	32859911
AllCCS	[M-H]-	154.0	32859911
AllCCS	[M+Na-2H]-	154.0	32859911
AllCCS	[M+HCOO]-	154.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dapsone	NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(N)C=C1	4492.4	Standard polar	33892256
Dapsone	NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(N)C=C1	2901.0	Standard non polar	33892256
Dapsone	NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(N)C=C1	2873.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dapsone,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1	2961.1	Semi standard non polar	33892256
Dapsone,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1	2654.9	Standard non polar	33892256
Dapsone,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1	3591.3	Standard polar	33892256
Dapsone,2TMS,isomer #1	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)C=C1	3233.8	Semi standard non polar	33892256
Dapsone,2TMS,isomer #1	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)C=C1	2783.6	Standard non polar	33892256
Dapsone,2TMS,isomer #1	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)C=C1	3104.2	Standard polar	33892256
Dapsone,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C	2956.2	Semi standard non polar	33892256
Dapsone,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C	2706.0	Standard non polar	33892256
Dapsone,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C	3376.8	Standard polar	33892256
Dapsone,3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1	3149.4	Semi standard non polar	33892256
Dapsone,3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1	2813.2	Standard non polar	33892256
Dapsone,3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1	2936.7	Standard polar	33892256
Dapsone,4TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1)[Si](C)(C)C	3080.4	Semi standard non polar	33892256
Dapsone,4TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1)[Si](C)(C)C	2886.7	Standard non polar	33892256
Dapsone,4TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1)[Si](C)(C)C	2743.8	Standard polar	33892256
Dapsone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1	3217.7	Semi standard non polar	33892256
Dapsone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1	2899.3	Standard non polar	33892256
Dapsone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1	3600.8	Standard polar	33892256
Dapsone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C=C1	3718.3	Semi standard non polar	33892256
Dapsone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C=C1	3236.5	Standard non polar	33892256
Dapsone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C=C1	3216.9	Standard polar	33892256
Dapsone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C(C)(C)C	3481.4	Semi standard non polar	33892256
Dapsone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C(C)(C)C	3146.8	Standard non polar	33892256
Dapsone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C(C)(C)C	3383.3	Standard polar	33892256
Dapsone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=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	3898.1	Semi standard non polar	33892256
Dapsone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=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	3450.6	Standard non polar	33892256
Dapsone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=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	3148.5	Standard polar	33892256
Dapsone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(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)[Si](C)(C)C(C)(C)C	3996.1	Semi standard non polar	33892256
Dapsone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(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)[Si](C)(C)C(C)(C)C	3734.5	Standard non polar	33892256
Dapsone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(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)[Si](C)(C)C(C)(C)C	3042.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dapsone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0564-9770000000-98d678eb70ae9cdbbfaa	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dapsone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052g-8930000000-c51783649020dadfb20f	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-qTof , Positive-QTOF	splash10-0a4i-5901100000-901603cf86087b4a4abb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QQ , negative-QTOF	splash10-0002-0190000000-7de0f1aeb77cf9b122f5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QQ , negative-QTOF	splash10-0002-0290000000-f1e61c46f1720875a177	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QQ , negative-QTOF	splash10-0a4i-0920000000-ed66532a51b7d047462a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QQ , negative-QTOF	splash10-0a4l-3900000000-a1f636a2e557bc9b69a5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QQ , negative-QTOF	splash10-052f-9800000000-3557ad8246dc0a0aa05c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QTOF , positive-QTOF	splash10-0a4i-5910000000-0c8eb03605a271970f1d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOF	splash10-052b-0590000000-a23b099ad5d2d3cd716d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOF	splash10-0a4i-1920000000-0260de715fec538fe8bb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOF	splash10-0a4l-5900000000-6ba41fa3598abafdb242	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOF	splash10-052f-9600000000-d2fe4c5ba425499ba98c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOF	splash10-052f-9400000000-e29e2bdac763fc5e250b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOF	splash10-066u-9200000000-71494cee2792628e6a0c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOF	splash10-014i-9000000000-38433ad894a5e08f6ee0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOF	splash10-014i-9000000000-e4782e47ceb05d1ffbda	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QFT , positive-QTOF	splash10-014i-9000000000-4ab9019e60b1718d1d29	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QQ , positive-QTOF	splash10-0002-0190000000-d7cf0928be57fafd7ea4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QQ , positive-QTOF	splash10-0a4i-1930000000-09cf0e392eeef139f2b1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dapsone LC-ESI-QQ , positive-QTOF	splash10-0a4l-8900000000-5da3a6d058cb14fc8300	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapsone 10V, Positive-QTOF	splash10-0002-0090000000-77f73a73b1a222285be3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapsone 20V, Positive-QTOF	splash10-0002-0090000000-efb6858364a1d7c22428	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapsone 40V, Positive-QTOF	splash10-004i-9430000000-d9c6fe280d40d0bc8dd6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapsone 10V, Negative-QTOF	splash10-0002-0090000000-f3d8a4bdccbe1170ae6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapsone 20V, Negative-QTOF	splash10-0002-0090000000-ab2b74cff1f89de7c9a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapsone 40V, Negative-QTOF	splash10-0006-9020000000-d4698e6b7c05ce3e71e6	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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 DB00250	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00250	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00250

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2849

KEGG Compound ID

C07666

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dapsone

METLIN ID

Not Available

PubChem Compound

2955

PDB ID

Not Available

ChEBI ID

4325

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1198951

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Malfara WR, Pereira CP, Santos AC, Queiroz RH: Effects of H(2)-receptor antagonists on dapsone-induced methaemoglobinaemia in rats. Pharmacol Res. 2002 Apr;45(4):269-73. [PubMed:12030789 ]
FLOCH H, GELARD AM: [Study of 4,4'-bis(ethylamino)-diphenylsulfone and of N-succinyl-4,4'diaminodiphenylsulfone administered intramuscularly in depot form]. Publ Inst Pasteur Guyane Fr Inini. 1954 Oct;15(343):1-7. [PubMed:14377653 ]

Showing metabocard for Dapsone (HMDB0014395)

MOL for HMDB0014395 (Dapsone)

3D MOL for HMDB0014395 (Dapsone)

3D SDF for HMDB0014395 (Dapsone)

3D-SDF for HMDB0014395 (Dapsone)

PDB for HMDB0014395 (Dapsone)

3D PDB for HMDB0014395 (Dapsone)

SMILES for HMDB0014395 (Dapsone)

INCHI for HMDB0014395 (Dapsone)

Structure for HMDB0014395 (Dapsone)

3D Structure for HMDB0014395 (Dapsone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra