Hmdb loader

Showing metabocard for Sulfamethoxazole (HMDB0015150)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:53 UTC
HMDB IDHMDB0015150
Secondary Accession Numbers
  • HMDB15150
Metabolite Identification
Common NameSulfamethoxazole
DescriptionSulfamethoxazole is only found in individuals that have used or taken this drug. It is a bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208)Sulfonamides inhibit the enzymatic conversion of pteridine and p-aminobenzoic acid (PABA) to dihydropteroic acid by competing with PABA for binding to dihydrofolate synthetase, an intermediate of tetrahydrofolic acid (THF) synthesis. THF is required for the synthesis of purines and dTMP and inhibition of its synthesis inhibits bacterial growth. Pyrimethamine and trimethoprim inhibit dihydrofolate reductase, another step in THF synthesis, and therefore act synergistically with the sulfonamides.
Structure
Data?1582753264
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015150 (Sulfamethoxazole)

1015
  Mrv0541 02231215102D          

 17 18  0  0  0  0            999 V2000
    2.4751    0.6631    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0828    2.8927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    1.4882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    2.7212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -2.6369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -0.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -0.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -0.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9433    1.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4953    2.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3158    2.0920    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  6  1  0  0  0  0
  2 16  1  0  0  0  0
  5 11  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 14  2  0  0  0  0
 11 15  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
Download

3D MOL for HMDB0015150 (Sulfamethoxazole)

HMDB0015150
     RDKit          3D
Sulfamethoxazole
 28 29  0  0  0  0  0  0  0  0999 V2000
   -3.6276   -1.0709    1.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2677    0.1150    0.9698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2599    0.0644   -0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1596    1.3111   -0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148    1.7759   -1.6104 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.7930   -2.3659 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.5261    1.5725   -3.4736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773   -0.3779   -2.9959 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0998    0.2227   -1.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1177   -1.0454   -0.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980   -1.4711    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1271   -0.6222    0.4967 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1436   -1.0589    1.3914 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1091    0.6525   -0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1315    1.0786   -0.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1137    2.0509    0.0790 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7159    1.3178    0.9524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3454   -2.0149    1.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2514   -1.0162    2.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7560   -1.0758    1.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6693   -0.7831   -0.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4600    2.7844   -1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3441   -1.7601   -1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1254   -2.4716    0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5761   -0.3226    1.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4556   -2.0457    1.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9338    1.3101    0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1649    2.0873   -1.2751 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
 12 14  1  0
 14 15  2  0
  4 16  2  0
 16 17  1  0
 17  2  1  0
 15  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 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
M  END
Download

3D SDF for HMDB0015150 (Sulfamethoxazole)

1015
  Mrv0541 02231215102D          

 17 18  0  0  0  0            999 V2000
    2.4751    0.6631    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0828    2.8927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    1.4882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    2.7212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -2.6369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -0.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -0.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -0.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9433    1.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4953    2.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3158    2.0920    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  6  1  0  0  0  0
  2 16  1  0  0  0  0
  5 11  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 14  2  0  0  0  0
 11 15  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015150

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1

> <INCHI_IDENTIFIER>
InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)

> <INCHI_KEY>
JLKIGFTWXXRPMT-UHFFFAOYSA-N

> <FORMULA>
C10H11N3O3S

> <MOLECULAR_WEIGHT>
253.278

> <EXACT_MASS>
253.052111923

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
24.986434544882528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.79

> <JCHEM_LOGP>
0.7905493986666665

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.160732172136757

> <JCHEM_PKA_STRONGEST_BASIC>
1.9717778683222775

> <JCHEM_POLAR_SURFACE_AREA>
98.22

> <JCHEM_REFRACTIVITY>
64.4958

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfamethoxazole

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0015150 (Sulfamethoxazole)

HMDB0015150
     RDKit          3D
Sulfamethoxazole
 28 29  0  0  0  0  0  0  0  0999 V2000
   -3.6276   -1.0709    1.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2677    0.1150    0.9698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2599    0.0644   -0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1596    1.3111   -0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148    1.7759   -1.6104 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.7930   -2.3659 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.5261    1.5725   -3.4736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773   -0.3779   -2.9959 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0998    0.2227   -1.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1177   -1.0454   -0.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980   -1.4711    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1271   -0.6222    0.4967 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1436   -1.0589    1.3914 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1091    0.6525   -0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1315    1.0786   -0.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1137    2.0509    0.0790 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7159    1.3178    0.9524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3454   -2.0149    1.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2514   -1.0162    2.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7560   -1.0758    1.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6693   -0.7831   -0.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4600    2.7844   -1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3441   -1.7601   -1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1254   -2.4716    0.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5761   -0.3226    1.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4556   -2.0457    1.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9338    1.3101    0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1649    2.0873   -1.2751 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
 12 14  1  0
 14 15  2  0
  4 16  2  0
 16 17  1  0
 17  2  1  0
 15  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 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
M  END
Download

PDB for HMDB0015150 (Sulfamethoxazole)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1015                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.620   1.238   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       7.621   5.400   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.080   1.238   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.160   1.238   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.620   2.778   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       6.115   5.080   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       4.620  -4.922   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.620  -0.302   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.286  -1.072   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.954  -1.072   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.954   3.548   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.620  -3.382   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.286  -2.612   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.954  -2.612   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.361   2.922   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.391   4.066   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.923   3.905   0.000  0.00  0.00           C+0
CONECT    1    3    4    5    8                                             
CONECT    2    6   16                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1   11                                                       
CONECT    6    2   11                                                       
CONECT    7   12                                                            
CONECT    8    1    9   10                                                  
CONECT    9    8   13                                                       
CONECT   10    8   14                                                       
CONECT   11    5    6   15                                                  
CONECT   12    7   13   14                                                  
CONECT   13    9   12                                                       
CONECT   14   10   12                                                       
CONECT   15   11   16                                                       
CONECT   16    2   15   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END
Download

3D PDB for HMDB0015150 (Sulfamethoxazole)

COMPND    HMDB0015150
HETATM    1  C1  UNL     1      -3.628  -1.071   1.777  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.268   0.115   0.970  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.260   0.064  -0.004  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.160   1.311  -0.579  1.00  0.00           C  
HETATM    5  N1  UNL     1      -1.315   1.776  -1.610  1.00  0.00           N  
HETATM    6  S1  UNL     1      -0.134   0.793  -2.366  1.00  0.00           S  
HETATM    7  O1  UNL     1       0.526   1.572  -3.474  1.00  0.00           O  
HETATM    8  O2  UNL     1      -0.877  -0.378  -2.996  1.00  0.00           O  
HETATM    9  C5  UNL     1       1.100   0.223  -1.277  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.118  -1.045  -0.753  1.00  0.00           C  
HETATM   11  C7  UNL     1       2.098  -1.471   0.111  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.127  -0.622   0.497  1.00  0.00           C  
HETATM   13  N2  UNL     1       4.144  -1.059   1.391  1.00  0.00           N  
HETATM   14  C9  UNL     1       3.109   0.653  -0.030  1.00  0.00           C  
HETATM   15  C10 UNL     1       2.132   1.079  -0.892  1.00  0.00           C  
HETATM   16  N3  UNL     1      -3.114   2.051   0.079  1.00  0.00           N  
HETATM   17  O3  UNL     1      -3.716   1.318   0.952  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.345  -2.015   1.267  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.251  -1.016   2.821  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.756  -1.076   1.828  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.669  -0.783  -0.272  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.460   2.784  -1.891  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.344  -1.760  -1.022  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.125  -2.472   0.534  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.576  -0.323   1.996  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.456  -2.046   1.459  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.934   1.310   0.288  1.00  0.00           H  
HETATM   28  H11 UNL     1       2.165   2.087  -1.275  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   17
CONECT    3    4   21
CONECT    4    5   16   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
END
Download

SMILES for HMDB0015150 (Sulfamethoxazole)

CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1
Download

INCHI for HMDB0015150 (Sulfamethoxazole)

InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
3-(p-Aminophenylsulfonamido)-5-methylisoxazoleChEBI
3-Sulfanilamido-5-methylisoxazoleChEBI
4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamideChEBI
GantanolChEBI
SMXChEBI
SulphamethoxazoleChEBI
3-(p-Aminophenylsulphonamido)-5-methylisoxazoleGenerator
3-Sulphanilamido-5-methylisoxazoleGenerator
4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulphonamideGenerator
3-(p-Aminobenzenesulfonamido)-5-methylisoxazoleHMDB
3-(Para-aminophenylsulphonamido)-5-methylisoxazoleHMDB
4-Amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamideHMDB
4-Amino-N-(5-methyl-3-isoxazolyl)-benzenesulfonamideHMDB
5-Methyl-3-sulfanilamidoisoxazoleHMDB
5-Methyl-3-sulfanylamidoisoxazoleHMDB
5-Methyl-3-sulfonylamidoisoxazoleHMDB
5-Methyl-3-sulphanil-amidoisoxazoleHMDB
Azo-gantanolHMDB
BactrimHMDB
MetoxalHMDB
N'-(5-methyl-3-isoxazole)sulfanilamideHMDB
N'-(5-methyl-3-isoxazolyl)-sulfanilamideHMDB
N'-(5-methyl-3-isoxazolyl)sulfanilamideHMDB
N'-(5-methylisoxazol-3-yl)sulphanilamideHMDB
N1-(5-Methyl-3-isoxazolyl)-sulfanilamideHMDB
N1-(5-Methyl-3-isoxazolyl)sulfanilamideHMDB
N1-(5-Methyl-3-isoxazolyl)sulphanilamideHMDB
Ndimethyl1-(5-methyl-3-isoxazolyl)-sulfanilamideHMDB
N^1-(5-methyl-3-isoxazolyl)-sulfanilamideHMDB
RadonilHMDB
SimsinominHMDB
SinominHMDB
SulfamethalazoleHMDB
SulfamethoxazolHMDB
Sulfamethoxazole(usan)HMDB
SulfamethylisoxazoleHMDB
SulfisomezoleHMDB
Sulpha-methoxizoleHMDB
SulphamethoxazolHMDB
SulphamethylisoxazoleHMDB
SulphisomezoleHMDB
Chemical FormulaC10H11N3O3S
Average Molecular Weight253.278
Monoisotopic Molecular Weight253.052111923
IUPAC Name4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide
Traditional Namesulfamethoxazole
CAS Registry Number723-46-6
SMILES
CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1
InChI Identifier
InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
InChI KeyJLKIGFTWXXRPMT-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Benzenesulfonyl group
  • Aniline or substituted anilines
  • Organosulfonic acid amide
  • Imidolactam
  • Azole
  • Isoxazole
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Primary amine
  • Organosulfur compound
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point167 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.46 g/LNot Available
LogP0.7Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM151.030932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.46 g/LALOGPS
logP0.79ALOGPS
logP0.79ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)6.16ChemAxon
pKa (Strongest Basic)1.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area98.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.5 m³·mol⁻¹ChemAxon
Polarizability24.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+158.39331661259
DarkChem[M-H]-160.17231661259
DeepCCS[M+H]+155.34630932474
DeepCCS[M-H]-152.98830932474
DeepCCS[M-2H]-186.10530932474
DeepCCS[M+Na]+161.43930932474
AllCCS[M+H]+157.332859911
AllCCS[M+H-H2O]+153.532859911
AllCCS[M+NH4]+160.932859911
AllCCS[M+Na]+161.932859911
AllCCS[M-H]-153.832859911
AllCCS[M+Na-2H]-153.932859911
AllCCS[M+HCOO]-154.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SulfamethoxazoleCC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO13996.1Standard polar33892256
SulfamethoxazoleCC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO12421.0Standard non polar33892256
SulfamethoxazoleCC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO12439.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sulfamethoxazole,1TMS,isomer #1CC1=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NO12766.8Semi standard non polar33892256
Sulfamethoxazole,1TMS,isomer #1CC1=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NO12458.9Standard non polar33892256
Sulfamethoxazole,1TMS,isomer #1CC1=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NO13692.4Standard polar33892256
Sulfamethoxazole,1TMS,isomer #2CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NO12525.7Semi standard non polar33892256
Sulfamethoxazole,1TMS,isomer #2CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NO12388.9Standard non polar33892256
Sulfamethoxazole,1TMS,isomer #2CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NO13756.4Standard polar33892256
Sulfamethoxazole,2TMS,isomer #1CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NO12527.6Semi standard non polar33892256
Sulfamethoxazole,2TMS,isomer #1CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NO12518.2Standard non polar33892256
Sulfamethoxazole,2TMS,isomer #1CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NO13216.3Standard polar33892256
Sulfamethoxazole,2TMS,isomer #2CC1=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NO12607.3Semi standard non polar33892256
Sulfamethoxazole,2TMS,isomer #2CC1=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NO12559.8Standard non polar33892256
Sulfamethoxazole,2TMS,isomer #2CC1=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NO13433.5Standard polar33892256
Sulfamethoxazole,3TMS,isomer #1CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NO12429.2Semi standard non polar33892256
Sulfamethoxazole,3TMS,isomer #1CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NO12626.7Standard non polar33892256
Sulfamethoxazole,3TMS,isomer #1CC1=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NO13052.9Standard polar33892256
Sulfamethoxazole,1TBDMS,isomer #1CC1=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NO13017.1Semi standard non polar33892256
Sulfamethoxazole,1TBDMS,isomer #1CC1=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NO12681.2Standard non polar33892256
Sulfamethoxazole,1TBDMS,isomer #1CC1=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NO13691.1Standard polar33892256
Sulfamethoxazole,1TBDMS,isomer #2CC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NO12788.8Semi standard non polar33892256
Sulfamethoxazole,1TBDMS,isomer #2CC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NO12614.9Standard non polar33892256
Sulfamethoxazole,1TBDMS,isomer #2CC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NO13727.7Standard polar33892256
Sulfamethoxazole,2TBDMS,isomer #1CC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NO13035.9Semi standard non polar33892256
Sulfamethoxazole,2TBDMS,isomer #1CC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NO12964.6Standard non polar33892256
Sulfamethoxazole,2TBDMS,isomer #1CC1=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NO13300.4Standard polar33892256
Sulfamethoxazole,2TBDMS,isomer #2CC1=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NO13133.7Semi standard non polar33892256
Sulfamethoxazole,2TBDMS,isomer #2CC1=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NO12992.5Standard non polar33892256
Sulfamethoxazole,2TBDMS,isomer #2CC1=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NO13429.6Standard polar33892256
Sulfamethoxazole,3TBDMS,isomer #1CC1=CC(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)=NO13174.4Semi standard non polar33892256
Sulfamethoxazole,3TBDMS,isomer #1CC1=CC(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)=NO13281.0Standard non polar33892256
Sulfamethoxazole,3TBDMS,isomer #1CC1=CC(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)=NO13223.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Sulfamethoxazole EI-B (Non-derivatized)splash10-05mo-8900000000-8a6ba1e89f89f5cb1e3c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sulfamethoxazole EI-B (Non-derivatized)splash10-05mo-8900000000-8a6ba1e89f89f5cb1e3c2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfamethoxazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9120000000-73aebd463dbf4176fb012017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfamethoxazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-QTOF , negative-QTOFsplash10-0a4i-0940000000-88c5b1ef2f503737ca9a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-QTOF , negative-QTOFsplash10-0a4i-0900000000-b1b1b8e70ec8043bb89b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-QTOF , negative-QTOFsplash10-0a4i-0900000000-f9d7f50685c7e96eefcd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0900000000-465bcb56920d86311f932017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0udi-0390000000-5dac2c73d05262cd10c02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0900000000-754d521e9fa8d49057e72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0900000000-5dea192ddf68e39f5c6c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0a4i-5900000000-f376319dc72913e8db612017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-08fu-9300000000-275ed92901e4719e8eb02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0udi-0290000000-b02c397c2d2954785c812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0900000000-c61eade368561111e9082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0900000000-c85d502fd299d3c8942c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0a4i-4900000000-c8c24b18f27b59f6e6932017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0900000000-c61eade368561111e9082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-QTOF , negative-QTOFsplash10-0a4i-0910000000-64449078c4fdd8bf46142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-QTOF , negative-QTOFsplash10-0a4i-3900000000-58869a5ce23e7feeeedf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole LC-ESI-QTOF , negative-QTOFsplash10-03di-9000000000-c388b00730b45caa46482017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole 15V, Negative-QTOFsplash10-0udi-0390000000-5dac2c73d05262cd10c02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole 45V, Negative-QTOFsplash10-0a4i-0900000000-c85d502fd299d3c8942c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole 60V, Negative-QTOFsplash10-0a4i-4900000000-c8c24b18f27b59f6e6932021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole 30V, Negative-QTOFsplash10-0a4i-0900000000-754d521e9fa8d49057e72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole 35V, Negative-QTOFsplash10-0a4i-0900000000-edae1e1e2ba8943cd0ea2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole 30V, Negative-QTOFsplash10-0a4i-0900000000-c61eade368561111e9082021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole 30V, Negative-QTOFsplash10-0a4i-0900000000-f9d7f50685c7e96eefcd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethoxazole 15V, Negative-QTOFsplash10-0udi-0290000000-b02c397c2d2954785c812021-09-20HMDB team, MONAView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01015 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01015 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01015
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5138
KEGG Compound IDC07315
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfamethoxazole
METLIN IDNot Available
PubChem Compound5329
PDB ID08D
ChEBI ID9332
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hobday JD: The prophylactic treatment of recurrent urinary tract infection with sulphamethoxizole-trimethoprim. Aust Paediatr J. 1971 Dec;7(4):199-202. [PubMed:5140758 ]
  2. Arora VK, Tumbanatham A, Kumar SV, Ratnakar C: Pneumocystis carinii pneumonia simulating as pulmonary tuberculosis in AIDS. Indian J Chest Dis Allied Sci. 1996 Oct-Dec;38(4):253-7. [PubMed:9018980 ]