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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 02:52:00 UTC

HMDB ID

HMDB0015521

Secondary Accession Numbers

HMDB15521

Metabolite Identification

Common Name

Sulfamerazine

Description

Sulfamerazine is only found in individuals that have used or taken this drug.It is a sulfanilamide that is used as an antibacterial agent. [PubChem]Sulfamerazine is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). Sulfamerazine is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA.

Structure

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

HMDB0015521
     RDKit          3D
Sulfamerazine
 30 31  0  0  0  0  0  0  0  0999 V2000
   -2.5644    2.1690   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6289    0.7052   -0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6368    0.1514   -0.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791   -1.2047   -1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8077   -2.0074   -0.4686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8275   -1.4811    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9035   -2.3389    0.9177 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858   -1.7253    1.8976 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.2374   -0.8964    3.0035 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212   -2.8458    2.5723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4436   -0.7263    0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2941    0.6406    0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1501    1.3915    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1904    0.8366   -0.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0582    1.6439   -1.4604 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3492   -0.5300   -0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4983   -1.2877    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7726   -0.1447    0.3902 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5914    2.6497   -1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6345    2.5069    0.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417    2.5964    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3707    0.7444   -1.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4608   -1.6655   -1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0304   -3.3763    0.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4840    1.1438    1.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0401    2.4731   -0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0483    1.3684   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7448    2.5412   -1.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -0.9788   -1.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6126   -2.3529    0.2861 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  6 18  2  0
 18  2  1  0
 17 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

1581
  Mrv0541 02231215342D          

 18 19  0  0  0  0            999 V2000
    2.4751    0.1279    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    0.9529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    0.9529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -3.1722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -2.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    3.4280    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  4  1  0  0  0  0
  1  8  1  0  0  0  0
  4 14  1  0  0  0  0
  5 14  1  0  0  0  0
  5 15  2  0  0  0  0
  6 14  2  0  0  0  0
  6 17  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  2  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 15 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015521

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N4O2S/c1-8-6-7-13-11(14-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)

> <INCHI_KEY>
QPPBRPIAZZHUNT-UHFFFAOYSA-N

> <FORMULA>
C11H12N4O2S

> <MOLECULAR_WEIGHT>
264.304

> <EXACT_MASS>
264.068096338

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.506703454094367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-N-(4-methylpyrimidin-2-yl)benzene-1-sulfonamide

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.518630977

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.991748059703492

> <JCHEM_PKA_STRONGEST_BASIC>
2.0112004528347196

> <JCHEM_POLAR_SURFACE_AREA>
97.97

> <JCHEM_REFRACTIVITY>
68.79240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfamerazine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015521
     RDKit          3D
Sulfamerazine
 30 31  0  0  0  0  0  0  0  0999 V2000
   -2.5644    2.1690   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6289    0.7052   -0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6368    0.1514   -0.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791   -1.2047   -1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8077   -2.0074   -0.4686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8275   -1.4811    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9035   -2.3389    0.9177 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858   -1.7253    1.8976 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.2374   -0.8964    3.0035 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212   -2.8458    2.5723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4436   -0.7263    0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2941    0.6406    0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1501    1.3915    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1904    0.8366   -0.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0582    1.6439   -1.4604 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3492   -0.5300   -0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4983   -1.2877    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7726   -0.1447    0.3902 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5914    2.6497   -1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6345    2.5069    0.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417    2.5964    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3707    0.7444   -1.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4608   -1.6655   -1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0304   -3.3763    0.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4840    1.1438    1.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0401    2.4731   -0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0483    1.3684   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7448    2.5412   -1.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -0.9788   -1.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6126   -2.3529    0.2861 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  6 18  2  0
 18  2  1  0
 17 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1581                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.620   0.239   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       3.080   0.239   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.160   0.239   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.620   1.779   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.954   4.089   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.288   1.779   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       4.620  -5.921   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.620  -1.301   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.286  -2.071   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.954  -2.071   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.620  -4.381   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.286  -3.611   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.954  -3.611   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.954   2.549   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.288   4.859   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.621   4.089   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.621   2.549   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.288   6.399   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    8                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1   14                                                       
CONECT    5   14   15                                                       
CONECT    6   14   17                                                       
CONECT    7   11                                                            
CONECT    8    1    9   10                                                  
CONECT    9    8   12                                                       
CONECT   10    8   13                                                       
CONECT   11    7   12   13                                                  
CONECT   12    9   11                                                       
CONECT   13   10   11                                                       
CONECT   14    4    5    6                                                  
CONECT   15    5   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17    6   16                                                       
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0015521
HETATM    1  C1  UNL     1      -2.564   2.169  -0.073  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.629   0.705  -0.196  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.637   0.151  -0.967  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.679  -1.205  -1.069  1.00  0.00           C  
HETATM    5  N1  UNL     1      -2.808  -2.007  -0.469  1.00  0.00           N  
HETATM    6  C5  UNL     1      -1.827  -1.481   0.280  1.00  0.00           C  
HETATM    7  N2  UNL     1      -0.904  -2.339   0.918  1.00  0.00           N  
HETATM    8  S1  UNL     1       0.386  -1.725   1.898  1.00  0.00           S  
HETATM    9  O1  UNL     1      -0.237  -0.896   3.004  1.00  0.00           O  
HETATM   10  O2  UNL     1       1.121  -2.846   2.572  1.00  0.00           O  
HETATM   11  C6  UNL     1       1.444  -0.726   0.930  1.00  0.00           C  
HETATM   12  C7  UNL     1       1.294   0.641   0.830  1.00  0.00           C  
HETATM   13  C8  UNL     1       2.150   1.392   0.051  1.00  0.00           C  
HETATM   14  C9  UNL     1       3.190   0.837  -0.664  1.00  0.00           C  
HETATM   15  N3  UNL     1       4.058   1.644  -1.460  1.00  0.00           N  
HETATM   16  C10 UNL     1       3.349  -0.530  -0.570  1.00  0.00           C  
HETATM   17  C11 UNL     1       2.498  -1.288   0.206  1.00  0.00           C  
HETATM   18  N4  UNL     1      -1.773  -0.145   0.390  1.00  0.00           N  
HETATM   19  H1  UNL     1      -2.591   2.650  -1.083  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.634   2.507   0.408  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.442   2.596   0.471  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.371   0.744  -1.477  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.461  -1.666  -1.668  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.030  -3.376   0.772  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.484   1.144   1.379  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.040   2.473  -0.035  1.00  0.00           H  
HETATM   27  H9  UNL     1       5.048   1.368  -1.645  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.745   2.541  -1.892  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.167  -0.979  -1.129  1.00  0.00           H  
HETATM   30  H12 UNL     1       2.613  -2.353   0.286  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   18
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6
CONECT    6    7   18   18
CONECT    7    8   24
CONECT    8    9    9   10   10
CONECT    8   11
CONECT   11   12   12   17
CONECT   12   13   25
CONECT   13   14   14   26
CONECT   14   15   16
CONECT   15   27   28
CONECT   16   17   17   29
CONECT   17   30
END

HMDB0015521
     RDKit          3D
Sulfamerazine
 30 31  0  0  0  0  0  0  0  0999 V2000
   -2.5644    2.1690   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6289    0.7052   -0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6368    0.1514   -0.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791   -1.2047   -1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8077   -2.0074   -0.4686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8275   -1.4811    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9035   -2.3389    0.9177 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858   -1.7253    1.8976 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.2374   -0.8964    3.0035 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212   -2.8458    2.5723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4436   -0.7263    0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2941    0.6406    0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1501    1.3915    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1904    0.8366   -0.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0582    1.6439   -1.4604 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3492   -0.5300   -0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4983   -1.2877    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7726   -0.1447    0.3902 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5914    2.6497   -1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6345    2.5069    0.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417    2.5964    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3707    0.7444   -1.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4608   -1.6655   -1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0304   -3.3763    0.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4840    1.1438    1.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0401    2.4731   -0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0483    1.3684   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7448    2.5412   -1.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -0.9788   -1.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6126   -2.3529    0.2861 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  6 18  2  0
 18  2  1  0
 17 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(p-Aminobenzolsulfonyl)-2-amino-4-methylpyrimidin	ChEBI
2-(4-Aminobenzenesulfonamido)-4-methylpyrimidine	ChEBI
2-(p-Aminobenzolsulfonamido)-4-methylpyrimidine	ChEBI
2-(Sulfanilamido)-4-methylpyrimidine	ChEBI
2-Sulfa-4-methylpyrimidine	ChEBI
4-Amino-N-(4-methyl-2-pyrimidinyl)-benzenesulfonamide	ChEBI
N-(4-Methyl-2-pyrimidyl)sulfanilamide	ChEBI
N(1)-(4-Methyl-2-pyrimidinyl)sulfanilamide	ChEBI
Sulfamerazina	ChEBI
Sulfamerazinum	ChEBI
Sulfamethyldiazine	ChEBI
Sulphamerazine	ChEBI
(p-Aminobenzolsulphonyl)-2-amino-4-methylpyrimidin	Generator
2-(4-Aminobenzenesulphonamido)-4-methylpyrimidine	Generator
2-(p-Aminobenzolsulphonamido)-4-methylpyrimidine	Generator
2-(Sulphanilamido)-4-methylpyrimidine	Generator
2-Sulpha-4-methylpyrimidine	Generator
4-Amino-N-(4-methyl-2-pyrimidinyl)-benzenesulphonamide	Generator
N-(4-Methyl-2-pyrimidyl)sulphanilamide	Generator
N(1)-(4-Methyl-2-pyrimidinyl)sulphanilamide	Generator
Sulphamerazina	Generator
Sulphamerazinum	Generator
Sulphamethyldiazine	Generator
Sulfamerazine veyx brand	HMDB
Trimetox	HMDB
Veyx brand OF sulfamerazine	HMDB
Methylsulfadiazine	HMDB
Mebacid	HMDB

Chemical Formula

C₁₁H₁₂N₄O₂S

Average Molecular Weight

264.304

Monoisotopic Molecular Weight

264.068096338

IUPAC Name

4-amino-N-(4-methylpyrimidin-2-yl)benzene-1-sulfonamide

Traditional Name

sulfamerazine

CAS Registry Number

127-79-7

SMILES

CC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C1

InChI Identifier

InChI=1S/C11H12N4O2S/c1-8-6-7-13-11(14-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)

InChI Key

QPPBRPIAZZHUNT-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
Pyrimidine
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Heteroaromatic compound
Aminosulfonyl compound
Sulfonyl
Azacycle
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organosulfur compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:102130 )
pyrimidines (CHEBI:102130 )
sulfonamide antibiotic (CHEBI:102130 )

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

Extracellular (HMDB: HMDB0015521)

Source

Exogenous

Exogenous (HMDB: HMDB0015521)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	236 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.3 g/L	Not Available
LogP	0.14	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	156.267	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000816

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	0.44	ALOGPS
logP	0.52	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	6.99	ChemAxon
pKa (Strongest Basic)	2.01	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.79 m³·mol⁻¹	ChemAxon
Polarizability	26.51 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	161.622	31661259
DarkChem	[M-H]-	163.227	31661259
DeepCCS	[M+H]+	159.796	30932474
DeepCCS	[M-H]-	157.438	30932474
DeepCCS	[M-2H]-	190.324	30932474
DeepCCS	[M+Na]+	165.89	30932474
AllCCS	[M+H]+	160.7	32859911
AllCCS	[M+H-H2O]+	156.9	32859911
AllCCS	[M+NH4]+	164.1	32859911
AllCCS	[M+Na]+	165.1	32859911
AllCCS	[M-H]-	157.1	32859911
AllCCS	[M+Na-2H]-	157.1	32859911
AllCCS	[M+HCOO]-	157.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.79 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8885 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.06 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	617.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	232.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	80.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	156.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	41.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	237.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	302.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	110.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	619.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	45.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	812.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	192.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	208.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	411.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	247.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	295.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sulfamerazine	CC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C1	4087.6	Standard polar	33892256
Sulfamerazine	CC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C1	2548.2	Standard non polar	33892256
Sulfamerazine	CC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C1	2541.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sulfamerazine,1TMS,isomer #1	CC1=CC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N1	2778.7	Semi standard non polar	33892256
Sulfamerazine,1TMS,isomer #1	CC1=CC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N1	2462.0	Standard non polar	33892256
Sulfamerazine,1TMS,isomer #1	CC1=CC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N1	3726.0	Standard polar	33892256
Sulfamerazine,1TMS,isomer #2	CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N1	2543.6	Semi standard non polar	33892256
Sulfamerazine,1TMS,isomer #2	CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N1	2419.7	Standard non polar	33892256
Sulfamerazine,1TMS,isomer #2	CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N1	3876.8	Standard polar	33892256
Sulfamerazine,2TMS,isomer #1	CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N1	2550.1	Semi standard non polar	33892256
Sulfamerazine,2TMS,isomer #1	CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N1	2537.0	Standard non polar	33892256
Sulfamerazine,2TMS,isomer #1	CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N1	3399.2	Standard polar	33892256
Sulfamerazine,2TMS,isomer #2	CC1=CC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N1	2573.3	Semi standard non polar	33892256
Sulfamerazine,2TMS,isomer #2	CC1=CC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N1	2552.2	Standard non polar	33892256
Sulfamerazine,2TMS,isomer #2	CC1=CC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N1	3523.6	Standard polar	33892256
Sulfamerazine,3TMS,isomer #1	CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N1	2437.9	Semi standard non polar	33892256
Sulfamerazine,3TMS,isomer #1	CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N1	2655.3	Standard non polar	33892256
Sulfamerazine,3TMS,isomer #1	CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N1	3246.1	Standard polar	33892256
Sulfamerazine,1TBDMS,isomer #1	CC1=CC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N1	3005.9	Semi standard non polar	33892256
Sulfamerazine,1TBDMS,isomer #1	CC1=CC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N1	2684.6	Standard non polar	33892256
Sulfamerazine,1TBDMS,isomer #1	CC1=CC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N1	3768.3	Standard polar	33892256
Sulfamerazine,1TBDMS,isomer #2	CC1=CC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N1	2793.4	Semi standard non polar	33892256
Sulfamerazine,1TBDMS,isomer #2	CC1=CC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N1	2638.0	Standard non polar	33892256
Sulfamerazine,1TBDMS,isomer #2	CC1=CC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N1	3854.4	Standard polar	33892256
Sulfamerazine,2TBDMS,isomer #1	CC1=CC=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)=N1	3004.0	Semi standard non polar	33892256
Sulfamerazine,2TBDMS,isomer #1	CC1=CC=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)=N1	2984.6	Standard non polar	33892256
Sulfamerazine,2TBDMS,isomer #1	CC1=CC=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)=N1	3475.9	Standard polar	33892256
Sulfamerazine,2TBDMS,isomer #2	CC1=CC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N1	3094.2	Semi standard non polar	33892256
Sulfamerazine,2TBDMS,isomer #2	CC1=CC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N1	2980.8	Standard non polar	33892256
Sulfamerazine,2TBDMS,isomer #2	CC1=CC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N1	3555.3	Standard polar	33892256
Sulfamerazine,3TBDMS,isomer #1	CC1=CC=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)=N1	3149.5	Semi standard non polar	33892256
Sulfamerazine,3TBDMS,isomer #1	CC1=CC=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)=N1	3338.5	Standard non polar	33892256
Sulfamerazine,3TBDMS,isomer #1	CC1=CC=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)=N1	3398.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfamerazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9630000000-7f08d04a103b7e16f126	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfamerazine 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 - Sulfamerazine LC-ESI-qTof , Positive-QTOF	splash10-0bt9-4900000000-1429f19666bf05cae962	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamerazine LC-ESI-QTOF , positive-QTOF	splash10-0aou-1920000000-06a82249586c8821f9d3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamerazine , positive-QTOF	splash10-0bt9-4900000000-1429f19666bf05cae962	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfamerazine -1V, Positive-QTOF	splash10-0aou-1920000000-418893a0c51582391ad4	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamerazine 10V, Positive-QTOF	splash10-014i-0190000000-74f76987a0c498d6bca1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamerazine 20V, Positive-QTOF	splash10-066r-2960000000-fe211aa71f3a8480b97c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamerazine 40V, Positive-QTOF	splash10-00mo-9100000000-7b53bc2852347d4eb65a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamerazine 10V, Negative-QTOF	splash10-03di-0090000000-c8b827438334ef9362a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamerazine 20V, Negative-QTOF	splash10-03dj-1590000000-abc72f9a326e9106f00f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamerazine 40V, Negative-QTOF	splash10-0006-9400000000-adca0ea9c658e9952d5a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamerazine 10V, Positive-QTOF	splash10-014i-0090000000-d2eef97caf4d75ad8466	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamerazine 20V, Positive-QTOF	splash10-052f-9430000000-d161431499729de125e0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamerazine 40V, Positive-QTOF	splash10-014l-9000000000-246c8431b9069be15277	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamerazine 10V, Negative-QTOF	splash10-03di-0090000000-961f60caf9f0b5d9c607	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamerazine 20V, Negative-QTOF	splash10-03di-1290000000-fff5d1edd43fea6c5e0b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfamerazine 40V, Negative-QTOF	splash10-014l-9200000000-652240a00ecd796e0b7b	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

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 DB01581	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01581	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01581

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5134

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulfamerazine

METLIN ID

Not Available

PubChem Compound

5325

PDB ID

Not Available

ChEBI ID

102130

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)

Download (PDF)

General References

Not Available

Showing metabocard for Sulfamerazine (HMDB0015521)

MOL for HMDB0015521 (Sulfamerazine)

3D MOL for HMDB0015521 (Sulfamerazine)

3D SDF for HMDB0015521 (Sulfamerazine)

3D-SDF for HMDB0015521 (Sulfamerazine)

PDB for HMDB0015521 (Sulfamerazine)

3D PDB for HMDB0015521 (Sulfamerazine)

SMILES for HMDB0015521 (Sulfamerazine)

INCHI for HMDB0015521 (Sulfamerazine)

Structure for HMDB0015521 (Sulfamerazine)

3D Structure for HMDB0015521 (Sulfamerazine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra