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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 02:51:58 UTC

HMDB ID

HMDB0015413

Secondary Accession Numbers

HMDB15413

Metabolite Identification

Common Name

Sulfadoxine

Description

Sulfadoxine is only found in individuals that have used or taken this drug. It is a long acting sulfonamide that is used, usually in combination with other drugs, for respiratory, urinary tract, and malarial infections. [PubChem]Sulfadoxine is a sulfa drug, often used in combination with pyrimethamine to treat malaria. This medicine may also be used to prevent malaria in people who are living in, or will be traveling to, an area where there is a chance of getting malaria. Sulfadoxine targets Plasmodium dihydropteroate synthase and dihydrofolate reductase. Sulfa drugs or Sulfonamides are antimetabolites. They compete with para-aminobenzoic acid (PABA) for incorporation into folic acid. The action of sulfonamides exploits the difference between mammal cells and other kinds of cells in their folic acid metabolism. All cells require folic acid for growth. Folic acid (as a vitamin) diffuses or is transported into human cells. However, folic acid cannot cross bacterial (and certain protozoan) cell walls by diffusion or active transport. For this reason bacteria must synthesize folic acid from p-aminobenzoic acid.

Structure

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

HMDB0015413
     RDKit          3D
Sulfadoxine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.7768    2.2155   -0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9520    1.6850    0.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8718    0.8535   -0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6151    0.5506   -1.4141 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5807   -0.2494   -1.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -0.7202   -0.7068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -0.4515    0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   -0.9930    1.5964 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0953   -2.0043    1.1548 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.5573   -3.1979    0.3773 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -2.5519    2.3601 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -1.2448    0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2652   -1.3131   -1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -0.7095   -2.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2287    0.0093   -1.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1897    0.6274   -2.2812 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2841    0.1013   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3360   -0.5102    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211    0.3814    0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3715    0.6826    2.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2107   -0.0704    3.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4163    1.9045   -1.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8029    1.8311   -0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7632    3.3208   -0.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747   -0.4942   -2.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3862   -0.7741    2.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4823   -1.8685   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1762   -0.7707   -3.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5727    0.1916   -3.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721    1.5855   -2.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0954    0.6686    0.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -0.4173    1.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0840   -1.1499    2.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8817    0.1274    4.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2642    0.2151    3.0107 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  7 19  2  0
 19 20  1  0
 20 21  1  0
 19  3  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
 21 34  1  0
 21 35  1  0
M  END

1299
  Mrv0541 02231215222D          

 21 22  0  0  0  0            999 V2000
    4.5080    0.7755    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205    0.0611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955    1.4900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.1120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.3630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.4256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.1120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  6  1  0  0  0  0
  1 10  1  0  0  0  0
  4 14  1  0  0  0  0
  4 20  1  0  0  0  0
  5 18  1  0  0  0  0
  5 21  1  0  0  0  0
  6 11  1  0  0  0  0
  7 11  1  0  0  0  0
  7 19  2  0  0  0  0
  8 17  1  0  0  0  0
  9 18  2  0  0  0  0
  9 19  1  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 14 18  1  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015413

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=NC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)

> <INCHI_KEY>
PJSFRIWCGOHTNF-UHFFFAOYSA-N

> <FORMULA>
C12H14N4O4S

> <MOLECULAR_WEIGHT>
310.329

> <EXACT_MASS>
310.073575646

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
30.008576424631322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide

> <ALOGPS_LOGP>
0.72

> <JCHEM_LOGP>
0.5820473146666669

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.116187571361608

> <JCHEM_PKA_STRONGEST_BASIC>
2.553081197758056

> <JCHEM_POLAR_SURFACE_AREA>
116.43

> <JCHEM_REFRACTIVITY>
77.8083

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfadoxine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015413
     RDKit          3D
Sulfadoxine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.7768    2.2155   -0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9520    1.6850    0.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8718    0.8535   -0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6151    0.5506   -1.4141 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5807   -0.2494   -1.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -0.7202   -0.7068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -0.4515    0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   -0.9930    1.5964 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0953   -2.0043    1.1548 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.5573   -3.1979    0.3773 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -2.5519    2.3601 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -1.2448    0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2652   -1.3131   -1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -0.7095   -2.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2287    0.0093   -1.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1897    0.6274   -2.2812 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2841    0.1013   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3360   -0.5102    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211    0.3814    0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3715    0.6826    2.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2107   -0.0704    3.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4163    1.9045   -1.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8029    1.8311   -0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7632    3.3208   -0.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747   -0.4942   -2.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3862   -0.7741    2.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4823   -1.8685   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1762   -0.7707   -3.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5727    0.1916   -3.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721    1.5855   -2.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0954    0.6686    0.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -0.4173    1.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0840   -1.1499    2.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8817    0.1274    4.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2642    0.2151    3.0107 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  7 19  2  0
 19 20  1  0
 20 21  1  0
 19  3  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
 21 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1299                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       8.415   1.448   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       9.185   0.114   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.645   2.781   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.414  -0.862   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.414  -3.942   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       7.081   0.678   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       8.415  -1.632   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      13.750   4.528   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       7.081  -3.942   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.748   2.218   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -0.862   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082   1.448   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748   3.758   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -1.632   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.416   2.218   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082   4.528   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.416   3.758   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748  -3.172   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415  -3.172   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080  -1.632   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414  -5.483   0.000  0.00  0.00           C+0
CONECT    1    2    3    6   10                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   14   20                                                       
CONECT    5   18   21                                                       
CONECT    6    1   11                                                       
CONECT    7   11   19                                                       
CONECT    8   17                                                            
CONECT    9   18   19                                                       
CONECT   10    1   12   13                                                  
CONECT   11    6    7   14                                                  
CONECT   12   10   15                                                       
CONECT   13   10   16                                                       
CONECT   14    4   11   18                                                  
CONECT   15   12   17                                                       
CONECT   16   13   17                                                       
CONECT   17    8   15   16                                                  
CONECT   18    5    9   14                                                  
CONECT   19    7    9                                                       
CONECT   20    4                                                            
CONECT   21    5                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0015413
HETATM    1  C1  UNL     1      -4.777   2.216  -0.874  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.952   1.685   0.136  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.872   0.854  -0.129  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.615   0.551  -1.414  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.581  -0.249  -1.711  1.00  0.00           C  
HETATM    6  N2  UNL     1      -0.836  -0.720  -0.707  1.00  0.00           N  
HETATM    7  C4  UNL     1      -1.045  -0.451   0.599  1.00  0.00           C  
HETATM    8  N3  UNL     1      -0.207  -0.993   1.596  1.00  0.00           N  
HETATM    9  S1  UNL     1       1.095  -2.004   1.155  1.00  0.00           S  
HETATM   10  O2  UNL     1       0.557  -3.198   0.377  1.00  0.00           O  
HETATM   11  O3  UNL     1       1.807  -2.552   2.360  1.00  0.00           O  
HETATM   12  C5  UNL     1       2.285  -1.245   0.152  1.00  0.00           C  
HETATM   13  C6  UNL     1       2.265  -1.313  -1.221  1.00  0.00           C  
HETATM   14  C7  UNL     1       3.203  -0.709  -2.033  1.00  0.00           C  
HETATM   15  C8  UNL     1       4.229   0.009  -1.441  1.00  0.00           C  
HETATM   16  N4  UNL     1       5.190   0.627  -2.281  1.00  0.00           N  
HETATM   17  C9  UNL     1       4.284   0.101  -0.074  1.00  0.00           C  
HETATM   18  C10 UNL     1       3.336  -0.510   0.709  1.00  0.00           C  
HETATM   19  C11 UNL     1      -2.121   0.381   0.915  1.00  0.00           C  
HETATM   20  O4  UNL     1      -2.371   0.683   2.235  1.00  0.00           O  
HETATM   21  C12 UNL     1      -3.211  -0.070   3.079  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.416   1.904  -1.878  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.803   1.831  -0.709  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.763   3.321  -0.812  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.375  -0.494  -2.762  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.386  -0.774   2.590  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.482  -1.868  -1.714  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.176  -0.771  -3.110  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.573   0.192  -3.152  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.572   1.586  -2.055  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.095   0.669   0.362  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.410  -0.417   1.779  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.084  -1.150   2.886  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.882   0.127   4.135  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.264   0.215   3.011  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5
CONECT    5    6    6   25
CONECT    6    7
CONECT    7    8   19   19
CONECT    8    9   26
CONECT    9   10   10   11   11
CONECT    9   12
CONECT   12   13   13   18
CONECT   13   14   27
CONECT   14   15   15   28
CONECT   15   16   17
CONECT   16   29   30
CONECT   17   18   18   31
CONECT   18   32
CONECT   19   20
CONECT   20   21
CONECT   21   33   34   35
END

