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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:50:18 UTC

Update Date

2021-09-26 23:08:32 UTC

HMDB ID

HMDB0254502

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Metamizol

Description

metamizole, also known as sulpyrine or dolemicin, belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group. metamizole is an extremely weak basic (essentially neutral) compound (based on its pKa). A pyrazole that is antiipyrine substituted at C-4 by a methyl(sulfomethyl)amino group, the sodium salt of which, metamizole sodium, was widely used as a powerful analgesic and antipyretic, but withdrawn from many markets from the 1970s due to a risk of causing risk of causing agranulocytosis. This compound has been identified in human blood as reported by (PMID: 31557052 ). Metamizol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Metamizol 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

HMDB0254502
     RDKit          3D
Metamizol
 38 39  0  0  0  0  0  0  0  0999 V2000
   -1.1837   -2.6546    0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3775   -1.4174    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9482   -0.1734   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3115    0.2133   -0.1215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9967    0.2266   -1.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9701    0.5820    1.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6523    1.0360    0.8783 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.5007   -0.1398    0.4748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1793    1.4737    2.2389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450    2.3423   -0.1447 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157    0.6936   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0533    1.9419   -0.3736 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2745   -0.0206   -0.0885 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5757    0.5330   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839    1.3171   -1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2748    1.8532   -1.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1252    1.5588   -0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7557    0.7754    0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4631    0.2732    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9782   -1.2965    0.0972 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051   -2.4000    0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8263   -2.7730   -0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5555   -3.5392    0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9143   -2.4929    1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -0.3884   -2.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9644    1.2735   -1.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0291   -0.1690   -1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4323    1.4772    1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9368   -0.2351    1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5185    2.1017   -0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3168    1.5351   -2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5971    2.4717   -2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1499    1.9477   -0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4251    0.5482    1.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1900   -0.3450    1.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9428   -2.7098    1.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099   -2.1315   -0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800   -3.2890   -0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
  3 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13 20  1  0
 20 21  1  0
 20  2  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
 10 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  1  0
 21 37  1  0
 21 38  1  0
M  END

  Mrv1533004241521172D          

 21 22  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -3.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -1.4675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3381   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796   -2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5642   -1.7646    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3489   -1.5096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8192   -2.5492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3093   -0.9800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  2  0  0  0  0
 18 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254502

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(CS(O)(=O)=O)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H17N3O4S/c1-10-12(14(2)9-21(18,19)20)13(17)16(15(10)3)11-7-5-4-6-8-11/h4-8H,9H2,1-3H3,(H,18,19,20)

> <INCHI_KEY>
LVWZTYCIRDMTEY-UHFFFAOYSA-N

> <FORMULA>
C13H17N3O4S

> <MOLECULAR_WEIGHT>
311.36

> <EXACT_MASS>
311.093977213

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.412013890461367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(methyl)amino]methanesulfonic acid

> <ALOGPS_LOGP>
-0.40

> <JCHEM_LOGP>
-0.8187838750869002

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.312089573407697

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.4195522440436088

> <JCHEM_PKA_STRONGEST_BASIC>
-0.537233155071097

> <JCHEM_POLAR_SURFACE_AREA>
81.16000000000001

> <JCHEM_REFRACTIVITY>
80.0412

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
metamizole

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254502
     RDKit          3D
Metamizol
 38 39  0  0  0  0  0  0  0  0999 V2000
   -1.1837   -2.6546    0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3775   -1.4174    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9482   -0.1734   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3115    0.2133   -0.1215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9967    0.2266   -1.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9701    0.5820    1.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6523    1.0360    0.8783 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.5007   -0.1398    0.4748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1793    1.4737    2.2389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450    2.3423   -0.1447 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157    0.6936   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0533    1.9419   -0.3736 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2745   -0.0206   -0.0885 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5757    0.5330   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839    1.3171   -1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2748    1.8532   -1.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1252    1.5588   -0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7557    0.7754    0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4631    0.2732    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9782   -1.2965    0.0972 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051   -2.4000    0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8263   -2.7730   -0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5555   -3.5392    0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9143   -2.4929    1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -0.3884   -2.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9644    1.2735   -1.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0291   -0.1690   -1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4323    1.4772    1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9368   -0.2351    1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5185    2.1017   -0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3168    1.5351   -2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5971    2.4717   -2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1499    1.9477   -0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4251    0.5482    1.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1900   -0.3450    1.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9428   -2.7098    1.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099   -2.1315   -0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800   -3.2890   -0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
  3 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13 20  1  0
 20 21  1  0
 20  2  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
 10 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  1  0
 21 37  1  0
 21 38  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.009  -5.926   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       0.564  -4.680   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       0.088  -3.215   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.285  -7.333   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.620  -8.578   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.152  -8.417   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.778  -7.011   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.873  -5.765   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.044  -2.739   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       4.364  -1.233   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.189  -3.770   0.000  0.00  0.00           C+0
HETATM   18  S   UNK     0       6.653  -3.294   0.000  0.00  0.00           S+0
HETATM   19  O   UNK     0       8.118  -2.818   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.129  -4.759   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.177  -1.829   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    9                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    3   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0254502
HETATM    1  C1  UNL     1      -1.184  -2.655   0.295  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.377  -1.417   0.115  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.948  -0.173  -0.066  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.311   0.213  -0.121  1.00  0.00           N  
HETATM    5  C4  UNL     1      -2.997   0.227  -1.394  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.970   0.582   1.101  1.00  0.00           C  
HETATM    7  S1  UNL     1      -4.652   1.036   0.878  1.00  0.00           S  
HETATM    8  O1  UNL     1      -5.501  -0.140   0.475  1.00  0.00           O  
HETATM    9  O2  UNL     1      -5.179   1.474   2.239  1.00  0.00           O  
HETATM   10  O3  UNL     1      -4.845   2.342  -0.145  1.00  0.00           O  
HETATM   11  C6  UNL     1       0.116   0.694  -0.192  1.00  0.00           C  
HETATM   12  O4  UNL     1       0.053   1.942  -0.374  1.00  0.00           O  
HETATM   13  N2  UNL     1       1.274  -0.021  -0.088  1.00  0.00           N  
HETATM   14  C7  UNL     1       2.576   0.533  -0.169  1.00  0.00           C  
HETATM   15  C8  UNL     1       2.984   1.317  -1.219  1.00  0.00           C  
HETATM   16  C9  UNL     1       4.275   1.853  -1.277  1.00  0.00           C  
HETATM   17  C10 UNL     1       5.125   1.559  -0.229  1.00  0.00           C  
HETATM   18  C11 UNL     1       4.756   0.775   0.845  1.00  0.00           C  
HETATM   19  C12 UNL     1       3.463   0.273   0.845  1.00  0.00           C  
HETATM   20  N3  UNL     1       0.978  -1.296   0.097  1.00  0.00           N  
HETATM   21  C13 UNL     1       1.905  -2.400   0.257  1.00  0.00           C  
HETATM   22  H1  UNL     1      -1.826  -2.773  -0.608  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.556  -3.539   0.443  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.914  -2.493   1.142  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.475  -0.388  -2.159  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.964   1.274  -1.762  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.029  -0.169  -1.340  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.432   1.477   1.501  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.937  -0.235   1.851  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.518   2.102  -0.847  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.317   1.535  -2.020  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.597   2.472  -2.105  1.00  0.00           H  
HETATM   33  H12 UNL     1       6.150   1.948  -0.214  1.00  0.00           H  
HETATM   34  H13 UNL     1       5.425   0.548   1.662  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.190  -0.345   1.704  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.943  -2.710   1.321  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.910  -2.132  -0.120  1.00  0.00           H  
HETATM   38  H17 UNL     1       1.580  -3.289  -0.323  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   20
CONECT    3    4   11
CONECT    4    5    6
CONECT    5   25   26   27
CONECT    6    7   28   29
CONECT    7    8    8    9    9
CONECT    7   10
CONECT   10   30
CONECT   11   12   12   13
CONECT   13   14   20
CONECT   14   15   15   19
CONECT   15   16   31
CONECT   16   17   17   32
CONECT   17   18   33
CONECT   18   19   19   34
CONECT   19   35
CONECT   20   21
CONECT   21   36   37   38
END

HMDB0254502
     RDKit          3D
Metamizol
 38 39  0  0  0  0  0  0  0  0999 V2000
   -1.1837   -2.6546    0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3775   -1.4174    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9482   -0.1734   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3115    0.2133   -0.1215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9967    0.2266   -1.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9701    0.5820    1.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6523    1.0360    0.8783 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.5007   -0.1398    0.4748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1793    1.4737    2.2389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450    2.3423   -0.1447 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157    0.6936   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0533    1.9419   -0.3736 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2745   -0.0206   -0.0885 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5757    0.5330   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839    1.3171   -1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2748    1.8532   -1.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1252    1.5588   -0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7557    0.7754    0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4631    0.2732    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9782   -1.2965    0.0972 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051   -2.4000    0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8263   -2.7730   -0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5555   -3.5392    0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9143   -2.4929    1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -0.3884   -2.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9644    1.2735   -1.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0291   -0.1690   -1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4323    1.4772    1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9368   -0.2351    1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5185    2.1017   -0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3168    1.5351   -2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5971    2.4717   -2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1499    1.9477   -0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4251    0.5482    1.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1900   -0.3450    1.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9428   -2.7098    1.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099   -2.1315   -0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800   -3.2890   -0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
  3 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13 20  1  0
 20 21  1  0
 20  2  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
 10 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  1  0
 21 37  1  0
 21 38  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(Antipyrinylmethylamino)methanesulfonic acid	ChEBI
[(2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methanesulfonic acid	ChEBI
Metamizol	ChEBI
Metamizolum	ChEBI
N-(2,3-Dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl)-N-methylaminomethanesulfonic acid	ChEBI
Methamizole	Kegg
Dolemicin	Kegg
(Antipyrinylmethylamino)methanesulfonate	Generator
(Antipyrinylmethylamino)methanesulphonate	Generator
(Antipyrinylmethylamino)methanesulphonic acid	Generator
[(2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methanesulfonate	Generator
[(2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methanesulphonate	Generator
[(2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methanesulphonic acid	Generator
N-(2,3-Dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl)-N-methylaminomethanesulfonate	Generator
N-(2,3-Dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl)-N-methylaminomethanesulphonate	Generator
N-(2,3-Dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl)-N-methylaminomethanesulphonic acid	Generator
Sulpyrine	MeSH
Noramidopyrine methanesulfonate	MeSH
Biopyrin	MeSH
Novalgetol	MeSH
Optalgin	MeSH
Dipyrone	MeSH
Methampyrone	MeSH
Metamizole sodium	MeSH
Novalgin	MeSH
Narone	MeSH
Noramidopyrine methanesulfonate sodium	MeSH
Novamidazophen	MeSH
Sulpyrin	MeSH
Normelubrine	MeSH
Dipyronium	MeSH
Algopyrin	MeSH
Novaminsulfone	MeSH
Pyralgin	MeSH
Analgin	MeSH

Chemical Formula

C₁₃H₁₇N₃O₄S

Average Molecular Weight

311.36

Monoisotopic Molecular Weight

311.093977213

IUPAC Name

[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(methyl)amino]methanesulfonic acid

Traditional Name

metamizole

CAS Registry Number

Not Available

SMILES

CN(CS(O)(=O)=O)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C13H17N3O4S/c1-10-12(14(2)9-21(18,19)20)13(17)16(15(10)3)11-7-5-4-6-8-11/h4-8H,9H2,1-3H3,(H,18,19,20)

InChI Key

LVWZTYCIRDMTEY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Pyrazoles

Direct Parent

Phenylpyrazoles

Alternative Parents

Substituents

Phenylpyrazole
Dialkylarylamine
Monocyclic benzene moiety
Pyrazolinone
Benzenoid
Organic sulfonic acid or derivatives
Heteroaromatic compound
Organosulfonic acid or derivatives
Vinylogous amide
Alkanesulfonic acid
Sulfonyl
Organosulfonic acid
Lactam
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazoles (CHEBI:62088 )
amino sulfonic acid (CHEBI:62088 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	-0.4	ALOGPS
logP	-0.82	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	-0.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	81.16 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.04 m³·mol⁻¹	ChemAxon
Polarizability	31.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	174.935	30932474
DeepCCS	[M-H]-	172.577	30932474
DeepCCS	[M-2H]-	206.361	30932474
DeepCCS	[M+Na]+	181.587	30932474
AllCCS	[M+H]+	170.0	32859911
AllCCS	[M+H-H2O]+	166.7	32859911
AllCCS	[M+NH4]+	173.0	32859911
AllCCS	[M+Na]+	173.8	32859911
AllCCS	[M-H]-	169.6	32859911
AllCCS	[M+Na-2H]-	169.5	32859911
AllCCS	[M+HCOO]-	169.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Metamizol	CN(CS(O)(=O)=O)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1	3537.9	Standard polar	33892256
Metamizol	CN(CS(O)(=O)=O)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1	1907.3	Standard non polar	33892256
Metamizol	CN(CS(O)(=O)=O)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1	2588.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Metamizol,1TMS,isomer #1	CC1=C(N(C)CS(=O)(=O)O[Si](C)(C)C)C(=O)N(C2=CC=CC=C2)N1C	2511.2	Semi standard non polar	33892256
Metamizol,1TMS,isomer #1	CC1=C(N(C)CS(=O)(=O)O[Si](C)(C)C)C(=O)N(C2=CC=CC=C2)N1C	2606.5	Standard non polar	33892256
Metamizol,1TMS,isomer #1	CC1=C(N(C)CS(=O)(=O)O[Si](C)(C)C)C(=O)N(C2=CC=CC=C2)N1C	3599.1	Standard polar	33892256
Metamizol,1TBDMS,isomer #1	CC1=C(N(C)CS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(=O)N(C2=CC=CC=C2)N1C	2753.8	Semi standard non polar	33892256
Metamizol,1TBDMS,isomer #1	CC1=C(N(C)CS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(=O)N(C2=CC=CC=C2)N1C	2899.0	Standard non polar	33892256
Metamizol,1TBDMS,isomer #1	CC1=C(N(C)CS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(=O)N(C2=CC=CC=C2)N1C	3558.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Metamizol GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-6790000000-5e2ad4e22902aef7ecfc	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metamizol 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 - Metamizol 10V, Negative-QTOF	splash10-03di-0009000000-b339baa1b70547a5a9fb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metamizol 20V, Negative-QTOF	splash10-03di-2139000000-c57009c68d162df03d38	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metamizol 40V, Negative-QTOF	splash10-001l-9330000000-ad5a8a6ce4427cb5e846	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metamizol 10V, Positive-QTOF	splash10-03xr-0089000000-3850df3ea112ab40ddea	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metamizol 20V, Positive-QTOF	splash10-014i-0191000000-4dd092ec01a63dd79a07	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metamizol 40V, Positive-QTOF	splash10-002f-9840000000-19dab0660005e3e81b6a	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

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

Not Available

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

Metamizole

METLIN ID

Not Available

PubChem Compound

3111

PDB ID

Not Available

ChEBI ID

62088

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 Metamizol (HMDB0254502)

MOL for HMDB0254502 (Metamizol)

3D MOL for HMDB0254502 (Metamizol)

3D SDF for HMDB0254502 (Metamizol)

3D-SDF for HMDB0254502 (Metamizol)

PDB for HMDB0254502 (Metamizol)

3D PDB for HMDB0254502 (Metamizol)

SMILES for HMDB0254502 (Metamizol)

INCHI for HMDB0254502 (Metamizol)

Structure for HMDB0254502 (Metamizol)

3D Structure for HMDB0254502 (Metamizol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra