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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:13 UTC

Update Date

2020-02-26 21:39:08 UTC

HMDB ID

HMDB0013852

Secondary Accession Numbers

HMDB13852

Metabolite Identification

Common Name

Sulfamethoxazole N4-hydroxylamine

Description

Sulfamethoxazole N4-hydroxylamine, also known as SMX-HA or SMX-NHOH, belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. Sulfamethoxazole N4-hydroxylamine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Sulfamethoxazole N4-hydroxylamine.

Structure

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

HMDB0013852
     RDKit          3D
Sulfamethoxazole N4-hydroxylamine
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.9152    0.9241   -1.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7167    0.3051   -0.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3538    0.3828    0.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1768   -0.3260    0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4525   -0.5073    1.7574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095   -1.4120    1.8020 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.3222   -2.8140    1.2948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5194   -1.4866    3.2132 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342   -0.7376    0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1257    0.2208    1.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923    0.7106    0.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2057    0.2798   -0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2270    0.8126   -1.7377 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0843    1.7426   -1.2584 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311   -0.6630   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638   -1.1493   -0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8827   -0.7922   -0.6831 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7863   -0.4145   -1.5383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7249    0.1731   -1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2499    1.7855   -0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6593    1.2582   -2.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8980    0.9019    1.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091   -0.0760    2.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0097    0.5302    2.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7978    1.4623    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    0.4719   -2.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5948    1.3218   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -1.0059   -2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6726   -1.8989   -0.8726 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  1  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
  4 17  2  0
 17 18  1  0
 18  2  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
 10 24  1  0
 11 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
M  END

  Mrv0541 06151315542D          

 18 19  0  0  0  0            999 V2000
    9.8958   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2716   -6.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9662   -5.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6071   -5.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3017   -5.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5633   -2.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8958   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4511   -6.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1222   -5.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3083   -2.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1156   -7.3552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4834   -2.9195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7932   -3.5869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6005   -8.0226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7041   -4.0050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2114   -4.6761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2285   -2.1349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4577   -4.3406    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  1  1  0  0  0  0
  7  6  2  0  0  0  0
  8  2  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 17  7  1  0  0  0  0
 17 12  1  0  0  0  0
 18  9  1  0  0  0  0
 18 13  1  0  0  0  0
 18 15  2  0  0  0  0
 18 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013852

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(NS(=O)(=O)C2=CC=C(NO)C=C2)=NO1

> <INCHI_IDENTIFIER>
InChI=1S/C10H11N3O4S/c1-7-6-10(12-17-7)13-18(15,16)9-4-2-8(11-14)3-5-9/h2-6,11,14H,1H3,(H,12,13)

> <INCHI_KEY>
MJAMPGKHIZXVFJ-UHFFFAOYSA-N

> <FORMULA>
C10H11N3O4S

> <MOLECULAR_WEIGHT>
269.277

> <EXACT_MASS>
269.047026545

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
25.263037191144907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(hydroxyamino)-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
1.1277452613333332

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.01933973058098

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.065392102868645

> <JCHEM_PKA_STRONGEST_BASIC>
3.4078808900161452

> <JCHEM_POLAR_SURFACE_AREA>
104.46

> <JCHEM_REFRACTIVITY>
66.7826

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfamethoxazole hydroxylamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013852
     RDKit          3D
Sulfamethoxazole N4-hydroxylamine
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.9152    0.9241   -1.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7167    0.3051   -0.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3538    0.3828    0.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1768   -0.3260    0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4525   -0.5073    1.7574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095   -1.4120    1.8020 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.3222   -2.8140    1.2948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5194   -1.4866    3.2132 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342   -0.7376    0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1257    0.2208    1.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923    0.7106    0.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2057    0.2798   -0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2270    0.8126   -1.7377 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0843    1.7426   -1.2584 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311   -0.6630   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638   -1.1493   -0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8827   -0.7922   -0.6831 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7863   -0.4145   -1.5383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7249    0.1731   -1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2499    1.7855   -0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6593    1.2582   -2.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8980    0.9019    1.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091   -0.0760    2.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0097    0.5302    2.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7978    1.4623    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    0.4719   -2.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5948    1.3218   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -1.0059   -2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6726   -1.8989   -0.8726 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  1  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
  4 17  2  0
 17 18  1  0
 18  2  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
 10 24  1  0
 11 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0      18.472  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.174 -12.162   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.737 -11.077   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.800 -10.755   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.363  -9.670   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.718  -3.985   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.472  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.642 -12.323   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.895  -9.509   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.242  -5.450   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      17.016 -13.730   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      17.702  -5.450   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      20.147  -6.696   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      17.921 -14.976   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      18.114  -7.476   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      20.928  -8.729   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      17.227  -3.985   0.000  0.00  0.00           O+0
HETATM   18  S   UNK     0      19.521  -8.103   0.000  0.00  0.00           S+0
CONECT    1    7                                                            
CONECT    2    4    8                                                       
CONECT    3    5    8                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6    7   10                                                       
CONECT    7    1    6   17                                                  
CONECT    8    2    3   11                                                  
CONECT    9    4    5   18                                                  
CONECT   10    6   12   13                                                  
CONECT   11    8   14                                                       
CONECT   12   10   17                                                       
CONECT   13   10   18                                                       
CONECT   14   11                                                            
CONECT   15   18                                                            
CONECT   16   18                                                            
CONECT   17    7   12                                                       
CONECT   18    9   13   15   16                                             
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0060985
HETATM    1  C1  UNL     1       4.578   2.125  -0.850  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.521   1.220  -0.332  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.313  -0.103  -0.632  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.201  -0.545   0.091  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.654  -1.842   0.069  1.00  0.00           N  
HETATM    6  S1  UNL     1       0.289  -2.245   1.006  1.00  0.00           S  
HETATM    7  O1  UNL     1       0.540  -2.033   2.485  1.00  0.00           O  
HETATM    8  O2  UNL     1      -0.081  -3.700   0.856  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.131  -1.317   0.586  1.00  0.00           C  
HETATM   10  C6  UNL     1      -2.028  -1.734  -0.380  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.151  -0.991  -0.706  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.373   0.196  -0.041  1.00  0.00           C  
HETATM   13  N2  UNL     1      -4.503   1.013  -0.318  1.00  0.00           N  
HETATM   14  O3  UNL     1      -4.713   2.174   0.337  1.00  0.00           O  
HETATM   15  C9  UNL     1      -2.463   0.611   0.935  1.00  0.00           C  
HETATM   16  C10 UNL     1      -1.344  -0.131   1.257  1.00  0.00           C  
HETATM   17  N3  UNL     1       1.811   0.542   0.780  1.00  0.00           N  
HETATM   18  O4  UNL     1       2.579   1.555   0.529  1.00  0.00           O  
HETATM   19  H1  UNL     1       5.494   2.063  -0.226  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.843   1.822  -1.877  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.248   3.189  -0.846  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.930  -0.665  -1.317  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.091  -2.574  -0.533  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.855  -2.669  -0.906  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.861  -1.310  -1.463  1.00  0.00           H  
HETATM   26  H8  UNL     1      -5.189   0.726  -1.036  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.100   2.845  -0.041  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.622   1.536   1.463  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.678   0.244   2.022  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   18
CONECT    3    4   22
CONECT    4    5   17   17
CONECT    5    6   23
CONECT    6    7    7    8    8
CONECT    6    9
CONECT    9   10   10   16
CONECT   10   11   24
CONECT   11   12   12   25
CONECT   12   13   15
CONECT   13   14   26
CONECT   14   27
CONECT   15   16   16   28
CONECT   16   29
CONECT   17   18
END

HMDB0013852
     RDKit          3D
Sulfamethoxazole N4-hydroxylamine
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.9152    0.9241   -1.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7167    0.3051   -0.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3538    0.3828    0.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1768   -0.3260    0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4525   -0.5073    1.7574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095   -1.4120    1.8020 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.3222   -2.8140    1.2948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5194   -1.4866    3.2132 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342   -0.7376    0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1257    0.2208    1.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923    0.7106    0.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2057    0.2798   -0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2270    0.8126   -1.7377 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0843    1.7426   -1.2584 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311   -0.6630   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638   -1.1493   -0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8827   -0.7922   -0.6831 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7863   -0.4145   -1.5383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7249    0.1731   -1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2499    1.7855   -0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6593    1.2582   -2.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8980    0.9019    1.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091   -0.0760    2.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0097    0.5302    2.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7978    1.4623    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    0.4719   -2.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5948    1.3218   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -1.0059   -2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6726   -1.8989   -0.8726 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  1  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
  4 17  2  0
 17 18  1  0
 18  2  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
 10 24  1  0
 11 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(Hydroxyamino)-N-(5-methyl-3-isoxazolyl)benzenesulfonamide	ChEBI
SMX-HA	ChEBI
SMX-NHOH	ChEBI
4-(Hydroxyamino)-N-(5-methyl-3-isoxazolyl)benzenesulphonamide	Generator
Sulphamethoxazole N4-hydroxylamine	Generator
Sulphamethoxazole hydroxylamine	HMDB

Chemical Formula

C₁₀H₁₁N₃O₄S

Average Molecular Weight

269.277

Monoisotopic Molecular Weight

269.047026545

IUPAC Name

4-(hydroxyamino)-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide

Traditional Name

sulfamethoxazole hydroxylamine

CAS Registry Number

Not Available

SMILES

CC1=CC(NS(=O)(=O)C2=CC=C(NO)C=C2)=NO1

InChI Identifier

InChI=1S/C10H11N3O4S/c1-7-6-10(12-17-7)13-18(15,16)9-4-2-8(11-14)3-5-9/h2-6,11,14H,1H3,(H,12,13)

InChI Key

MJAMPGKHIZXVFJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
Benzenesulfonyl group
N-phenylhydroxylamine
1-hydroxylamino, 2-unsubstituted benzenoid
Arylhydroxamate
Organosulfonic acid amide
Imidolactam
Azole
Isoxazole
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Heteroaromatic compound
Sulfonyl
Aminosulfonyl compound
Oxacycle
Azacycle
N-organohydroxylamine
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:53016 )
isoxazoles (CHEBI:53016 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060985)

Organ

Kidney (HMDB: HMDB0060985)
Liver (HMDB: HMDB0060985)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060985)

Cellular substructure

Cytoplasm (HMDB: HMDB0060985)

Source

Endogenous

Endogenous (HMDB: HMDB0060985)

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	0.68 g/L	ALOGPS
logP	0.99	ALOGPS
logP	1.13	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.07	ChemAxon
pKa (Strongest Basic)	3.41	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	66.78 m³·mol⁻¹	ChemAxon
Polarizability	25.26 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]+	163.717	31661259
DarkChem	[M-H]-	163.275	31661259
DeepCCS	[M+H]+	154.215	30932474
DeepCCS	[M-H]-	151.857	30932474
DeepCCS	[M-2H]-	184.935	30932474
DeepCCS	[M+Na]+	160.308	30932474
AllCCS	[M+H]+	160.9	32859911
AllCCS	[M+H-H2O]+	157.2	32859911
AllCCS	[M+NH4]+	164.3	32859911
AllCCS	[M+Na]+	165.3	32859911
AllCCS	[M-H]-	157.0	32859911
AllCCS	[M+Na-2H]-	156.9	32859911
AllCCS	[M+HCOO]-	157.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sulfamethoxazole N4-hydroxylamine	CC1=CC(NS(=O)(=O)C2=CC=C(NO)C=C2)=NO1	4005.5	Standard polar	33892256
Sulfamethoxazole N4-hydroxylamine	CC1=CC(NS(=O)(=O)C2=CC=C(NO)C=C2)=NO1	2557.8	Standard non polar	33892256
Sulfamethoxazole N4-hydroxylamine	CC1=CC(NS(=O)(=O)C2=CC=C(NO)C=C2)=NO1	2625.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sulfamethoxazole N4-hydroxylamine,1TMS,isomer #1	CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(NO)C=C2)=NO1	2614.3	Semi standard non polar	33892256
Sulfamethoxazole N4-hydroxylamine,1TMS,isomer #1	CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(NO)C=C2)=NO1	2571.4	Standard non polar	33892256
Sulfamethoxazole N4-hydroxylamine,1TMS,isomer #1	CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(NO)C=C2)=NO1	3835.1	Standard polar	33892256
Sulfamethoxazole N4-hydroxylamine,1TMS,isomer #2	CC1=CC(NS(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C)C=C2)=NO1	2736.2	Semi standard non polar	33892256
Sulfamethoxazole N4-hydroxylamine,1TMS,isomer #2	CC1=CC(NS(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C)C=C2)=NO1	2559.5	Standard non polar	33892256
Sulfamethoxazole N4-hydroxylamine,1TMS,isomer #2	CC1=CC(NS(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C)C=C2)=NO1	3991.5	Standard polar	33892256
Sulfamethoxazole N4-hydroxylamine,2TMS,isomer #1	CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C)C=C2)=NO1	2504.8	Semi standard non polar	33892256
Sulfamethoxazole N4-hydroxylamine,2TMS,isomer #1	CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C)C=C2)=NO1	2615.6	Standard non polar	33892256
Sulfamethoxazole N4-hydroxylamine,2TMS,isomer #1	CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C)C=C2)=NO1	3456.8	Standard polar	33892256
Sulfamethoxazole N4-hydroxylamine,1TBDMS,isomer #1	CC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(NO)C=C2)=NO1	2904.9	Semi standard non polar	33892256
Sulfamethoxazole N4-hydroxylamine,1TBDMS,isomer #1	CC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(NO)C=C2)=NO1	2813.4	Standard non polar	33892256
Sulfamethoxazole N4-hydroxylamine,1TBDMS,isomer #1	CC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(NO)C=C2)=NO1	3777.7	Standard polar	33892256
Sulfamethoxazole N4-hydroxylamine,1TBDMS,isomer #2	CC1=CC(NS(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C2)=NO1	3012.3	Semi standard non polar	33892256
Sulfamethoxazole N4-hydroxylamine,1TBDMS,isomer #2	CC1=CC(NS(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C2)=NO1	2759.9	Standard non polar	33892256
Sulfamethoxazole N4-hydroxylamine,1TBDMS,isomer #2	CC1=CC(NS(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C2)=NO1	3943.9	Standard polar	33892256
Sulfamethoxazole N4-hydroxylamine,2TBDMS,isomer #1	CC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C2)=NO1	3038.0	Semi standard non polar	33892256
Sulfamethoxazole N4-hydroxylamine,2TBDMS,isomer #1	CC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C2)=NO1	3045.4	Standard non polar	33892256
Sulfamethoxazole N4-hydroxylamine,2TBDMS,isomer #1	CC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N(O)[Si](C)(C)C(C)(C)C)C=C2)=NO1	3512.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Sulfamethoxazole N4-hydroxylamine EI-B (Non-derivatized)	splash10-0006-9000000000-17d6216bbb70ae5eb57d	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfamethoxazole N4-hydroxylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9440000000-94f20d3af55fb47fdbe4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfamethoxazole N4-hydroxylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfamethoxazole N4-hydroxylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfamethoxazole N4-hydroxylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-ac6c25bdfcc90fb4d9db	2018-05-25	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethoxazole N4-hydroxylamine 10V, Positive-QTOF	splash10-00di-0690000000-7c41d3161282cca77b88	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethoxazole N4-hydroxylamine 20V, Positive-QTOF	splash10-00di-4930000000-8a0ffd2a93ab4725171d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethoxazole N4-hydroxylamine 40V, Positive-QTOF	splash10-0a4i-7900000000-ea5f0596ab6b704c7df6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethoxazole N4-hydroxylamine 10V, Negative-QTOF	splash10-014i-0090000000-3444522061f774adac8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethoxazole N4-hydroxylamine 20V, Negative-QTOF	splash10-014i-4390000000-df6cd36c078b59b3a66b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethoxazole N4-hydroxylamine 40V, Negative-QTOF	splash10-0a4i-9840000000-d61e3d47f2b95e1a8a13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethoxazole N4-hydroxylamine 10V, Negative-QTOF	splash10-014i-0090000000-669a7a7aa5a645bd1942	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethoxazole N4-hydroxylamine 20V, Negative-QTOF	splash10-014i-2190000000-65ba072d60b700b82b35	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethoxazole N4-hydroxylamine 40V, Negative-QTOF	splash10-01c1-9530000000-9ae1b06b0de60bf2537d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethoxazole N4-hydroxylamine 10V, Positive-QTOF	splash10-00di-0290000000-c2985b0b9b8ae7444196	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethoxazole N4-hydroxylamine 20V, Positive-QTOF	splash10-00di-0930000000-14102d852f23a5b34e16	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamethoxazole N4-hydroxylamine 40V, Positive-QTOF	splash10-0aor-9500000000-d982a37e04f925c2906e	2021-09-22	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

FDB000755

KNApSAcK ID

Not Available

Chemspider ID

102783

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

114821

PDB ID

Not Available

ChEBI ID

53016

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 Sulfamethoxazole N4-hydroxylamine (HMDB0013852)

MOL for HMDB0013852 (Sulfamethoxazole N4-hydroxylamine)

3D MOL for HMDB0013852 (Sulfamethoxazole N4-hydroxylamine)

3D SDF for HMDB0013852 (Sulfamethoxazole N4-hydroxylamine)

3D-SDF for HMDB0013852 (Sulfamethoxazole N4-hydroxylamine)

PDB for HMDB0013852 (Sulfamethoxazole N4-hydroxylamine)

3D PDB for HMDB0013852 (Sulfamethoxazole N4-hydroxylamine)

SMILES for HMDB0013852 (Sulfamethoxazole N4-hydroxylamine)

INCHI for HMDB0013852 (Sulfamethoxazole N4-hydroxylamine)

Structure for HMDB0013852 (Sulfamethoxazole N4-hydroxylamine)

3D Structure for HMDB0013852 (Sulfamethoxazole N4-hydroxylamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra