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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

HMDB0015412

Secondary Accession Numbers

HMDB15412

Metabolite Identification

Common Name

Sulfacytine

Description

Sulfacytine is a short-acting sulfonamide. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Sulfacytine is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of of dihydrofolic acid by preventing the condensation of the pteridine with para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. 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

HMDB0015412
     RDKit          3D
Sulfacytine
 34 35  0  0  0  0  0  0  0  0999 V2000
    5.0385   -0.7014    1.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8059   -0.0064    1.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8139    0.2171    0.7205 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8514    1.3770    0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9210    1.6516   -0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078    0.7367   -1.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0315    1.0430   -2.2671 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2845   -0.0523   -2.6472 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.7264   -1.3660   -3.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0965    0.5088   -3.7740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3212   -0.3166   -1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1080   -1.3677   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9610   -1.5427    0.6848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0188   -0.7016    0.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8795   -0.8960    2.0697 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2237    0.3485    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3911    0.5337   -1.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9117   -0.3808   -0.5407 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8213   -0.6262    0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7726   -1.7097    1.0539 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689   -1.7454    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5192   -0.0881    0.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7707   -0.7240    2.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1281    0.9787    2.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4204   -0.5742    2.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6274    2.0870    0.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9524    2.5819   -1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0581    1.9543   -2.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2965   -2.0667   -0.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8138   -2.3701    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7728   -1.4313    1.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6676   -0.5385    3.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0570    1.0241    0.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5393    1.3534   -1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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 19  1  0
 19 20  2  0
 19  3  1  0
 17 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
M  END

1298
  Mrv0541 02231215222D          

 20 21  0  0  0  0            999 V2000
    3.7935    0.9818    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    0.2673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    1.6962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.9058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.9058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.6318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.1433    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  9  1  0  0  0  0
  4 16  2  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  5 16  1  0  0  0  0
  6 10  1  0  0  0  0
  7 10  2  0  0  0  0
  7 16  1  0  0  0  0
  8 19  1  0  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 10 13  1  0  0  0  0
 11 20  1  0  0  0  0
 12 13  2  0  0  0  0
 14 17  1  0  0  0  0
 15 18  2  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015412

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N4O3S/c1-2-16-8-7-11(14-12(16)17)15-20(18,19)10-5-3-9(13)4-6-10/h3-8H,2,13H2,1H3,(H,14,15,17)

> <INCHI_KEY>
SIBQAECNSSQUOD-UHFFFAOYSA-N

> <FORMULA>
C12H14N4O3S

> <MOLECULAR_WEIGHT>
294.33

> <EXACT_MASS>
294.078661024

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.427958370417702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-N-(1-ethyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzene-1-sulfonamide

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
0.05499847633333288

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.552587798907739

> <JCHEM_PKA_STRONGEST_BASIC>
2.1655696702755893

> <JCHEM_POLAR_SURFACE_AREA>
104.86

> <JCHEM_REFRACTIVITY>
75.488

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfacytine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015412
     RDKit          3D
Sulfacytine
 34 35  0  0  0  0  0  0  0  0999 V2000
    5.0385   -0.7014    1.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8059   -0.0064    1.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8139    0.2171    0.7205 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8514    1.3770    0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9210    1.6516   -0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078    0.7367   -1.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0315    1.0430   -2.2671 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2845   -0.0523   -2.6472 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.7264   -1.3660   -3.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0965    0.5088   -3.7740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3212   -0.3166   -1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1080   -1.3677   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9610   -1.5427    0.6848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0188   -0.7016    0.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8795   -0.8960    2.0697 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2237    0.3485    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3911    0.5337   -1.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9117   -0.3808   -0.5407 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8213   -0.6262    0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7726   -1.7097    1.0539 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689   -1.7454    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5192   -0.0881    0.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7707   -0.7240    2.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1281    0.9787    2.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4204   -0.5742    2.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6274    2.0870    0.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9524    2.5819   -1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0581    1.9543   -2.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2965   -2.0667   -0.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8138   -2.3701    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7728   -1.4313    1.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6676   -0.5385    3.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0570    1.0241    0.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5393    1.3534   -1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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 19  1  0
 19 20  2  0
 19  3  1  0
 17 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1298                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       7.081   1.833   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       7.851   0.499   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.311   3.166   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080  -3.557   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.748  -3.557   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       5.748   1.063   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       4.414  -1.247   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      12.416   4.913   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       8.415   2.603   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -0.477   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -5.097   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -2.787   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -1.247   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748   1.833   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   4.143   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -2.787   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082   2.603   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748   4.913   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082   4.143   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.081  -5.867   0.000  0.00  0.00           C+0
CONECT    1    2    3    6    9                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   16                                                            
CONECT    5   11   12   16                                                  
CONECT    6    1   10                                                       
CONECT    7   10   16                                                       
CONECT    8   19                                                            
CONECT    9    1   14   15                                                  
CONECT   10    6    7   13                                                  
CONECT   11    5   20                                                       
CONECT   12    5   13                                                       
CONECT   13   10   12                                                       
CONECT   14    9   17                                                       
CONECT   15    9   18                                                       
CONECT   16    4    5    7                                                  
CONECT   17   14   19                                                       
CONECT   18   15   19                                                       
CONECT   19    8   17   18                                                  
CONECT   20   11                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0015412
HETATM    1  C1  UNL     1       5.038  -0.701   1.210  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.806  -0.006   1.721  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.814   0.217   0.720  1.00  0.00           N  
HETATM    4  C3  UNL     1       2.851   1.377   0.010  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.921   1.652  -0.969  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.908   0.737  -1.259  1.00  0.00           C  
HETATM    7  N2  UNL     1      -0.031   1.043  -2.267  1.00  0.00           N  
HETATM    8  S1  UNL     1      -1.285  -0.052  -2.647  1.00  0.00           S  
HETATM    9  O1  UNL     1      -0.726  -1.366  -3.116  1.00  0.00           O  
HETATM   10  O2  UNL     1      -2.096   0.509  -3.774  1.00  0.00           O  
HETATM   11  C6  UNL     1      -2.321  -0.317  -1.272  1.00  0.00           C  
HETATM   12  C7  UNL     1      -2.108  -1.368  -0.411  1.00  0.00           C  
HETATM   13  C8  UNL     1      -2.961  -1.543   0.685  1.00  0.00           C  
HETATM   14  C9  UNL     1      -4.019  -0.702   0.946  1.00  0.00           C  
HETATM   15  N3  UNL     1      -4.879  -0.896   2.070  1.00  0.00           N  
HETATM   16  C10 UNL     1      -4.224   0.349   0.076  1.00  0.00           C  
HETATM   17  C11 UNL     1      -3.391   0.534  -1.008  1.00  0.00           C  
HETATM   18  N4  UNL     1       0.912  -0.381  -0.541  1.00  0.00           N  
HETATM   19  C12 UNL     1       1.821  -0.626   0.402  1.00  0.00           C  
HETATM   20  O3  UNL     1       1.773  -1.710   1.054  1.00  0.00           O  
HETATM   21  H1  UNL     1       4.869  -1.745   0.920  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.519  -0.088   0.426  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.771  -0.724   2.062  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.128   0.979   2.118  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.420  -0.574   2.605  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.627   2.087   0.227  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.952   2.582  -1.538  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.058   1.954  -2.774  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.296  -2.067  -0.562  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.814  -2.370   1.385  1.00  0.00           H  
HETATM   31  H11 UNL     1      -5.773  -1.431   1.917  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.668  -0.539   3.018  1.00  0.00           H  
HETATM   33  H13 UNL     1      -5.057   1.024   0.268  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.539   1.353  -1.700  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   19
CONECT    4    5    5   26
CONECT    5    6   27
CONECT    6    7   18   18
CONECT    7    8   28
CONECT    8    9    9   10   10
CONECT    8   11
CONECT   11   12   12   17
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15   16
CONECT   15   31   32
CONECT   16   17   17   33
CONECT   17   34
CONECT   18   19
CONECT   19   20   20
END

HMDB0015412
     RDKit          3D
Sulfacytine
 34 35  0  0  0  0  0  0  0  0999 V2000
    5.0385   -0.7014    1.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8059   -0.0064    1.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8139    0.2171    0.7205 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8514    1.3770    0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9210    1.6516   -0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078    0.7367   -1.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0315    1.0430   -2.2671 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2845   -0.0523   -2.6472 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.7264   -1.3660   -3.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0965    0.5088   -3.7740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3212   -0.3166   -1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1080   -1.3677   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9610   -1.5427    0.6848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0188   -0.7016    0.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8795   -0.8960    2.0697 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2237    0.3485    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3911    0.5337   -1.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9117   -0.3808   -0.5407 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8213   -0.6262    0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7726   -1.7097    1.0539 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689   -1.7454    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5192   -0.0881    0.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7707   -0.7240    2.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1281    0.9787    2.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4204   -0.5742    2.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6274    2.0870    0.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9524    2.5819   -1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0581    1.9543   -2.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2965   -2.0667   -0.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8138   -2.3701    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7728   -1.4313    1.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6676   -0.5385    3.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0570    1.0241    0.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5393    1.3534   -1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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 19  1  0
 19 20  2  0
 19  3  1  0
 17 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Renoquid	Kegg
Sulphacytine	Generator
1-Ethyl N4-sulfanilylcytosin	HMDB
1-Ethyl-N-sulfanilylcytosine	HMDB
N-Sulfanilyl-L-ethylcytosine	HMDB
N(1)-(1-Ethyl-1,2-dihydro-2-oxo-4-pyrimidinyl)sulfanilamide	HMDB

Chemical Formula

C₁₂H₁₄N₄O₃S

Average Molecular Weight

294.33

Monoisotopic Molecular Weight

294.078661024

IUPAC Name

4-amino-N-(1-ethyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzene-1-sulfonamide

Traditional Name

sulfacytine

CAS Registry Number

17784-12-2

SMILES

CCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O

InChI Identifier

InChI=1S/C12H14N4O3S/c1-2-16-8-7-11(14-12(16)17)15-20(18,19)10-5-3-9(13)4-6-10/h3-8H,2,13H2,1H3,(H,14,15,17)

InChI Key

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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: HMDB0015412)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	166.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.47 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.47 g/L	ALOGPS
logP	0.51	ALOGPS
logP	0.055	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	10.55	ChemAxon
pKa (Strongest Basic)	2.17	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	104.86 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.49 m³·mol⁻¹	ChemAxon
Polarizability	29.43 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]+	168.017	31661259
DarkChem	[M-H]-	169.01	31661259
DeepCCS	[M+H]+	167.83	30932474
DeepCCS	[M-H]-	165.472	30932474
DeepCCS	[M-2H]-	198.358	30932474
DeepCCS	[M+Na]+	173.923	30932474
AllCCS	[M+H]+	167.0	32859911
AllCCS	[M+H-H2O]+	163.5	32859911
AllCCS	[M+NH4]+	170.2	32859911
AllCCS	[M+Na]+	171.1	32859911
AllCCS	[M-H]-	164.5	32859911
AllCCS	[M+Na-2H]-	164.4	32859911
AllCCS	[M+HCOO]-	164.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sulfacytine	CCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O	4573.6	Standard polar	33892256
Sulfacytine	CCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O	2946.3	Standard non polar	33892256
Sulfacytine	CCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O	3106.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sulfacytine,1TMS,isomer #1	CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O	3095.0	Semi standard non polar	33892256
Sulfacytine,1TMS,isomer #1	CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O	2839.4	Standard non polar	33892256
Sulfacytine,1TMS,isomer #1	CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O	4028.7	Standard polar	33892256
Sulfacytine,1TMS,isomer #2	CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O	2793.4	Semi standard non polar	33892256
Sulfacytine,1TMS,isomer #2	CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O	2740.2	Standard non polar	33892256
Sulfacytine,1TMS,isomer #2	CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O	4189.5	Standard polar	33892256
Sulfacytine,2TMS,isomer #1	CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O	2851.7	Semi standard non polar	33892256
Sulfacytine,2TMS,isomer #1	CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O	2872.8	Standard non polar	33892256
Sulfacytine,2TMS,isomer #1	CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=NC1=O	3672.0	Standard polar	33892256
Sulfacytine,2TMS,isomer #2	CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O	2865.2	Semi standard non polar	33892256
Sulfacytine,2TMS,isomer #2	CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O	2898.6	Standard non polar	33892256
Sulfacytine,2TMS,isomer #2	CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O	3775.2	Standard polar	33892256
Sulfacytine,3TMS,isomer #1	CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O	2735.0	Semi standard non polar	33892256
Sulfacytine,3TMS,isomer #1	CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O	2957.1	Standard non polar	33892256
Sulfacytine,3TMS,isomer #1	CCN1C=CC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=NC1=O	3475.2	Standard polar	33892256
Sulfacytine,1TBDMS,isomer #1	CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O	3341.2	Semi standard non polar	33892256
Sulfacytine,1TBDMS,isomer #1	CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O	3047.6	Standard non polar	33892256
Sulfacytine,1TBDMS,isomer #1	CCN1C=CC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O	4033.0	Standard polar	33892256
Sulfacytine,1TBDMS,isomer #2	CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O	3094.6	Semi standard non polar	33892256
Sulfacytine,1TBDMS,isomer #2	CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O	2971.0	Standard non polar	33892256
Sulfacytine,1TBDMS,isomer #2	CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=NC1=O	4175.3	Standard polar	33892256
Sulfacytine,2TBDMS,isomer #1	CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O	3319.1	Semi standard non polar	33892256
Sulfacytine,2TBDMS,isomer #1	CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O	3318.1	Standard non polar	33892256
Sulfacytine,2TBDMS,isomer #1	CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=NC1=O	3723.9	Standard polar	33892256
Sulfacytine,2TBDMS,isomer #2	CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O	3392.4	Semi standard non polar	33892256
Sulfacytine,2TBDMS,isomer #2	CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O	3330.4	Standard non polar	33892256
Sulfacytine,2TBDMS,isomer #2	CCN1C=CC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O	3770.4	Standard polar	33892256
Sulfacytine,3TBDMS,isomer #1	CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O	3468.3	Semi standard non polar	33892256
Sulfacytine,3TBDMS,isomer #1	CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O	3615.8	Standard non polar	33892256
Sulfacytine,3TBDMS,isomer #1	CCN1C=CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NC1=O	3610.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfacytine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0699-5970000000-fcf781e9c8d92fac41fe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfacytine 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 - Sulfacytine 10V, Positive-QTOF	splash10-002b-0490000000-f5ef4a3fc969278d52f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfacytine 20V, Positive-QTOF	splash10-0ab9-1930000000-cca50de9df755740762c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfacytine 40V, Positive-QTOF	splash10-0gb9-9100000000-0e0f88d63239781bb3dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfacytine 10V, Negative-QTOF	splash10-0006-0190000000-5678559deb4df7cd70e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfacytine 20V, Negative-QTOF	splash10-0zml-1590000000-f8b5e6818df98f145ac8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfacytine 40V, Negative-QTOF	splash10-05bf-9710000000-fe4bdffade8dc1239d0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfacytine 10V, Positive-QTOF	splash10-052b-0790000000-858e661c23fea2a281ef	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfacytine 20V, Positive-QTOF	splash10-0005-1950000000-8efb821459dc738d0bc6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfacytine 40V, Positive-QTOF	splash10-0006-9310000000-af522fa67546c379ca39	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfacytine 10V, Negative-QTOF	splash10-0006-0290000000-14fefa164bb613784c58	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfacytine 20V, Negative-QTOF	splash10-00dm-0920000000-252f3b6dbf3bb165dace	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfacytine 40V, Negative-QTOF	splash10-052f-6900000000-bc74a22245fbb377bce2	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 DB01298	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01298	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01298

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5131

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulfacytine

METLIN ID

Not Available

PubChem Compound

5322

PDB ID

Not Available

ChEBI ID

775007

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 Sulfacytine (HMDB0015412)

MOL for HMDB0015412 (Sulfacytine)

3D MOL for HMDB0015412 (Sulfacytine)

3D SDF for HMDB0015412 (Sulfacytine)

3D-SDF for HMDB0015412 (Sulfacytine)

PDB for HMDB0015412 (Sulfacytine)

3D PDB for HMDB0015412 (Sulfacytine)

SMILES for HMDB0015412 (Sulfacytine)

INCHI for HMDB0015412 (Sulfacytine)

Structure for HMDB0015412 (Sulfacytine)

3D Structure for HMDB0015412 (Sulfacytine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra