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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:04 UTC

HMDB ID

HMDB0015688

Secondary Accession Numbers

HMDB15688

Metabolite Identification

Common Name

Sulfamoxole

Description

Sulfamoxole, also known as oxasulfa or sulphamoxolum, belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. Sulfamoxole is a drug which is used for the treatment of bacterial infection. Sulfamoxole is a moderately basic compound (based on its pKa). Sulfamoxole is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid. However, many strains of an individual species may be resistant.

Structure

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

HMDB0015688
     RDKit          3D
Sulfamoxole
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.5265    0.5149    1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2389   -0.0367    0.5470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7187   -1.2537    0.7576 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5585   -1.3333    0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6746   -2.4590    0.0371 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7886   -2.4127   -0.8711 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.4723   -3.7565   -0.7991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5176   -2.0745   -2.3167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918   -1.1578   -0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6398   -1.4350    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4191   -0.4137    1.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3870    0.8779    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2377    1.8498    1.3997 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5327    1.1335   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7337    0.1034   -0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3737   -0.1881   -0.5209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3590    0.6288   -0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4914    2.0213   -0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9745    1.2253    0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3983    0.9262    2.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2327   -0.3561    1.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8943   -3.3388    0.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254   -2.4154    1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0924   -0.6328    2.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2349    1.5943    1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9306    2.7900    1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4926    2.1309   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0910    0.4074   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8345    2.6369    0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2985    2.0739   -1.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5132    2.3493   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  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
  4 16  1  0
 16 17  1  0
 17 18  1  0
 17  2  2  0
 15  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 18 29  1  0
 18 30  1  0
 18 31  1  0
M  END

12894
  Mrv0541 02241214202D          

 18 19  0  0  0  0            999 V2000
    2.4751    0.2863    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    2.3443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.2863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.2863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    1.1113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9433    1.1883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -3.0138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -0.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0828    2.5158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4953    1.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -0.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -0.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -2.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4183    3.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3158    1.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  1  8  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  5  9  1  0  0  0  0
  6  9  2  0  0  0  0
  6 11  1  0  0  0  0
  7 16  1  0  0  0  0
  8 12  2  0  0  0  0
  8 13  1  0  0  0  0
 10 11  2  0  0  0  0
 10 17  1  0  0  0  0
 11 18  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015688

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C)N=C(NS(=O)(=O)C2=CC=C(N)C=C2)O1

> <INCHI_IDENTIFIER>
InChI=1S/C11H13N3O3S/c1-7-8(2)17-11(13-7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6H,12H2,1-2H3,(H,13,14)

> <INCHI_KEY>
CYFLXLSBHQBMFT-UHFFFAOYSA-N

> <FORMULA>
C11H13N3O3S

> <MOLECULAR_WEIGHT>
267.304

> <EXACT_MASS>
267.067761987

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.444221092556525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-N-(dimethyl-1,3-oxazol-2-yl)benzene-1-sulfonamide

> <ALOGPS_LOGP>
1.04

> <JCHEM_LOGP>
0.5890580276666666

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.808689436049524

> <JCHEM_PKA_STRONGEST_BASIC>
1.9356010208077885

> <JCHEM_POLAR_SURFACE_AREA>
98.22

> <JCHEM_REFRACTIVITY>
67.51450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfamoxole

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015688
     RDKit          3D
Sulfamoxole
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.5265    0.5149    1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2389   -0.0367    0.5470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7187   -1.2537    0.7576 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5585   -1.3333    0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6746   -2.4590    0.0371 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7886   -2.4127   -0.8711 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.4723   -3.7565   -0.7991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5176   -2.0745   -2.3167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918   -1.1578   -0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6398   -1.4350    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4191   -0.4137    1.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3870    0.8779    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2377    1.8498    1.3997 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5327    1.1335   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7337    0.1034   -0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3737   -0.1881   -0.5209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3590    0.6288   -0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4914    2.0213   -0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9745    1.2253    0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3983    0.9262    2.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2327   -0.3561    1.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8943   -3.3388    0.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254   -2.4154    1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0924   -0.6328    2.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2349    1.5943    1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9306    2.7900    1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4926    2.1309   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0910    0.4074   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8345    2.6369    0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2985    2.0739   -1.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5132    2.3493   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  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
  4 16  1  0
 16 17  1  0
 17 18  1  0
 17  2  2  0
 15  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 18 29  1  0
 18 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 12894                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  S   UNK     0       4.620   0.534   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       6.115   4.376   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.160   0.534   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080   0.534   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.620   2.074   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.361   2.218   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       4.620  -5.626   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.620  -1.006   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.954   2.844   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.621   4.696   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.391   3.362   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.286  -1.776   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.954  -1.776   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.286  -3.316   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.954  -3.316   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.620  -4.086   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.247   6.103   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.923   3.202   0.000  0.00  0.00           C+0
CONECT    1    3    4    5    8                                             
CONECT    2    9   10                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1    9                                                       
CONECT    6    9   11                                                       
CONECT    7   16                                                            
CONECT    8    1   12   13                                                  
CONECT    9    2    5    6                                                  
CONECT   10    2   11   17                                                  
CONECT   11    6   10   18                                                  
CONECT   12    8   14                                                       
CONECT   13    8   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   16                                                       
CONECT   16    7   14   15                                                  
CONECT   17   10                                                            
CONECT   18   11                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0015688
HETATM    1  C1  UNL     1       4.526   0.515   1.091  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.239  -0.037   0.547  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.719  -1.254   0.758  1.00  0.00           N  
HETATM    4  C3  UNL     1       1.559  -1.333   0.087  1.00  0.00           C  
HETATM    5  N2  UNL     1       0.675  -2.459   0.037  1.00  0.00           N  
HETATM    6  S1  UNL     1      -0.789  -2.413  -0.871  1.00  0.00           S  
HETATM    7  O1  UNL     1      -1.472  -3.757  -0.799  1.00  0.00           O  
HETATM    8  O2  UNL     1      -0.518  -2.075  -2.317  1.00  0.00           O  
HETATM    9  C4  UNL     1      -1.792  -1.158  -0.211  1.00  0.00           C  
HETATM   10  C5  UNL     1      -2.640  -1.435   0.823  1.00  0.00           C  
HETATM   11  C6  UNL     1      -3.419  -0.414   1.314  1.00  0.00           C  
HETATM   12  C7  UNL     1      -3.387   0.878   0.813  1.00  0.00           C  
HETATM   13  N3  UNL     1      -4.238   1.850   1.400  1.00  0.00           N  
HETATM   14  C8  UNL     1      -2.533   1.134  -0.221  1.00  0.00           C  
HETATM   15  C9  UNL     1      -1.734   0.103  -0.730  1.00  0.00           C  
HETATM   16  O3  UNL     1       1.374  -0.188  -0.521  1.00  0.00           O  
HETATM   17  C10 UNL     1       2.359   0.629  -0.276  1.00  0.00           C  
HETATM   18  C11 UNL     1       2.491   2.021  -0.798  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.974   1.225   0.383  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.398   0.926   2.109  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.233  -0.356   1.145  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.894  -3.339   0.551  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.725  -2.415   1.272  1.00  0.00           H  
HETATM   24  H6  UNL     1      -4.092  -0.633   2.135  1.00  0.00           H  
HETATM   25  H7  UNL     1      -5.235   1.594   1.550  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.931   2.790   1.686  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.493   2.131  -0.625  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.091   0.407  -1.552  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.834   2.637   0.066  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.298   2.074  -1.561  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.513   2.349  -1.187  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   17   17
CONECT    3    4    4
CONECT    4    5   16
CONECT    5    6   22
CONECT    6    7    7    8    8
CONECT    6    9
CONECT    9   10   10   15
CONECT   10   11   23
CONECT   11   12   12   24
CONECT   12   13   14
CONECT   13   25   26
CONECT   14   15   15   27
CONECT   15   28
CONECT   16   17
CONECT   17   18
CONECT   18   29   30   31
END

HMDB0015688
     RDKit          3D
Sulfamoxole
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.5265    0.5149    1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2389   -0.0367    0.5470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7187   -1.2537    0.7576 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5585   -1.3333    0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6746   -2.4590    0.0371 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7886   -2.4127   -0.8711 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.4723   -3.7565   -0.7991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5176   -2.0745   -2.3167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918   -1.1578   -0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6398   -1.4350    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4191   -0.4137    1.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3870    0.8779    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2377    1.8498    1.3997 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5327    1.1335   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7337    0.1034   -0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3737   -0.1881   -0.5209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3590    0.6288   -0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4914    2.0213   -0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9745    1.2253    0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3983    0.9262    2.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2327   -0.3561    1.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8943   -3.3388    0.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254   -2.4154    1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0924   -0.6328    2.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2349    1.5943    1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9306    2.7900    1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4926    2.1309   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0910    0.4074   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8345    2.6369    0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2985    2.0739   -1.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5132    2.3493   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  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
  4 16  1  0
 16 17  1  0
 17 18  1  0
 17  2  2  0
 15  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 18 29  1  0
 18 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(p-Aminobenzenesulfonamido)-4,5-dimethyloxazole	ChEBI
2-(p-Aminobenzolsulfonamido)-4,5-dimethyloxazol	ChEBI
4,5-Dimethyl-2-sulfanilamidooxazole	ChEBI
4-Amino-N-(4,5-dimethyl-2-oxazolyl)benzenesulfonamide	ChEBI
N1-(4,5-Dimethyl-2-oxazolyl)sulfanilamide	ChEBI
Oxasulfa	ChEBI
p-Aminobenzenesulfonyl-2-amino-4,5-dimethyloxazole	ChEBI
Sulfadimethyloxazole	ChEBI
Sulfamoxol	ChEBI
Sulfamoxolum	ChEBI
Sulphamoxole	ChEBI
2-(p-Aminobenzenesulphonamido)-4,5-dimethyloxazole	Generator
2-(p-Aminobenzolsulphonamido)-4,5-dimethyloxazol	Generator
4,5-Dimethyl-2-sulphanilamidooxazole	Generator
4-Amino-N-(4,5-dimethyl-2-oxazolyl)benzenesulphonamide	Generator
N1-(4,5-Dimethyl-2-oxazolyl)sulphanilamide	Generator
Oxasulpha	Generator
p-Aminobenzenesulphonyl-2-amino-4,5-dimethyloxazole	Generator
Sulphadimethyloxazole	Generator
Sulphamoxol	Generator
Sulphamoxolum	Generator
Sulfono	HMDB

Chemical Formula

C₁₁H₁₃N₃O₃S

Average Molecular Weight

267.304

Monoisotopic Molecular Weight

267.067761987

IUPAC Name

4-amino-N-(dimethyl-1,3-oxazol-2-yl)benzene-1-sulfonamide

Traditional Name

sulfamoxole

CAS Registry Number

729-99-7

SMILES

CC1=C(C)N=C(NS(=O)(=O)C2=CC=C(N)C=C2)O1

InChI Identifier

InChI=1S/C11H13N3O3S/c1-7-8(2)17-11(13-7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6H,12H2,1-2H3,(H,13,14)

InChI Key

CYFLXLSBHQBMFT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Aminobenzenesulfonamides

Alternative Parents

Substituents

Aminobenzenesulfonamide
Benzenesulfonyl group
2,4,5-trisubstituted 1,3-oxazole
Aniline or substituted anilines
Organosulfonic acid amide
Azole
Oxazole
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Heteroaromatic compound
Organoheterocyclic compound
Azacycle
Oxacycle
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Primary amine
Amine
Organosulfur compound
Organonitrogen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:55548 )
sulfonamide antibiotic (CHEBI:55548 )
oxazole (CHEBI:55548 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015688)

Source

Exogenous

Exogenous (HMDB: HMDB0015688)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	185 °C	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	0.27 g/L	ALOGPS
logP	1.04	ALOGPS
logP	0.59	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.81	ChemAxon
pKa (Strongest Basic)	1.94	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	98.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.51 m³·mol⁻¹	ChemAxon
Polarizability	27.44 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]+	162.429	31661259
DarkChem	[M-H]-	164.544	31661259
DeepCCS	[M+H]+	160.985	30932474
DeepCCS	[M-H]-	158.627	30932474
DeepCCS	[M-2H]-	192.102	30932474
DeepCCS	[M+Na]+	167.281	30932474
AllCCS	[M+H]+	160.6	32859911
AllCCS	[M+H-H2O]+	156.9	32859911
AllCCS	[M+NH4]+	164.0	32859911
AllCCS	[M+Na]+	165.0	32859911
AllCCS	[M-H]-	158.3	32859911
AllCCS	[M+Na-2H]-	158.4	32859911
AllCCS	[M+HCOO]-	158.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sulfamoxole	CC1=C(C)N=C(NS(=O)(=O)C2=CC=C(N)C=C2)O1	4095.1	Standard polar	33892256
Sulfamoxole	CC1=C(C)N=C(NS(=O)(=O)C2=CC=C(N)C=C2)O1	2486.7	Standard non polar	33892256
Sulfamoxole	CC1=C(C)N=C(NS(=O)(=O)C2=CC=C(N)C=C2)O1	2522.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sulfamoxole,1TMS,isomer #1	CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N1	2827.1	Semi standard non polar	33892256
Sulfamoxole,1TMS,isomer #1	CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N1	2516.8	Standard non polar	33892256
Sulfamoxole,1TMS,isomer #1	CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N1	3536.6	Standard polar	33892256
Sulfamoxole,1TMS,isomer #2	CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N1	2564.4	Semi standard non polar	33892256
Sulfamoxole,1TMS,isomer #2	CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N1	2437.0	Standard non polar	33892256
Sulfamoxole,1TMS,isomer #2	CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N1	3740.0	Standard polar	33892256
Sulfamoxole,2TMS,isomer #1	CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N1	2610.5	Semi standard non polar	33892256
Sulfamoxole,2TMS,isomer #1	CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N1	2572.8	Standard non polar	33892256
Sulfamoxole,2TMS,isomer #1	CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N1	3208.9	Standard polar	33892256
Sulfamoxole,2TMS,isomer #2	CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N1	2685.1	Semi standard non polar	33892256
Sulfamoxole,2TMS,isomer #2	CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N1	2613.4	Standard non polar	33892256
Sulfamoxole,2TMS,isomer #2	CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N1	3285.5	Standard polar	33892256
Sulfamoxole,3TMS,isomer #1	CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N1	2540.3	Semi standard non polar	33892256
Sulfamoxole,3TMS,isomer #1	CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N1	2708.0	Standard non polar	33892256
Sulfamoxole,3TMS,isomer #1	CC1=C(C)OC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N1	3049.4	Standard polar	33892256
Sulfamoxole,1TBDMS,isomer #1	CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N1	3060.3	Semi standard non polar	33892256
Sulfamoxole,1TBDMS,isomer #1	CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N1	2732.9	Standard non polar	33892256
Sulfamoxole,1TBDMS,isomer #1	CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N1	3545.6	Standard polar	33892256
Sulfamoxole,1TBDMS,isomer #2	CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N1	2813.6	Semi standard non polar	33892256
Sulfamoxole,1TBDMS,isomer #2	CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N1	2659.2	Standard non polar	33892256
Sulfamoxole,1TBDMS,isomer #2	CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N1	3704.8	Standard polar	33892256
Sulfamoxole,2TBDMS,isomer #1	CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N1	3095.5	Semi standard non polar	33892256
Sulfamoxole,2TBDMS,isomer #1	CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N1	3036.9	Standard non polar	33892256
Sulfamoxole,2TBDMS,isomer #1	CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N1	3295.8	Standard polar	33892256
Sulfamoxole,2TBDMS,isomer #2	CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N1	3175.9	Semi standard non polar	33892256
Sulfamoxole,2TBDMS,isomer #2	CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N1	3039.0	Standard non polar	33892256
Sulfamoxole,2TBDMS,isomer #2	CC1=C(C)OC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N1	3321.3	Standard polar	33892256
Sulfamoxole,3TBDMS,isomer #1	CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N1	3243.4	Semi standard non polar	33892256
Sulfamoxole,3TBDMS,isomer #1	CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N1	3408.5	Standard non polar	33892256
Sulfamoxole,3TBDMS,isomer #1	CC1=C(C)OC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N1	3222.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfamoxole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0903-9520000000-b17afcbf8fbe531fe5f3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfamoxole 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 - Sulfamoxole LC-ESI-QTOF , positive-QTOF	splash10-0a4i-3900000000-23eed4bc89bcf24079bd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 15V, Positive-QTOF	splash10-066r-0960000000-5324e421d0898ec1099e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 75V, Positive-QTOF	splash10-07bf-9500000000-9e755c5d161870e20cc1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 30V, Positive-QTOF	splash10-0bt9-4900000000-f0d6577fe251f478a2b3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 25V, Positive-QTOF	splash10-05mo-9600000000-656e8ab90054a33c8a96	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 80V, Positive-QTOF	splash10-066u-9400000000-4d435cd7a788a59f537f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 45V, Positive-QTOF	splash10-014i-9100000000-8c8c9b24422573071135	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 30V, Positive-QTOF	splash10-05mo-9300000000-6e87579d1c4dcc3385d3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 45V, Positive-QTOF	splash10-066u-9400000000-328720644b3d39690ea8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 50V, Positive-QTOF	splash10-014i-9000000000-70248a5e493d759c8908	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 75V, Positive-QTOF	splash10-014i-9000000000-2d46e7d146924e2cc1ca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 60V, Positive-QTOF	splash10-014i-9100000000-b69806557c6ee27e2cf5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 35V, Positive-QTOF	splash10-014l-9200000000-8def04b9696db2663618	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 30V, Positive-QTOF	splash10-0a4i-0900000000-b95f9545732c76bf65ef	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 15V, Positive-QTOF	splash10-0btc-6900000000-747f05ef6971ea73b013	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 30V, Positive-QTOF	splash10-0bt9-4900000000-78c0ee8433765de7a021	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 20V, Positive-QTOF	splash10-0btc-9800000000-21eddbd29f724651aeea	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 25V, Positive-QTOF	splash10-0a4i-0910000000-66e1d1317255c54345a9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamoxole 35V, Positive-QTOF	splash10-0a4i-1900000000-c35120697abf544edf88	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamoxole 10V, Positive-QTOF	splash10-0gi0-0590000000-b63b59b327f5e5fee30d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamoxole 20V, Positive-QTOF	splash10-00di-2920000000-e352f9ce158638c8d63a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamoxole 40V, Positive-QTOF	splash10-0ftf-9110000000-06f8a9a3d0a07b30754f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamoxole 10V, Negative-QTOF	splash10-014i-0190000000-4d3645049982bea395a3	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamoxole 20V, Negative-QTOF	splash10-00di-2930000000-178776a8f92cbb18ce74	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamoxole 40V, Negative-QTOF	splash10-002f-9400000000-aa4062cd0b19cdf35d94	2016-08-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB08798	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08798	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08798

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

12361

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulfamoxole

METLIN ID

Not Available

PubChem Compound

12894

PDB ID

Not Available

ChEBI ID

55548

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

DUGGER JA: Sulfamoxole (Nuprin), a new sulfonamide, in pediatric practice. J New Drugs. 1961 Sep-Oct;1:223-9. [PubMed:13888264 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2C9

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

References

Zweers-Zeilmaker WM, Horbach GJ, Witkamp RF: Differential inhibitory effects of phenytoin, diclofenac, phenylbutazone and a series of sulfonamides on hepatic cytochrome P4502C activity in vitro, and correlation with some molecular descriptors in the dwarf goat (Caprus hircus aegagrus). Xenobiotica. 1997 Aug;27(8):769-80. [PubMed:9293615 ]

Showing metabocard for Sulfamoxole (HMDB0015688)

MOL for HMDB0015688 (Sulfamoxole)

3D MOL for HMDB0015688 (Sulfamoxole)

3D SDF for HMDB0015688 (Sulfamoxole)

3D-SDF for HMDB0015688 (Sulfamoxole)

PDB for HMDB0015688 (Sulfamoxole)

3D PDB for HMDB0015688 (Sulfamoxole)

SMILES for HMDB0015688 (Sulfamoxole)

INCHI for HMDB0015688 (Sulfamoxole)

Structure for HMDB0015688 (Sulfamoxole)

3D Structure for HMDB0015688 (Sulfamoxole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References