HMDB0015413
     RDKit          3D
Sulfadoxine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.7768    2.2155   -0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9520    1.6850    0.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8718    0.8535   -0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6151    0.5506   -1.4141 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5807   -0.2494   -1.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -0.7202   -0.7068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -0.4515    0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   -0.9930    1.5964 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0953   -2.0043    1.1548 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.5573   -3.1979    0.3773 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -2.5519    2.3601 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -1.2448    0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2652   -1.3131   -1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -0.7095   -2.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2287    0.0093   -1.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1897    0.6274   -2.2812 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2841    0.1013   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3360   -0.5102    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211    0.3814    0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3715    0.6826    2.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2107   -0.0704    3.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4163    1.9045   -1.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8029    1.8311   -0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7632    3.3208   -0.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747   -0.4942   -2.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3862   -0.7741    2.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4823   -1.8685   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1762   -0.7707   -3.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5727    0.1916   -3.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721    1.5855   -2.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0954    0.6686    0.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -0.4173    1.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0840   -1.1499    2.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8817    0.1274    4.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2642    0.2151    3.0107 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  7 19  2  0
 19 20  1  0
 20 21  1  0
 19  3  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
 21 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Sulfanilamido-5,6-dimethoxypyrimidine	ChEBI
Sulfadoxina	ChEBI
Sulfadoxinum	ChEBI
Sulforthomidine	ChEBI
Sulphadoxine	ChEBI
Sulphormethoxine	ChEBI
4-Sulphanilamido-5,6-dimethoxypyrimidine	Generator
Sulphadoxina	Generator
Sulphadoxinum	Generator
Sulphorthomidine	Generator
Sulformethoxine	Generator
Sulfadoxine roche brand	HMDB
Roche brand OF sulfadoxine	HMDB
Sulformetoxine	HMDB
Sulphormetoxin	HMDB
Fanasil	HMDB
Sulphorthodimethoxine	HMDB

Chemical Formula

C₁₂H₁₄N₄O₄S

Average Molecular Weight

310.329

Monoisotopic Molecular Weight

310.073575646

IUPAC Name

4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide

Traditional Name

sulfadoxine

CAS Registry Number

2447-57-6

SMILES

COC1=NC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1OC

InChI Identifier

InChI=1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)

InChI Key

PJSFRIWCGOHTNF-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
Aniline or substituted anilines
Alkyl aryl ether
Pyrimidine
Organosulfonic acid amide
Imidolactam
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Heteroaromatic compound
Organoheterocyclic compound
Ether
Azacycle
Organic oxygen compound
Organic oxide
Amine
Organic nitrogen compound
Organopnictogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:9329 )
pyrimidines (CHEBI:9329 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	190 - 194 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.3 g/L	Not Available
LogP	0.70	SANGSTER (1994)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	165.3	30932474
[M+H]+	Not Available	166.243	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000774

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	0.72	ALOGPS
logP	0.58	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.12	ChemAxon
pKa (Strongest Basic)	2.55	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	116.43 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.81 m³·mol⁻¹	ChemAxon
Polarizability	30.01 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]+	170.843	31661259
DarkChem	[M-H]-	170.926	31661259
DeepCCS	[M+H]+	167.264	30932474
DeepCCS	[M-H]-	164.906	30932474
DeepCCS	[M-2H]-	197.792	30932474
DeepCCS	[M+Na]+	173.357	30932474
AllCCS	[M+H]+	170.7	32859911
AllCCS	[M+H-H2O]+	167.3	32859911
AllCCS	[M+NH4]+	173.8	32859911
AllCCS	[M+Na]+	174.7	32859911
AllCCS	[M-H]-	167.2	32859911
AllCCS	[M+Na-2H]-	167.2	32859911
AllCCS	[M+HCOO]-	167.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sulfadoxine	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1OC	4362.2	Standard polar	33892256
Sulfadoxine	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1OC	2842.9	Standard non polar	33892256
Sulfadoxine	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1OC	2766.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sulfadoxine,1TMS,isomer #1	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=C1OC	3006.8	Semi standard non polar	33892256
Sulfadoxine,1TMS,isomer #1	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=C1OC	2754.2	Standard non polar	33892256
Sulfadoxine,1TMS,isomer #1	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=C1OC	4375.8	Standard polar	33892256
Sulfadoxine,1TMS,isomer #2	COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=C1OC	2735.6	Semi standard non polar	33892256
Sulfadoxine,1TMS,isomer #2	COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=C1OC	2685.9	Standard non polar	33892256
Sulfadoxine,1TMS,isomer #2	COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=C1OC	4480.9	Standard polar	33892256
Sulfadoxine,2TMS,isomer #1	COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=C1OC	2800.6	Semi standard non polar	33892256
Sulfadoxine,2TMS,isomer #1	COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=C1OC	2808.8	Standard non polar	33892256
Sulfadoxine,2TMS,isomer #1	COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=C1OC	3887.0	Standard polar	33892256
Sulfadoxine,2TMS,isomer #2	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=C1OC	2827.2	Semi standard non polar	33892256
Sulfadoxine,2TMS,isomer #2	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=C1OC	2842.7	Standard non polar	33892256
Sulfadoxine,2TMS,isomer #2	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=C1OC	4054.7	Standard polar	33892256
Sulfadoxine,3TMS,isomer #1	COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=C1OC	2726.4	Semi standard non polar	33892256
Sulfadoxine,3TMS,isomer #1	COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=C1OC	2936.2	Standard non polar	33892256
Sulfadoxine,3TMS,isomer #1	COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=C1OC	3639.3	Standard polar	33892256
Sulfadoxine,1TBDMS,isomer #1	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=C1OC	3246.6	Semi standard non polar	33892256
Sulfadoxine,1TBDMS,isomer #1	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=C1OC	2978.7	Standard non polar	33892256
Sulfadoxine,1TBDMS,isomer #1	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=C1OC	4334.8	Standard polar	33892256
Sulfadoxine,1TBDMS,isomer #2	COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=C1OC	3000.4	Semi standard non polar	33892256
Sulfadoxine,1TBDMS,isomer #2	COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=C1OC	2905.1	Standard non polar	33892256
Sulfadoxine,1TBDMS,isomer #2	COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=C1OC	4413.8	Standard polar	33892256
Sulfadoxine,2TBDMS,isomer #1	COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=C1OC	3258.0	Semi standard non polar	33892256
Sulfadoxine,2TBDMS,isomer #1	COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=C1OC	3276.6	Standard non polar	33892256
Sulfadoxine,2TBDMS,isomer #1	COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=C1OC	3883.6	Standard polar	33892256
Sulfadoxine,2TBDMS,isomer #2	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=C1OC	3297.7	Semi standard non polar	33892256
Sulfadoxine,2TBDMS,isomer #2	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=C1OC	3259.5	Standard non polar	33892256
Sulfadoxine,2TBDMS,isomer #2	COC1=NC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=C1OC	3992.2	Standard polar	33892256
Sulfadoxine,3TBDMS,isomer #1	COC1=NC=NC(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)=C1OC	3374.9	Semi standard non polar	33892256
Sulfadoxine,3TBDMS,isomer #1	COC1=NC=NC(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)=C1OC	3633.1	Standard non polar	33892256
Sulfadoxine,3TBDMS,isomer #1	COC1=NC=NC(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)=C1OC	3724.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfadoxine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pb9-4960000000-7bae9693017c80170870	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfadoxine 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 - Sulfadoxine LC-ESI-qTof , Positive-QTOF	splash10-0a4i-3910000000-fbde0b31ef009afef44d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfadoxine LC-ESI-QTOF , positive-QTOF	splash10-0a4i-2901000000-8862dd6e93b57f07349b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfadoxine , positive-QTOF	splash10-0a4i-3910000000-fbde0b31ef009afef44d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfadoxine -1V, Positive-QTOF	splash10-0a4i-2901000000-829e3509a57184006d4d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfadoxine 10V, Positive-QTOF	splash10-03di-0309000000-1bd412483b026d7d74f0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfadoxine 20V, Positive-QTOF	splash10-0a4i-0912000000-5c0e441629572b2c03c8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfadoxine 40V, Positive-QTOF	splash10-00mo-9410000000-b0f2c57374fa57bcb8f8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfadoxine 10V, Negative-QTOF	splash10-0a4i-0009000000-02a2edbc525ff42bef1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfadoxine 20V, Negative-QTOF	splash10-0a6r-2195000000-24e8009c9a6ac8dcb544	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfadoxine 40V, Negative-QTOF	splash10-06dl-9850000000-961491cd3503d195810e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfadoxine 10V, Positive-QTOF	splash10-03di-0009000000-ba17475c1b8cfb24cbba	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfadoxine 20V, Positive-QTOF	splash10-0a4i-1903000000-4e317eeecd7fc60855a4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfadoxine 40V, Positive-QTOF	splash10-00kf-9500000000-cfa956a4cdadb48dcd01	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfadoxine 10V, Negative-QTOF	splash10-0a4i-0009000000-9966f01da719564fa0a5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfadoxine 20V, Negative-QTOF	splash10-0a4i-1759000000-2dc8060f61a784f23466	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfadoxine 40V, Negative-QTOF	splash10-0a4i-4900000000-6f4adc5fd2e7a1ae7504	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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 DB01299	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01299	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01299

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16218

KEGG Compound ID

C07630

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulfadoxine

METLIN ID

Not Available

PubChem Compound

17134

PDB ID

Not Available

ChEBI ID

9329

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Sulfadoxine (HMDB0015413)

MOL for HMDB0015413 (Sulfadoxine)

3D MOL for HMDB0015413 (Sulfadoxine)

3D SDF for HMDB0015413 (Sulfadoxine)

3D-SDF for HMDB0015413 (Sulfadoxine)

PDB for HMDB0015413 (Sulfadoxine)

3D PDB for HMDB0015413 (Sulfadoxine)

SMILES for HMDB0015413 (Sulfadoxine)

INCHI for HMDB0015413 (Sulfadoxine)

Structure for HMDB0015413 (Sulfadoxine)

3D Structure for HMDB0015413 (Sulfadoxine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra