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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:23:32 UTC

Update Date

2021-09-26 23:10:36 UTC

HMDB ID

HMDB0255611

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Nimesulide

Description

Nimesulide belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. An aromatic ether having phenyl and 2-methylsulfonamido-5-nitrophenyl as the two aryl groups. Nimesulide is a drug which is used for the treatment of acute pain, the symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults above 12 years old. Nimesulide is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Nimesulide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Nimesulide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0255611
     RDKit          3D
Nimesulide
 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.3501   -1.5660    1.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5570   -1.9869   -0.3025 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.7466   -3.4562   -0.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3074   -1.2612   -1.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8948   -1.6043   -0.3050 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4310   -0.2714   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2877    0.8011    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8009    2.0817    0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4404    2.3650    0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0560    3.6801    0.3046 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.2773    3.8692    0.2912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8085    4.7230    0.4631 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.4095    1.2952   -0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0778    0.0149   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7900   -1.0330   -0.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1681   -0.7995   -0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985   -0.5363   -1.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1564   -0.3045   -1.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9329   -0.3243   -0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2752   -0.5905    0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9210   -0.8238    0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6025   -1.2164    1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8230   -2.4753    1.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1758   -0.8370    1.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1809   -2.3543   -0.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3471    0.6166    0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4664    2.9396    0.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    1.4750   -0.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2041   -0.5142   -2.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6173   -0.1025   -2.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9923   -0.1473   -0.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8311   -0.6194    1.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3818   -1.0371    1.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 14  6  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 13 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
M  CHG  2  10   1  12  -1
M  END

[NO NAME]
  Mrv0541 04301222212D          
Created with ChemWriter - http://chemwriter.com
 21 22  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433   -2.0625    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.4290   -1.6500    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.7144   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
 16  2  2  0  0  0  0
  9  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  1  1  0  0  0  0
  6  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5 12  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 12 10  1  0  0  0  0
 10 11  2  0  0  0  0
 16 11  1  0  0  0  0
 12 14  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  2  0  0  0  0
 18 21  1  0  0  0  0
 18 19  2  0  0  0  0
M  CHG  2  13  -1  14   1
M  END
> <DATABASE_ID>
HMDB0255611

> <DATABASE_NAME>
hmdb

> <SMILES>
CS(=O)(=O)NC1=C(OC2=CC=CC=C2)C=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H12N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h2-9,14H,1H3

> <INCHI_KEY>
HYWYRSMBCFDLJT-UHFFFAOYSA-N

> <FORMULA>
C13H12N2O5S

> <MOLECULAR_WEIGHT>
308.31

> <EXACT_MASS>
308.046692194

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.872423548287472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(4-nitro-2-phenoxyphenyl)methanesulfonamide

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
1.7866563706666665

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.855871203275389

> <JCHEM_PKA_STRONGEST_BASIC>
-8.913623712767949

> <JCHEM_POLAR_SURFACE_AREA>
101.22

> <JCHEM_REFRACTIVITY>
76.30669999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nimesulide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255611
     RDKit          3D
Nimesulide
 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.3501   -1.5660    1.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5570   -1.9869   -0.3025 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.7466   -3.4562   -0.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3074   -1.2612   -1.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8948   -1.6043   -0.3050 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4310   -0.2714   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2877    0.8011    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8009    2.0817    0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4404    2.3650    0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0560    3.6801    0.3046 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.2773    3.8692    0.2912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8085    4.7230    0.4631 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.4095    1.2952   -0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0778    0.0149   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7900   -1.0330   -0.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1681   -0.7995   -0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985   -0.5363   -1.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1564   -0.3045   -1.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9329   -0.3243   -0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2752   -0.5905    0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9210   -0.8238    0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6025   -1.2164    1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8230   -2.4753    1.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1758   -0.8370    1.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1809   -2.3543   -0.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3471    0.6166    0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4664    2.9396    0.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    1.4750   -0.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2041   -0.5142   -2.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6173   -0.1025   -2.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9923   -0.1473   -0.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8311   -0.6194    1.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3818   -1.0371    1.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 14  6  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 13 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
M  CHG  2  10   1  12  -1
M  END

HEADER    PROTEIN                                 30-APR-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-APR-12         0                                  
HETATM    1  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O-1
HETATM   14  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+1
HETATM   15  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.667   3.080   0.000  0.00  0.00           N+0
HETATM   18  S   UNK     0       4.001   3.850   0.000  0.00  0.00           S+0
HETATM   19  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1   16    5                                                  
CONECT    3    9    4                                                       
CONECT    4    3    1    6                                                  
CONECT    5    2   12                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    3    8                                                       
CONECT   10   12   11                                                       
CONECT   11   10   16                                                       
CONECT   12    5   10   14                                                  
CONECT   13   14                                                            
CONECT   14   12   13   15                                                  
CONECT   15   14                                                            
CONECT   16    2   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   20   21   19                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0255611
HETATM    1  C1  UNL     1      -4.350  -1.566   1.228  1.00  0.00           C  
HETATM    2  S1  UNL     1      -3.557  -1.987  -0.302  1.00  0.00           S  
HETATM    3  O1  UNL     1      -3.747  -3.456  -0.550  1.00  0.00           O  
HETATM    4  O2  UNL     1      -4.307  -1.261  -1.399  1.00  0.00           O  
HETATM    5  N1  UNL     1      -1.895  -1.604  -0.305  1.00  0.00           N  
HETATM    6  C2  UNL     1      -1.431  -0.271  -0.150  1.00  0.00           C  
HETATM    7  C3  UNL     1      -2.288   0.801   0.012  1.00  0.00           C  
HETATM    8  C4  UNL     1      -1.801   2.082   0.159  1.00  0.00           C  
HETATM    9  C5  UNL     1      -0.440   2.365   0.153  1.00  0.00           C  
HETATM   10  N2  UNL     1       0.056   3.680   0.305  1.00  0.00           N1+
HETATM   11  O3  UNL     1       1.277   3.869   0.291  1.00  0.00           O  
HETATM   12  O4  UNL     1      -0.808   4.723   0.463  1.00  0.00           O1-
HETATM   13  C6  UNL     1       0.409   1.295  -0.008  1.00  0.00           C  
HETATM   14  C7  UNL     1      -0.078   0.015  -0.155  1.00  0.00           C  
HETATM   15  O5  UNL     1       0.790  -1.033  -0.315  1.00  0.00           O  
HETATM   16  C8  UNL     1       2.168  -0.799  -0.327  1.00  0.00           C  
HETATM   17  C9  UNL     1       2.798  -0.536  -1.519  1.00  0.00           C  
HETATM   18  C10 UNL     1       4.156  -0.304  -1.544  1.00  0.00           C  
HETATM   19  C11 UNL     1       4.933  -0.324  -0.402  1.00  0.00           C  
HETATM   20  C12 UNL     1       4.275  -0.591   0.779  1.00  0.00           C  
HETATM   21  C13 UNL     1       2.921  -0.824   0.820  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.603  -1.216   1.977  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.823  -2.475   1.696  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.176  -0.837   1.095  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.181  -2.354  -0.422  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.347   0.617   0.021  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.466   2.940   0.288  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.486   1.475  -0.018  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.204  -0.514  -2.446  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.617  -0.102  -2.489  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.992  -0.147  -0.392  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.831  -0.619   1.708  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.382  -1.037   1.750  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    4    4
CONECT    2    5
CONECT    5    6   25
CONECT    6    7    7   14
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10   13
CONECT   10   11   11   12
CONECT   13   14   14   28
CONECT   14   15
CONECT   15   16
CONECT   16   17   17   21
CONECT   17   18   29
CONECT   18   19   19   30
CONECT   19   20   31
CONECT   20   21   21   32
CONECT   21   33
END

HMDB0255611
     RDKit          3D
Nimesulide
 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.3501   -1.5660    1.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5570   -1.9869   -0.3025 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.7466   -3.4562   -0.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3074   -1.2612   -1.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8948   -1.6043   -0.3050 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4310   -0.2714   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2877    0.8011    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8009    2.0817    0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4404    2.3650    0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0560    3.6801    0.3046 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.2773    3.8692    0.2912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8085    4.7230    0.4631 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.4095    1.2952   -0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0778    0.0149   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7900   -1.0330   -0.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1681   -0.7995   -0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985   -0.5363   -1.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1564   -0.3045   -1.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9329   -0.3243   -0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2752   -0.5905    0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9210   -0.8238    0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6025   -1.2164    1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8230   -2.4753    1.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1758   -0.8370    1.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1809   -2.3543   -0.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3471    0.6166    0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4664    2.9396    0.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    1.4750   -0.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2041   -0.5142   -2.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6173   -0.1025   -2.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9923   -0.1473   -0.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8311   -0.6194    1.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3818   -1.0371    1.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 14  6  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 13 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
M  CHG  2  10   1  12  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4'-Nitro-2'-phenoxymethanesulfonanilide	ChEBI
4-NITRO-2-phenoxymethanesulfonanilide	ChEBI
4'-Nitro-2'-phenoxymethanesulphonanilide	Generator
4-NITRO-2-phenoxymethanesulphonanilide	Generator
Antifloxil	MeSH
Aulin	MeSH
Eskaflam	MeSH
Mesulid	MeSH
Nexen	MeSH
Redaflam	MeSH
Guaxan	MeSH
Nimesil	MeSH
Lizepat	MeSH

Chemical Formula

C₁₃H₁₂N₂O₅S

Average Molecular Weight

308.31

Monoisotopic Molecular Weight

308.046692194

IUPAC Name

N-(4-nitro-2-phenoxyphenyl)methanesulfonamide

Traditional Name

nimesulide

CAS Registry Number

Not Available

SMILES

CS(=O)(=O)NC1=C(OC2=CC=CC=C2)C=C(C=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C13H12N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h2-9,14H,1H3

InChI Key

HYWYRSMBCFDLJT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

Alternative Parents

Substituents

Diphenylether
Diaryl ether
Sulfanilide
Nitrobenzene
Phenoxy compound
Nitroaromatic compound
Phenol ether
Organic sulfonic acid amide
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
C-nitro compound
Organic nitro compound
Organic 1,3-dipolar compound
Ether
Organic oxoazanium
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic zwitterion
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:44445 )
aromatic ether (CHEBI:44445 )
sulfonamide (CHEBI:44445 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0255611)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.56	ALOGPS
logP	1.79	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	6.86	ChemAxon
pKa (Strongest Basic)	-8.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	101.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.31 m³·mol⁻¹	ChemAxon
Polarizability	28.87 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
DeepCCS	[M+H]+	157.531	30932474
DeepCCS	[M-H]-	155.173	30932474
DeepCCS	[M-2H]-	188.349	30932474
DeepCCS	[M+Na]+	164.241	30932474
AllCCS	[M+H]+	167.3	32859911
AllCCS	[M+H-H2O]+	163.9	32859911
AllCCS	[M+NH4]+	170.4	32859911
AllCCS	[M+Na]+	171.3	32859911
AllCCS	[M-H]-	162.6	32859911
AllCCS	[M+Na-2H]-	162.0	32859911
AllCCS	[M+HCOO]-	161.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	14.0053 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.95 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2120.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	418.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	168.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	231.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	184.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	530.7 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	629.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	129.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1256.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	459.7 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	1306.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	383.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	423.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	366.9 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	33.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nimesulide	CS(=O)(=O)NC1=C(OC2=CC=CC=C2)C=C(C=C1)[N+]([O-])=O	4258.6	Standard polar	33892256
Nimesulide	CS(=O)(=O)NC1=C(OC2=CC=CC=C2)C=C(C=C1)[N+]([O-])=O	2650.4	Standard non polar	33892256
Nimesulide	CS(=O)(=O)NC1=C(OC2=CC=CC=C2)C=C(C=C1)[N+]([O-])=O	2618.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nimesulide,1TMS,isomer #1	C[Si](C)(C)N(C1=CC=C([N+](=O)[O-])C=C1OC1=CC=CC=C1)S(C)(=O)=O	2532.0	Semi standard non polar	33892256
Nimesulide,1TMS,isomer #1	C[Si](C)(C)N(C1=CC=C([N+](=O)[O-])C=C1OC1=CC=CC=C1)S(C)(=O)=O	2588.7	Standard non polar	33892256
Nimesulide,1TMS,isomer #1	C[Si](C)(C)N(C1=CC=C([N+](=O)[O-])C=C1OC1=CC=CC=C1)S(C)(=O)=O	3556.3	Standard polar	33892256
Nimesulide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C([N+](=O)[O-])C=C1OC1=CC=CC=C1)S(C)(=O)=O	2794.9	Semi standard non polar	33892256
Nimesulide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C([N+](=O)[O-])C=C1OC1=CC=CC=C1)S(C)(=O)=O	2825.2	Standard non polar	33892256
Nimesulide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C([N+](=O)[O-])C=C1OC1=CC=CC=C1)S(C)(=O)=O	3569.1	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04743

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nimesulide

METLIN ID

Not Available

PubChem Compound

4495

PDB ID

Not Available

ChEBI ID

44445

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Nimesulide (HMDB0255611)

MOL for HMDB0255611 (Nimesulide)

3D MOL for HMDB0255611 (Nimesulide)

3D SDF for HMDB0255611 (Nimesulide)

3D-SDF for HMDB0255611 (Nimesulide)

PDB for HMDB0255611 (Nimesulide)

3D PDB for HMDB0255611 (Nimesulide)

SMILES for HMDB0255611 (Nimesulide)

INCHI for HMDB0255611 (Nimesulide)

Structure for HMDB0255611 (Nimesulide)

3D Structure for HMDB0255611 (Nimesulide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized