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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:14 UTC

Update Date

2020-07-06 16:00:59 UTC

HMDB ID

HMDB0013854

Secondary Accession Numbers

HMDB13854

Metabolite Identification

Common Name

N4-Acetylsulfamethoxazole

Description

N4-Acetylsulfamethoxazole is a metabolite of the sulfonamide bacteriostatic antibiotic sulfamethoxazole. Sulfamethoxazole is metabolized via acetylation catalyzed by liver extramitochondrial N-acetyl transferases. Acetylsulfamethoxazole is excreted in urine. Acetylsulfamethoxazole and sulfamethoxazole can be used as a probe for the molecular percentage enrichment of liver extramitochondrial acetyl-CoA. N4-Acetylsulfamethoxazole can be used as a reference for measuring sulfamethoxazole impurities and waste determination (PMID: 15307787 ). It is one of the critical aspects of urine and stone analysis (PMID: 3811034 ) and its quantitative determination in body fluids could be performed by reversed-phase high-performance liquid chromatography, a rapid, precise and simple procedure (PMID: 6668314 ). It is also reported the renal excretion rate of the metabolite N4-acetylsulfamethoxazole is not dependent on the urinary pH (PMID: 670346 ). N4-Acetylsulfamethoxazole is only found in individuals who have consumed the drug sulfamethoxazole.

Structure

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

HMDB0013854
     RDKit          3D
N4-Acetylsulfamethoxazole
 33 34  0  0  0  0  0  0  0  0999 V2000
    2.9875   -1.9259   -0.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0892   -1.0738   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3963   -1.5388   -0.0717 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8883    0.1115    0.4257 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5960    0.6982    0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6252    0.1038    1.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3450    0.6628    1.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    1.8176    0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5938    2.5190    0.8412 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.2979    2.0558    2.0979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969    4.0312    0.9939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6082    2.1221   -0.4798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0156    0.8158   -0.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7480   -0.4056   -0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4031   -1.3962   -0.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749   -2.8513   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0081   -0.7630   -1.9347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8207    0.5108   -1.8923 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9893    2.4130   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2482    1.8573   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3284   -2.6650   -1.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -2.5194    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2422   -1.2667   -1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0334   -1.0174   -0.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8436   -0.7935    1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4073    0.1803    2.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9586    2.9121   -1.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1465   -0.5619    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8234   -3.3582   -1.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8060   -3.0591    0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3925   -3.2683   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7120    3.3296   -0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155    2.3233   -0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  8 19  1  0
 19 20  2  0
 20  5  1  0
 18 13  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  0
  7 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
M  END


  Mrv0541 08281313192D          

 20 21  0  0  0  0            999 V2000
    4.1801    1.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2437   -5.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5557   -4.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2504   -3.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8914   -3.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5859   -2.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476    0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5793   -5.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7353   -4.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4064   -2.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5926   -0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3998   -5.0652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7676   -0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0775   -1.2968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0943   -4.4840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9883   -1.7149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127    0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7420   -2.0505    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  1  1  0  0  0  0
  8  7  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  1  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  4  0  0  0
 14 12  2  0  0  0  0
 15 12  1  0  0  0  0
 16  9  1  0  0  0  0
 19  8  1  0  0  0  0
 19 14  1  0  0  0  0
 20 11  1  0  0  0  0
 20 15  1  0  0  0  0
 20 17  2  0  0  0  0
 20 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013854

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H13N3O4S/c1-8-7-12(14-19-8)15-20(17,18)11-5-3-10(4-6-11)13-9(2)16/h3-7H,1-2H3,(H,13,16)(H,14,15)

> <INCHI_KEY>
GXPIUNZCALHVBA-UHFFFAOYSA-N

> <FORMULA>
C12H13N3O4S

> <MOLECULAR_WEIGHT>
295.314

> <EXACT_MASS>
295.062676609

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.51313355629874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}ethanimidic acid

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
1.5846423903333329

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.344430938756576

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.6811164080854475

> <JCHEM_PKA_STRONGEST_BASIC>
0.7811028519200727

> <JCHEM_POLAR_SURFACE_AREA>
104.79

> <JCHEM_REFRACTIVITY>
75.41349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N(sup 4)-acetylsulfisomezole

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013854
     RDKit          3D
N4-Acetylsulfamethoxazole
 33 34  0  0  0  0  0  0  0  0999 V2000
    2.9875   -1.9259   -0.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0892   -1.0738   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3963   -1.5388   -0.0717 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8883    0.1115    0.4257 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5960    0.6982    0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6252    0.1038    1.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3450    0.6628    1.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    1.8176    0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5938    2.5190    0.8412 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.2979    2.0558    2.0979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969    4.0312    0.9939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6082    2.1221   -0.4798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0156    0.8158   -0.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7480   -0.4056   -0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4031   -1.3962   -0.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749   -2.8513   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0081   -0.7630   -1.9347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8207    0.5108   -1.8923 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9893    2.4130   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2482    1.8573   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3284   -2.6650   -1.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -2.5194    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2422   -1.2667   -1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0334   -1.0174   -0.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8436   -0.7935    1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4073    0.1803    2.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9586    2.9121   -1.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1465   -0.5619    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8234   -3.3582   -1.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8060   -3.0591    0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3925   -3.2683   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7120    3.3296   -0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155    2.3233   -0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  8 19  1  0
 19 20  2  0
 20  5  1  0
 18 13  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  0
  7 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
M  END

HEADER    PROTEIN                                 28-AUG-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-AUG-13         0                                  
HETATM    1  C   UNK     0       7.803   2.735   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.188 -11.023   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.504  -7.887   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.067  -6.802   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.131  -6.480   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.694  -5.395   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.049   0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.803   1.195   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.815  -9.616   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.973  -8.048   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.225  -5.234   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.573  -1.175   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.346  -9.455   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       7.033  -1.175   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       9.478  -2.421   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       3.909  -8.370   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.445  -3.201   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.259  -4.454   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.557   0.290   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0       8.852  -3.828   0.000  0.00  0.00           S+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    5   10                                                       
CONECT    4    6   10                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    8   12                                                       
CONECT    8    1    7   19                                                  
CONECT    9    2   13   16                                                  
CONECT   10    3    4   13                                                  
CONECT   11    5    6   20                                                  
CONECT   12    7   14   15                                                  
CONECT   13    9   10                                                       
CONECT   14   12   19                                                       
CONECT   15   12   20                                                       
CONECT   16    9                                                            
CONECT   17   20                                                            
CONECT   18   20                                                            
CONECT   19    8   14                                                       
CONECT   20   11   15   17   18                                             
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0013854
HETATM    1  C1  UNL     1       2.987  -1.926  -0.512  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.089  -1.074  -0.035  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.396  -1.539  -0.072  1.00  0.00           O  
HETATM    4  N1  UNL     1       3.888   0.111   0.426  1.00  0.00           N  
HETATM    5  C3  UNL     1       2.596   0.698   0.514  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.625   0.104   1.290  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.345   0.663   1.393  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.001   1.818   0.731  1.00  0.00           C  
HETATM    9  S1  UNL     1      -1.594   2.519   0.841  1.00  0.00           S  
HETATM   10  O2  UNL     1      -2.298   2.056   2.098  1.00  0.00           O  
HETATM   11  O3  UNL     1      -1.497   4.031   0.994  1.00  0.00           O  
HETATM   12  N2  UNL     1      -2.608   2.122  -0.480  1.00  0.00           N  
HETATM   13  C7  UNL     1      -3.016   0.816  -0.831  1.00  0.00           C  
HETATM   14  C8  UNL     1      -2.748  -0.406  -0.253  1.00  0.00           C  
HETATM   15  C9  UNL     1      -3.403  -1.396  -0.991  1.00  0.00           C  
HETATM   16  C10 UNL     1      -3.375  -2.851  -0.704  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.008  -0.763  -1.935  1.00  0.00           O  
HETATM   18  N3  UNL     1      -3.821   0.511  -1.892  1.00  0.00           N  
HETATM   19  C11 UNL     1       0.989   2.413  -0.053  1.00  0.00           C  
HETATM   20  C12 UNL     1       2.248   1.857  -0.149  1.00  0.00           C  
HETATM   21  H1  UNL     1       3.328  -2.665  -1.273  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.560  -2.519   0.317  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.242  -1.267  -1.005  1.00  0.00           H  
HETATM   24  H4  UNL     1       6.033  -1.017  -0.684  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.844  -0.794   1.823  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.407   0.180   2.019  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.959   2.912  -1.082  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.146  -0.562   0.609  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.823  -3.358  -1.527  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.806  -3.059   0.225  1.00  0.00           H  
HETATM   31  H11 UNL     1      -4.392  -3.268  -0.552  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.712   3.330  -0.576  1.00  0.00           H  
HETATM   33  H13 UNL     1       3.015   2.323  -0.760  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4    4
CONECT    3   24
CONECT    4    5
CONECT    5    6    6   20
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   19
CONECT    9   10   10   11   11
CONECT    9   12
CONECT   12   13   27
CONECT   13   14   18   18
CONECT   14   15   15   28
CONECT   15   16   17
CONECT   16   29   30   31
CONECT   17   18
CONECT   19   20   20   32
CONECT   20   33
END

HMDB0013854
     RDKit          3D
N4-Acetylsulfamethoxazole
 33 34  0  0  0  0  0  0  0  0999 V2000
    2.9875   -1.9259   -0.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0892   -1.0738   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3963   -1.5388   -0.0717 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8883    0.1115    0.4257 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5960    0.6982    0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6252    0.1038    1.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3450    0.6628    1.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    1.8176    0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5938    2.5190    0.8412 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.2979    2.0558    2.0979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969    4.0312    0.9939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6082    2.1221   -0.4798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0156    0.8158   -0.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7480   -0.4056   -0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4031   -1.3962   -0.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749   -2.8513   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0081   -0.7630   -1.9347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8207    0.5108   -1.8923 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9893    2.4130   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2482    1.8573   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3284   -2.6650   -1.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -2.5194    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2422   -1.2667   -1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0334   -1.0174   -0.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8436   -0.7935    1.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4073    0.1803    2.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9586    2.9121   -1.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1465   -0.5619    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8234   -3.3582   -1.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8060   -3.0591    0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3925   -3.2683   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7120    3.3296   -0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155    2.3233   -0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  8 19  1  0
 19 20  2  0
 20  5  1  0
 18 13  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  0
  7 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4'-((5-Methyl-3-isoxazolyl)sulfamoyl)acetanilide	ChEBI
Acetylsulfamethoxazole	ChEBI
Gantanol	ChEBI
N(4)-Acetylsulfisomezole	ChEBI
N(4)-Acetylsulfulfamethoxazole	ChEBI
SMX-Acetate	ChEBI
Sulfamethoxazole acetate	ChEBI
Sulfisomezole-N(4)-acetate	ChEBI
4'-((5-Methyl-3-isoxazolyl)sulphamoyl)acetanilide	Generator
Acetylsulphamethoxazole	Generator
N(4)-Acetylsulphisomezole	Generator
N(4)-Acetylsulphulfamethoxazole	Generator
SMX-Acetic acid	Generator
Sulfamethoxazole acetic acid	Generator
Sulphamethoxazole acetate	Generator
Sulphamethoxazole acetic acid	Generator
Sulfisomezole-N(4)-acetic acid	Generator
Sulphisomezole-N(4)-acetate	Generator
Sulphisomezole-N(4)-acetic acid	Generator
N4-Acetylsulphamethoxazole	Generator
N-{4-[(5-methylisoxazol-3-yl)sulfamoyl]phenyl}acetamide	HMDB
N4-Acetylsulfisomezole	HMDB
N4-Acetylsulfulfamethoxazole	HMDB
Sulfisomezole-N4-acetate	HMDB
N(4)-Acetylsulfamethoxazole	HMDB
N(4)-Acetylsulphamethoxazole	HMDB
N-Acetylsulphamethoxazole	HMDB
N4-Acetylsulfamethoxazole	ChEBI

Chemical Formula

C₁₂H₁₃N₃O₄S

Average Molecular Weight

295.314

Monoisotopic Molecular Weight

295.062676609

IUPAC Name

N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}ethanimidic acid

Traditional Name

N(sup 4)-acetylsulfisomezole

CAS Registry Number

21312-10-7

SMILES

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

InChI Identifier

InChI=1S/C12H13N3O4S/c1-8-7-12(14-19-8)15-20(17,18)11-5-3-10(4-6-11)13-9(2)16/h3-7H,1-2H3,(H,13,16)(H,14,15)

InChI Key

GXPIUNZCALHVBA-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
Organosulfonic acid amide
Imidolactam
Azole
Isoxazole
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Heteroaromatic compound
Sulfonyl
Aminosulfonyl compound
Carboximidic acid
Carboximidic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organosulfur compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:31169 )
isoxazoles (CHEBI:31169 )

Ontology

Not Available

Liver (HMDB: HMDB0013854)
Kidney (HMDB: HMDB0013854)

Biofluid or Excreta

Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013854)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	0.86	Extrapolated

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	172.053	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001917
[M+H]+	Not Available	171.45	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001917

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	1.13	ALOGPS
logP	1.58	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	5.68	ChemAxon
pKa (Strongest Basic)	0.78	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	104.79 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.41 m³·mol⁻¹	ChemAxon
Polarizability	28.51 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]+	169.623	31661259
DarkChem	[M-H]-	168.341	31661259
DeepCCS	[M+H]+	172.121	30932474
DeepCCS	[M-H]-	169.762	30932474
DeepCCS	[M-2H]-	202.648	30932474
DeepCCS	[M+Na]+	178.214	30932474
AllCCS	[M+H]+	166.8	32859911
AllCCS	[M+H-H2O]+	163.4	32859911
AllCCS	[M+NH4]+	170.0	32859911
AllCCS	[M+Na]+	170.9	32859911
AllCCS	[M-H]-	164.8	32859911
AllCCS	[M+Na-2H]-	164.7	32859911
AllCCS	[M+HCOO]-	164.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N4-Acetylsulfamethoxazole	CC(O)=NC1=CC=C(C=C1)S(=O)(=O)NC1=NOC(C)=C1	3847.2	Standard polar	33892256
N4-Acetylsulfamethoxazole	CC(O)=NC1=CC=C(C=C1)S(=O)(=O)NC1=NOC(C)=C1	2735.0	Standard non polar	33892256
N4-Acetylsulfamethoxazole	CC(O)=NC1=CC=C(C=C1)S(=O)(=O)NC1=NOC(C)=C1	2577.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N4-Acetylsulfamethoxazole,1TMS,isomer #1	CC(=NC1=CC=C(S(=O)(=O)NC2=NOC(C)=C2)C=C1)O[Si](C)(C)C	2636.2	Semi standard non polar	33892256
N4-Acetylsulfamethoxazole,1TMS,isomer #2	CC(O)=NC1=CC=C(S(=O)(=O)N(C2=NOC(C)=C2)[Si](C)(C)C)C=C1	2628.4	Semi standard non polar	33892256
N4-Acetylsulfamethoxazole,2TMS,isomer #1	CC(=NC1=CC=C(S(=O)(=O)N(C2=NOC(C)=C2)[Si](C)(C)C)C=C1)O[Si](C)(C)C	2464.2	Semi standard non polar	33892256
N4-Acetylsulfamethoxazole,2TMS,isomer #1	CC(=NC1=CC=C(S(=O)(=O)N(C2=NOC(C)=C2)[Si](C)(C)C)C=C1)O[Si](C)(C)C	2634.9	Standard non polar	33892256
N4-Acetylsulfamethoxazole,2TMS,isomer #1	CC(=NC1=CC=C(S(=O)(=O)N(C2=NOC(C)=C2)[Si](C)(C)C)C=C1)O[Si](C)(C)C	3572.2	Standard polar	33892256
N4-Acetylsulfamethoxazole,1TBDMS,isomer #1	CC(=NC1=CC=C(S(=O)(=O)NC2=NOC(C)=C2)C=C1)O[Si](C)(C)C(C)(C)C	2919.9	Semi standard non polar	33892256
N4-Acetylsulfamethoxazole,1TBDMS,isomer #2	CC(O)=NC1=CC=C(S(=O)(=O)N(C2=NOC(C)=C2)[Si](C)(C)C(C)(C)C)C=C1	2881.9	Semi standard non polar	33892256
N4-Acetylsulfamethoxazole,2TBDMS,isomer #1	CC(=NC1=CC=C(S(=O)(=O)N(C2=NOC(C)=C2)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2963.1	Semi standard non polar	33892256
N4-Acetylsulfamethoxazole,2TBDMS,isomer #1	CC(=NC1=CC=C(S(=O)(=O)N(C2=NOC(C)=C2)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	3102.7	Standard non polar	33892256
N4-Acetylsulfamethoxazole,2TBDMS,isomer #1	CC(=NC1=CC=C(S(=O)(=O)N(C2=NOC(C)=C2)[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	3599.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N4-Acetylsulfamethoxazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6t-9360000000-1c2a094865717e2eadde	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N4-Acetylsulfamethoxazole GC-MS (1 TMS) - 70eV, Positive	splash10-0002-9231000000-4a60dfa1fba628eae89e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N4-Acetylsulfamethoxazole 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-QTOF , negative-QTOF	splash10-0007-0490000000-52c719984f40afb2fe69	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-QTOF , negative-QTOF	splash10-0002-0900000000-885f5298dc9cac736ad2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-QTOF , negative-QTOF	splash10-001i-0900000000-3845d94430e55b3672ce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-QTOF , negative-QTOF	splash10-001i-0900000000-0f28bd7306e116b23664	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-0002-0900000000-a931f6f79851f6517143	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-0006-0390000000-dba8d5adc6ad93ec8917	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-0002-0900000000-72a1ece66e1150c7e39e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-000t-0900000000-a95d8aa5899e8bda0fe6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-001i-0900000000-34815ffdbcd4883ad2dd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-001i-1900000000-1f10de1f050b43bd0fc4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-000x-6900000000-6d4e7909426bd265f9ca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-0006-0290000000-71d5ce544864c89f38cd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-0002-0900000000-43bf3d487b565393cd9e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-000t-0900000000-b0416b270d76be397989	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-001i-0900000000-25b614db8f59a5f5db39	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-001i-2900000000-626694102c1eea16e5a6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-0002-0900000000-7ce29f406bc6d908f6ea	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-0002-0900000000-5c819656360e2573a7d6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-0002-0900000000-59a88d63e4fe9a3c607f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole LC-ESI-ITFT , negative-QTOF	splash10-0002-0900000000-dafe8db52ffd9aba90db	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole 80V, Negative-QTOF	splash10-0002-0900000000-5c819656360e2573a7d6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole 30V, Negative-QTOF	splash10-0002-0900000000-72a1ece66e1150c7e39e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole 45V, Negative-QTOF	splash10-000t-0900000000-a95d8aa5899e8bda0fe6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole 55V, Negative-QTOF	splash10-0002-0900000000-7ce29f406bc6d908f6ea	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N4-Acetylsulfamethoxazole 35V, Negative-QTOF	splash10-0002-0900000000-59a88d63e4fe9a3c607f	2021-09-20	HMDB team, MONA	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58771

KEGG Compound ID

C13061

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

80641

PDB ID

Not Available

ChEBI ID

31169

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

Gobel A, McArdell CS, Suter MJ, Giger W: Trace determination of macrolide and sulfonamide antimicrobials, a human sulfonamide metabolite, and trimethoprim in wastewater using liquid chromatography coupled to electrospray tandem mass spectrometry. Anal Chem. 2004 Aug 15;76(16):4756-64. doi: 10.1021/ac0496603. [PubMed:15307787 ]
Asper R, Schmucki O: Critical aspects of urine and stone analysis. Appearance of iatrogenic urinary calculi. Urol Int. 1986;41(5):334-42. doi: 10.1159/000281233. [PubMed:3811034 ]
Weber A, Opheim KE, Siber GR, Ericson JF, Smith AL: High-performance liquid chromatographic quantitation of trimethoprim, sulfamethoxazole, and N4-acetylsulfamethoxazole in body fluids. J Chromatogr. 1983 Dec 9;278(2):337-45. doi: 10.1016/s0378-4347(00)84793-3. [PubMed:6668314 ]
Vree TB, Hekster YA, Baars AM, Damsma JE, Kleijin EV: Determination of trimethoprim and sulfamethoxazole (co-trimoxazole) in body fluids of man by means of high-performance liquid chromatography. J Chromatogr. 1978 Jul 1;146(1):103-12. doi: 10.1016/s0378-4347(00)81294-3. [PubMed:670346 ]

Showing metabocard for N4-Acetylsulfamethoxazole (HMDB0013854)

MOL for HMDB0013854 (N4-Acetylsulfamethoxazole)

3D MOL for HMDB0013854 (N4-Acetylsulfamethoxazole)

3D SDF for HMDB0013854 (N4-Acetylsulfamethoxazole)

3D-SDF for HMDB0013854 (N4-Acetylsulfamethoxazole)

PDB for HMDB0013854 (N4-Acetylsulfamethoxazole)

3D PDB for HMDB0013854 (N4-Acetylsulfamethoxazole)

SMILES for HMDB0013854 (N4-Acetylsulfamethoxazole)

INCHI for HMDB0013854 (N4-Acetylsulfamethoxazole)

Structure for HMDB0013854 (N4-Acetylsulfamethoxazole)

3D Structure for HMDB0013854 (N4-Acetylsulfamethoxazole)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra