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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014802

Secondary Accession Numbers

HMDB14802

Metabolite Identification

Common Name

Sulfametopyrazine

Description

Sulfametopyrazine is only found in individuals that have used or taken this drug. It is a long-acting plasma-bound sulfonamide used for respiratory and urinary tract infections and also for malaria. [PubChem]Sulfametopyrazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. Para-aminobenzoic acid (PABA), a substrate of the enzyme is prevented from binding. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.

Structure

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

HMDB0014802
     RDKit          3D
Sulfametopyrazine
 31 32  0  0  0  0  0  0  0  0999 V2000
   -4.5003   -1.6443    1.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013   -0.8998    1.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8628   -0.2700    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5751   -0.3388   -0.6912 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    0.2534   -1.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9904    0.9630   -1.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608    1.0387   -0.6617 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843    0.4243    0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9095    0.5001    1.6716 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.3714    1.7103 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.0936    1.3443    3.1328 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2843    2.8191    1.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7741    0.7358    0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9506    1.2175   -0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9107    0.6897   -1.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7438   -0.3421   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7255   -0.8738   -2.0067 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5686   -0.8268    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6147   -0.3070    1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3579   -2.5849    2.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8167   -1.9474    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2716   -1.0415    2.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937    0.1734   -2.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7023    1.4355   -2.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2784    0.0091    2.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3122    2.0291   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0330    1.0807   -2.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2846   -0.3114   -2.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9018   -1.8975   -1.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2321   -1.6477    0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -0.7057    2.0197 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  2  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  8  3  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
 14 26  1  0
 15 27  1  0
 17 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

664
  Mrv0541 02231214542D          

 19 20  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    2.6029    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
    3.9041    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
    3.9041    2.6029    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
    3.1895    1.3654    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    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
    4.6185    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    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  5  1  0  0  0  0
  1  9  1  0  0  0  0
  4 16  1  0  0  0  0
  4 19  1  0  0  0  0
  5 12  1  0  0  0  0
  6 12  2  0  0  0  0
  6 17  1  0  0  0  0
  7 13  1  0  0  0  0
  8 16  2  0  0  0  0
  8 18  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 12 16  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014802

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N4O3S/c1-18-11-10(13-6-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)

> <INCHI_KEY>
KXRZBTAEDBELFD-UHFFFAOYSA-N

> <FORMULA>
C11H12N4O3S

> <MOLECULAR_WEIGHT>
280.303

> <EXACT_MASS>
280.06301096

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
27.12127477105563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-N-(3-methoxypyrazin-2-yl)benzene-1-sulfonamide

> <ALOGPS_LOGP>
0.41

> <JCHEM_LOGP>
0.2278840863333335

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.914239766872234

> <JCHEM_PKA_STRONGEST_BASIC>
1.9754926220992646

> <JCHEM_POLAR_SURFACE_AREA>
107.2

> <JCHEM_REFRACTIVITY>
70.36700000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
longum

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014802
     RDKit          3D
Sulfametopyrazine
 31 32  0  0  0  0  0  0  0  0999 V2000
   -4.5003   -1.6443    1.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013   -0.8998    1.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8628   -0.2700    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5751   -0.3388   -0.6912 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    0.2534   -1.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9904    0.9630   -1.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608    1.0387   -0.6617 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843    0.4243    0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9095    0.5001    1.6716 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.3714    1.7103 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.0936    1.3443    3.1328 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2843    2.8191    1.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7741    0.7358    0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9506    1.2175   -0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9107    0.6897   -1.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7438   -0.3421   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7255   -0.8738   -2.0067 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5686   -0.8268    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6147   -0.3070    1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3579   -2.5849    2.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8167   -1.9474    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2716   -1.0415    2.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937    0.1734   -2.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7023    1.4355   -2.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2784    0.0091    2.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3122    2.0291   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0330    1.0807   -2.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2846   -0.3114   -2.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9018   -1.8975   -1.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2321   -1.6477    0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -0.7057    2.0197 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  2  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  8  3  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
 14 26  1  0
 15 27  1  0
 17 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 664                                               
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  O   UNK     0       4.620   4.859   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.620   1.779   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  N   UNK     0       7.288   4.859   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.620  -1.301   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.286  -2.071   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.954  -2.071   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.954   2.549   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.620  -4.381   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.286  -3.611   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.954  -3.611   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.954   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       8.621   4.089   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.620   6.399   0.000  0.00  0.00           C+0
CONECT    1    2    3    5    9                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   16   19                                                       
CONECT    5    1   12                                                       
CONECT    6   12   17                                                       
CONECT    7   13                                                            
CONECT    8   16   18                                                       
CONECT    9    1   10   11                                                  
CONECT   10    9   14                                                       
CONECT   11    9   15                                                       
CONECT   12    5    6   16                                                  
CONECT   13    7   14   15                                                  
CONECT   14   10   13                                                       
CONECT   15   11   13                                                       
CONECT   16    4    8   12                                                  
CONECT   17    6   18                                                       
CONECT   18    8   17                                                       
CONECT   19    4                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0014802
HETATM    1  C1  UNL     1      -4.500  -1.644   1.648  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.301  -0.900   1.567  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.863  -0.270   0.424  1.00  0.00           C  
HETATM    4  N1  UNL     1      -3.575  -0.339  -0.691  1.00  0.00           N  
HETATM    5  C3  UNL     1      -3.184   0.253  -1.806  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.990   0.963  -1.788  1.00  0.00           C  
HETATM    7  N2  UNL     1      -1.261   1.039  -0.662  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.684   0.424   0.461  1.00  0.00           C  
HETATM    9  N3  UNL     1      -0.910   0.500   1.672  1.00  0.00           N  
HETATM   10  S1  UNL     1       0.568   1.371   1.710  1.00  0.00           S  
HETATM   11  O2  UNL     1       1.094   1.344   3.133  1.00  0.00           O  
HETATM   12  O3  UNL     1       0.284   2.819   1.405  1.00  0.00           O  
HETATM   13  C6  UNL     1       1.774   0.736   0.614  1.00  0.00           C  
HETATM   14  C7  UNL     1       1.951   1.217  -0.666  1.00  0.00           C  
HETATM   15  C8  UNL     1       2.911   0.690  -1.511  1.00  0.00           C  
HETATM   16  C9  UNL     1       3.744  -0.342  -1.128  1.00  0.00           C  
HETATM   17  N4  UNL     1       4.726  -0.874  -2.007  1.00  0.00           N  
HETATM   18  C10 UNL     1       3.569  -0.827   0.157  1.00  0.00           C  
HETATM   19  C11 UNL     1       2.615  -0.307   1.005  1.00  0.00           C  
HETATM   20  H1  UNL     1      -4.358  -2.585   2.230  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.817  -1.947   0.631  1.00  0.00           H  
HETATM   22  H3  UNL     1      -5.272  -1.041   2.180  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.794   0.173  -2.695  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.702   1.436  -2.722  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.278   0.009   2.515  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.312   2.029  -0.989  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.033   1.081  -2.510  1.00  0.00           H  
HETATM   28  H9  UNL     1       5.285  -0.311  -2.677  1.00  0.00           H  
HETATM   29  H10 UNL     1       4.902  -1.898  -1.982  1.00  0.00           H  
HETATM   30  H11 UNL     1       4.232  -1.648   0.460  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.492  -0.706   2.020  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5
CONECT    5    6    6   23
CONECT    6    7   24
CONECT    7    8    8
CONECT    8    9
CONECT    9   10   25
CONECT   10   11   11   12   12
CONECT   10   13
CONECT   13   14   14   19
CONECT   14   15   26
CONECT   15   16   16   27
CONECT   16   17   18
CONECT   17   28   29
CONECT   18   19   19   30
CONECT   19   31
END

HMDB0014802
     RDKit          3D
Sulfametopyrazine
 31 32  0  0  0  0  0  0  0  0999 V2000
   -4.5003   -1.6443    1.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013   -0.8998    1.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8628   -0.2700    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5751   -0.3388   -0.6912 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    0.2534   -1.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9904    0.9630   -1.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608    1.0387   -0.6617 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843    0.4243    0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9095    0.5001    1.6716 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.3714    1.7103 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.0936    1.3443    3.1328 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2843    2.8191    1.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7741    0.7358    0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9506    1.2175   -0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9107    0.6897   -1.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7438   -0.3421   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7255   -0.8738   -2.0067 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5686   -0.8268    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6147   -0.3070    1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3579   -2.5849    2.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8167   -1.9474    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2716   -1.0415    2.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937    0.1734   -2.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7023    1.4355   -2.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2784    0.0091    2.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3122    2.0291   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0330    1.0807   -2.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2846   -0.3114   -2.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9018   -1.8975   -1.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2321   -1.6477    0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -0.7057    2.0197 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  2  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  8  3  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
 14 26  1  0
 15 27  1  0
 17 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Sulfalene	Kegg
Sulfamethopyrazine	Kegg
Kelfizina	Kegg
Sulphalene	Generator
Sulphamethopyrazine	Generator
Sulphametopyrazine	Generator
Pharmacia brand OF sulfalene	HMDB
Sulfapyrazinmethoxine	HMDB
Longum	HMDB
Sulfamethoxypyrazine	HMDB
Kelfizine	HMDB
Sulfametopyrazine	MeSH

Chemical Formula

C₁₁H₁₂N₄O₃S

Average Molecular Weight

280.303

Monoisotopic Molecular Weight

280.06301096

IUPAC Name

4-amino-N-(3-methoxypyrazin-2-yl)benzene-1-sulfonamide

Traditional Name

longum

CAS Registry Number

152-47-6

SMILES

COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1

InChI Identifier

InChI=1S/C11H12N4O3S/c1-18-11-10(13-6-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)

InChI Key

KXRZBTAEDBELFD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
Benzenesulfonyl group
Methoxypyrazine
Aniline or substituted anilines
Alkyl aryl ether
Pyrazine
Imidolactam
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Heteroaromatic compound
Ether
Organoheterocyclic compound
Azacycle
Amine
Organic nitrogen compound
Organic oxide
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazines (CHEBI:32162 )
sulfonamide (CHEBI:32162 )
sulfonamide antibiotic (CHEBI:32162 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Source

Exogenous

Exogenous (HMDB: HMDB0014802)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	169.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.41 g/L	Not Available
LogP	0.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.41 g/L	ALOGPS
logP	0.41	ALOGPS
logP	0.23	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	5.91	ChemAxon
pKa (Strongest Basic)	1.98	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	107.2 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	70.37 m³·mol⁻¹	ChemAxon
Polarizability	27.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	162.742	31661259
DarkChem	[M-H]-	163.433	31661259
DeepCCS	[M+H]+	164.798	30932474
DeepCCS	[M-H]-	162.44	30932474
DeepCCS	[M-2H]-	195.332	30932474
DeepCCS	[M+Na]+	170.891	30932474
AllCCS	[M+H]+	163.7	32859911
AllCCS	[M+H-H2O]+	160.1	32859911
AllCCS	[M+NH4]+	167.1	32859911
AllCCS	[M+Na]+	168.0	32859911
AllCCS	[M-H]-	159.5	32859911
AllCCS	[M+Na-2H]-	159.4	32859911
AllCCS	[M+HCOO]-	159.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sulfametopyrazine	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1	4065.1	Standard polar	33892256
Sulfametopyrazine	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1	2698.4	Standard non polar	33892256
Sulfametopyrazine	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1	2569.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sulfametopyrazine,1TMS,isomer #1	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	2847.7	Semi standard non polar	33892256
Sulfametopyrazine,1TMS,isomer #1	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	2589.5	Standard non polar	33892256
Sulfametopyrazine,1TMS,isomer #1	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	4196.7	Standard polar	33892256
Sulfametopyrazine,1TMS,isomer #2	COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	2595.6	Semi standard non polar	33892256
Sulfametopyrazine,1TMS,isomer #2	COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	2523.9	Standard non polar	33892256
Sulfametopyrazine,1TMS,isomer #2	COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	4173.3	Standard polar	33892256
Sulfametopyrazine,2TMS,isomer #1	COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	2669.2	Semi standard non polar	33892256
Sulfametopyrazine,2TMS,isomer #1	COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	2634.6	Standard non polar	33892256
Sulfametopyrazine,2TMS,isomer #1	COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	3651.5	Standard polar	33892256
Sulfametopyrazine,2TMS,isomer #2	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	2687.7	Semi standard non polar	33892256
Sulfametopyrazine,2TMS,isomer #2	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	2669.7	Standard non polar	33892256
Sulfametopyrazine,2TMS,isomer #2	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	3974.6	Standard polar	33892256
Sulfametopyrazine,3TMS,isomer #1	COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	2590.6	Semi standard non polar	33892256
Sulfametopyrazine,3TMS,isomer #1	COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	2756.9	Standard non polar	33892256
Sulfametopyrazine,3TMS,isomer #1	COC1=NC=CN=C1N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	3450.3	Standard polar	33892256
Sulfametopyrazine,1TBDMS,isomer #1	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	3081.9	Semi standard non polar	33892256
Sulfametopyrazine,1TBDMS,isomer #1	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	2813.4	Standard non polar	33892256
Sulfametopyrazine,1TBDMS,isomer #1	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4212.9	Standard polar	33892256
Sulfametopyrazine,1TBDMS,isomer #2	COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	2848.8	Semi standard non polar	33892256
Sulfametopyrazine,1TBDMS,isomer #2	COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	2737.8	Standard non polar	33892256
Sulfametopyrazine,1TBDMS,isomer #2	COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	4131.9	Standard polar	33892256
Sulfametopyrazine,2TBDMS,isomer #1	COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	3094.2	Semi standard non polar	33892256
Sulfametopyrazine,2TBDMS,isomer #1	COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	3092.9	Standard non polar	33892256
Sulfametopyrazine,2TBDMS,isomer #1	COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	3688.5	Standard polar	33892256
Sulfametopyrazine,2TBDMS,isomer #2	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3162.6	Semi standard non polar	33892256
Sulfametopyrazine,2TBDMS,isomer #2	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3094.1	Standard non polar	33892256
Sulfametopyrazine,2TBDMS,isomer #2	COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3957.8	Standard polar	33892256
Sulfametopyrazine,3TBDMS,isomer #1	COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3232.3	Semi standard non polar	33892256
Sulfametopyrazine,3TBDMS,isomer #1	COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3451.9	Standard non polar	33892256
Sulfametopyrazine,3TBDMS,isomer #1	COC1=NC=CN=C1N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3560.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfametopyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05ec-8950000000-e07820181c0d509b6744	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfametopyrazine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfametopyrazine 10V, Positive-QTOF	splash10-001i-0390000000-901e323a546e976e468e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfametopyrazine 20V, Positive-QTOF	splash10-0a4i-1930000000-14c0572c4c8b184323b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfametopyrazine 40V, Positive-QTOF	splash10-0006-9100000000-a03460e59f372cc5cc79	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfametopyrazine 10V, Negative-QTOF	splash10-004i-0090000000-f18189296f030c2007f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfametopyrazine 20V, Negative-QTOF	splash10-0a6r-9270000000-122f98f83af5be9e3a36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfametopyrazine 40V, Negative-QTOF	splash10-0006-9510000000-25323d1786b9b00afa09	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfametopyrazine 10V, Positive-QTOF	splash10-001i-0090000000-3b2c30b44d481a3733fb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfametopyrazine 20V, Positive-QTOF	splash10-0a4i-2900000000-89fba7919d1854eb9b3f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfametopyrazine 40V, Positive-QTOF	splash10-014l-9300000000-3fc5a487e85969c7a3df	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfametopyrazine 10V, Negative-QTOF	splash10-004i-0290000000-941b74251f448ece145c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfametopyrazine 20V, Negative-QTOF	splash10-0a4i-2900000000-81a3b923ab8ab3af7890	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfametopyrazine 40V, Negative-QTOF	splash10-052f-6900000000-10bd0c8b52e73e20a8d8	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 DB00664	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00664	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00664

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8695

KEGG Compound ID

C12616

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulfalene

METLIN ID

Not Available

PubChem Compound

9047

PDB ID

Not Available

ChEBI ID

1049710

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 Sulfametopyrazine (HMDB0014802)

MOL for HMDB0014802 (Sulfametopyrazine)

3D MOL for HMDB0014802 (Sulfametopyrazine)

3D SDF for HMDB0014802 (Sulfametopyrazine)

3D-SDF for HMDB0014802 (Sulfametopyrazine)

PDB for HMDB0014802 (Sulfametopyrazine)

3D PDB for HMDB0014802 (Sulfametopyrazine)

SMILES for HMDB0014802 (Sulfametopyrazine)

INCHI for HMDB0014802 (Sulfametopyrazine)

Structure for HMDB0014802 (Sulfametopyrazine)

3D Structure for HMDB0014802 (Sulfametopyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra