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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:00 UTC

HMDB ID

HMDB0015493

Secondary Accession Numbers

HMDB15493

Metabolite Identification

Common Name

Aminophenazone

Description

Aminophenazone is only found in individuals that have used or taken this drug. It is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of agranulocytosis. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests. [PubChem]Aminophenazone is metabolized very slowly by normal newborn babies. In older infants, a higher amount of exhaled 13-CO2 is observed.

Structure

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

HMDB0015493
     RDKit          3D
Aminophenazone
 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.1489   -1.5640   -1.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1915   -0.7480   -0.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436    0.2218    0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8365    0.6752    0.4605 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4481    1.7699   -0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5415    0.0371    1.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3511    0.6876    0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124    1.5896    1.4712 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6819    0.0244    0.0159 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0746    0.2595    0.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898   -0.0634    1.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8002    0.1211    1.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6548    0.6399    1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2620    0.9695   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9429    0.7688   -0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497   -0.8253   -0.8261 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8962   -1.7399   -1.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1061   -1.0205   -1.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2848   -2.5759   -1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790   -1.6681   -2.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0888    2.3805    0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0862    1.4175   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6968    2.4636   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7957   -0.2237    2.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3336    0.6803    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0148   -0.8988    1.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7821   -0.4750    2.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1291   -0.1346    2.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6952    0.7828    1.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9460    1.3753   -0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5507    0.9996   -1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121   -2.6636   -1.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3425   -2.0069   -2.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8497   -1.2561   -2.0106 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
  3  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  1  0
 16  2  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
M  END

1424
  Mrv0541 02231215292D          

 17 18  0  0  1  0            999 V2000
    4.5542    0.1222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    0.3771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -0.1078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9996    1.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146    1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7696    0.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -0.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2047    1.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6640    2.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8201    1.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -1.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876   -1.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -2.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876   -2.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -2.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2 10  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  6  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  8 13  2  0  0  0  0
  8 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015493

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3

> <INCHI_KEY>
RMMXTBMQSGEXHJ-UHFFFAOYSA-N

> <FORMULA>
C13H17N3O

> <MOLECULAR_WEIGHT>
231.2936

> <EXACT_MASS>
231.137162181

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.86589988753915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(dimethylamino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one

> <ALOGPS_LOGP>
0.94

> <JCHEM_LOGP>
1.1505949156666666

> <ALOGPS_LOGS>
-1.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.4650629529248964

> <JCHEM_POLAR_SURFACE_AREA>
26.790000000000006

> <JCHEM_REFRACTIVITY>
70.11100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aminophenazone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015493
     RDKit          3D
Aminophenazone
 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.1489   -1.5640   -1.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1915   -0.7480   -0.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436    0.2218    0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8365    0.6752    0.4605 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4481    1.7699   -0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5415    0.0371    1.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3511    0.6876    0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124    1.5896    1.4712 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6819    0.0244    0.0159 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0746    0.2595    0.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898   -0.0634    1.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8002    0.1211    1.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6548    0.6399    1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2620    0.9695   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9429    0.7688   -0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497   -0.8253   -0.8261 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8962   -1.7399   -1.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1061   -1.0205   -1.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2848   -2.5759   -1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790   -1.6681   -2.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0888    2.3805    0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0862    1.4175   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6968    2.4636   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7957   -0.2237    2.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3336    0.6803    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0148   -0.8988    1.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7821   -0.4750    2.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1291   -0.1346    2.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6952    0.7828    1.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9460    1.3753   -0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5507    0.9996   -1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121   -2.6636   -1.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3425   -2.0069   -2.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8497   -1.2561   -2.0106 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
  3  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  1  0
 16  2  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1424                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.501   0.228   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       4.545   0.704   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.791  -0.201   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       7.466   3.415   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.021   2.169   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.561   2.169   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.037   0.704   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.791  -1.741   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.115   3.415   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080   0.228   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.839   4.821   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.998   3.253   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.124  -2.511   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.457  -2.511   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.124  -4.051   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.457  -4.051   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.791  -4.821   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    3    5   10                                                  
CONECT    3    2    7    8                                                  
CONECT    4    6   11   12                                                  
CONECT    5    2    6    9                                                  
CONECT    6    4    5    7                                                  
CONECT    7    1    3    6                                                  
CONECT    8    3   13   14                                                  
CONECT    9    5                                                            
CONECT   10    2                                                            
CONECT   11    4                                                            
CONECT   12    4                                                            
CONECT   13    8   15                                                       
CONECT   14    8   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   17                                                       
CONECT   17   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0015493
HETATM    1  C1  UNL     1      -2.149  -1.564  -1.652  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.191  -0.748  -0.820  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.544   0.222   0.092  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.836   0.675   0.461  1.00  0.00           N  
HETATM    5  C4  UNL     1      -3.448   1.770  -0.253  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.542   0.037   1.555  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.351   0.688   0.599  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.212   1.590   1.471  1.00  0.00           O  
HETATM    9  N2  UNL     1       0.682   0.024   0.016  1.00  0.00           N  
HETATM   10  C7  UNL     1       2.075   0.259   0.312  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.490  -0.063   1.588  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.800   0.121   1.978  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.655   0.640   1.028  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.262   0.969  -0.251  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.943   0.769  -0.599  1.00  0.00           C  
HETATM   16  N3  UNL     1       0.150  -0.825  -0.826  1.00  0.00           N  
HETATM   17  C13 UNL     1       0.896  -1.740  -1.665  1.00  0.00           C  
HETATM   18  H1  UNL     1      -3.106  -1.021  -1.787  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.285  -2.576  -1.218  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.679  -1.668  -2.649  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.089   2.380   0.421  1.00  0.00           H  
HETATM   22  H5  UNL     1      -4.086   1.417  -1.073  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.697   2.464  -0.690  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.796  -0.224   2.361  1.00  0.00           H  
HETATM   25  H8  UNL     1      -4.334   0.680   1.987  1.00  0.00           H  
HETATM   26  H9  UNL     1      -4.015  -0.899   1.193  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.782  -0.475   2.320  1.00  0.00           H  
HETATM   28  H11 UNL     1       4.129  -0.135   2.988  1.00  0.00           H  
HETATM   29  H12 UNL     1       5.695   0.783   1.349  1.00  0.00           H  
HETATM   30  H13 UNL     1       4.946   1.375  -0.983  1.00  0.00           H  
HETATM   31  H14 UNL     1       2.551   1.000  -1.580  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.112  -2.664  -1.069  1.00  0.00           H  
HETATM   33  H16 UNL     1       0.343  -2.007  -2.595  1.00  0.00           H  
HETATM   34  H17 UNL     1       1.850  -1.256  -2.011  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   16
CONECT    3    4    7
CONECT    4    5    6
CONECT    5   21   22   23
CONECT    6   24   25   26
CONECT    7    8    8    9
CONECT    9   10   16
CONECT   10   11   11   15
CONECT   11   12   27
CONECT   12   13   13   28
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   31
CONECT   16   17
CONECT   17   32   33   34
END

HMDB0015493
     RDKit          3D
Aminophenazone
 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.1489   -1.5640   -1.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1915   -0.7480   -0.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436    0.2218    0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8365    0.6752    0.4605 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4481    1.7699   -0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5415    0.0371    1.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3511    0.6876    0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124    1.5896    1.4712 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6819    0.0244    0.0159 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0746    0.2595    0.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898   -0.0634    1.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8002    0.1211    1.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6548    0.6399    1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2620    0.9695   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9429    0.7688   -0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497   -0.8253   -0.8261 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8962   -1.7399   -1.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1061   -1.0205   -1.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2848   -2.5759   -1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790   -1.6681   -2.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0888    2.3805    0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0862    1.4175   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6968    2.4636   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7957   -0.2237    2.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3336    0.6803    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0148   -0.8988    1.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7821   -0.4750    2.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1291   -0.1346    2.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6952    0.7828    1.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9460    1.3753   -0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5507    0.9996   -1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121   -2.6636   -1.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3425   -2.0069   -2.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8497   -1.2561   -2.0106 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
  3  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  1  0
 16  2  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(Dimethylamino)phenazone	ChEBI
1,5-Dimethyl-4-dimethylamino-2-phenyl-3-pyrazolone	ChEBI
1-Phenyl-2,3-dimethyl-4-(dimethylamino)-5-pyrazolone	ChEBI
1-Phenyl-2,3-dimethyl-4-dimethylaminopyrazol-5-one	ChEBI
2,3-Dimethyl-4-dimethylamino-1-phenyl-5-pyrazolone	ChEBI
3-Keto-1,5-dimethyl-4-dimethylamino-2-phenyl-2,3-dihydropyrazole	ChEBI
4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one	ChEBI
4-(Dimethylamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one	ChEBI
4-(Dimethylamino)antipyrine	ChEBI
4-Dimethylamino-1-phenyl-2,3-dimethylpyrazolone	ChEBI
4-Dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one	ChEBI
4-Dimethylamino-2,3-dimethyl-1-phenyl-5-pyrazolone	ChEBI
4-Dimethylaminoantipyrine	ChEBI
4-Dimethylaminophenazone	ChEBI
Aminofenazona	ChEBI
Aminofenazone	ChEBI
Aminophenazon	ChEBI
Aminophenazonum	ChEBI
Aminopyrine	ChEBI
Dimethylaminoantipyrine	ChEBI
Dimethylaminoazophene	ChEBI
Dimethylaminophenazon	ChEBI
Dimethylaminophenazone	ChEBI
Dimethylaminophenyldimethylpyrazolone	ChEBI
Dipyrine	ChEBI
Amidophen	HMDB
Amidophenazon	HMDB
Aminophenazone berlin-chemie brand	HMDB
Berlin-chemie brand OF aminophenazone	HMDB
Dimethyl-N-aminoantipyrine	HMDB
Berlin chemie brand OF aminophenazone	HMDB
Dimethyl N aminoantipyrine	HMDB
Eufibron	HMDB
Amidazophen	HMDB
Amidopyrine	HMDB

Chemical Formula

C₁₃H₁₇N₃O

Average Molecular Weight

231.2936

Monoisotopic Molecular Weight

231.137162181

IUPAC Name

4-(dimethylamino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one

Traditional Name

aminophenazone

CAS Registry Number

58-15-1

SMILES

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

InChI Identifier

InChI=1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3

InChI Key

RMMXTBMQSGEXHJ-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
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Monocyclic benzene moiety
Pyrazolinone
Benzenoid
Heteroaromatic compound
Vinylogous amide
Lactam
Tertiary amine
Azacycle
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:160246 )
pyrazolone (CHEBI:160246 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015493)

Source

Exogenous

Exogenous (HMDB: HMDB0015493)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	134.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	22.5 g/L	Not Available
LogP	1.00	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	22.5 g/L	ALOGPS
logP	0.94	ALOGPS
logP	1.15	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Basic)	3.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.79 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.11 m³·mol⁻¹	ChemAxon
Polarizability	25.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.602	31661259
DarkChem	[M-H]-	154.217	31661259
DeepCCS	[M+H]+	160.58	30932474
DeepCCS	[M-H]-	158.222	30932474
DeepCCS	[M-2H]-	191.126	30932474
DeepCCS	[M+Na]+	166.673	30932474
AllCCS	[M+H]+	151.9	32859911
AllCCS	[M+H-H2O]+	148.0	32859911
AllCCS	[M+NH4]+	155.5	32859911
AllCCS	[M+Na]+	156.5	32859911
AllCCS	[M-H]-	157.9	32859911
AllCCS	[M+Na-2H]-	157.9	32859911
AllCCS	[M+HCOO]-	158.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.79 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9174 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.82 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1194.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	237.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	136.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	55.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	273.1 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	323.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	139.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	748.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	257.5 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	693.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	227.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	219.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	341.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	267.6 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	121.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aminophenazone	CN(C)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1	2776.6	Standard polar	33892256
Aminophenazone	CN(C)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1	1953.9	Standard non polar	33892256
Aminophenazone	CN(C)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1	1914.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Aminophenazone EI-B (Non-derivatized)	splash10-053s-9250000000-c3308b81b44067a47f7e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Aminophenazone EI-B (Non-derivatized)	splash10-0a4i-9100000000-40e7051a3536ae680d1a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Aminophenazone EI-B (Non-derivatized)	splash10-053s-9250000000-c3308b81b44067a47f7e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Aminophenazone EI-B (Non-derivatized)	splash10-0a4i-9100000000-40e7051a3536ae680d1a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aminophenazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0159-4970000000-8cb60fc41366bf1c7f80	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aminophenazone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-ITFT , positive-QTOF	splash10-03dr-1900000000-49de43a88698c1df262b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-ITFT , positive-QTOF	splash10-001i-0190000000-d7bfbe39ac8d423c5cfd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-ITFT , positive-QTOF	splash10-03e9-4940000000-243b2713c256a2ab8b6c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-ITFT , positive-QTOF	splash10-03dj-9700000000-3ef4e69c38623bfd699f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-ITFT , positive-QTOF	splash10-06r2-9300000000-762e3df6382a5e2052a3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-ITFT , positive-QTOF	splash10-0592-9100000000-b9c175ecf48888c0267a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-ITFT , positive-QTOF	splash10-0a4j-9100000000-9fa64e7904c1473d9d32	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-ITFT , positive-QTOF	splash10-001i-0290000000-27bac0f1542859b73671	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-ITFT , positive-QTOF	splash10-03e9-4940000000-a4c3f3e347d595ad803e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-ITFT , positive-QTOF	splash10-03dj-9700000000-ac217c24c44682808465	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-ITFT , positive-QTOF	splash10-06xt-9300000000-f8259f5a45014efc58ee	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-ITFT , positive-QTOF	splash10-052b-9100000000-307762c9c387df2fcbf4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-ITFT , positive-QTOF	splash10-0a4j-9100000000-3c5267564fda210cc134	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-ITFT , positive-QTOF	splash10-03dr-1900000000-ab951ea405c6154ef630	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-QQ , positive-QTOF	splash10-001i-0090000000-2527cae3cd95916624e4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-QQ , positive-QTOF	splash10-03di-3910000000-f7ee26001f3fbe463bae	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-QQ , positive-QTOF	splash10-01vk-9400000000-243fad64356c2d2c4864	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-QQ , positive-QTOF	splash10-0592-9100000000-bbc78ee3e540bd560a88	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminophenazone LC-ESI-QQ , positive-QTOF	splash10-0aba-9000000000-1c4e7d6f8c8bbdc08335	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminophenazone 10V, Positive-QTOF	splash10-001i-0090000000-0896fba0b89cb8cb6ff5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminophenazone 20V, Positive-QTOF	splash10-001i-2390000000-eaa608d1cc64b37d59df	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminophenazone 40V, Positive-QTOF	splash10-001i-9100000000-db54dcd1f4d6da575bf1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminophenazone 10V, Negative-QTOF	splash10-00di-3920000000-00258f4a6df2920817cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminophenazone 20V, Negative-QTOF	splash10-0f8i-5790000000-dd0fbe214d13e5ebfde8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminophenazone 40V, Negative-QTOF	splash10-00l6-9300000000-18386f94d530fc45afc1	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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 DB01424	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01424	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01424

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00039051

Chemspider ID

5787

KEGG Compound ID

C07539

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Aminophenazone

METLIN ID

Not Available

PubChem Compound

6009

PDB ID

Not Available

ChEBI ID

160246

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

Rating D, Langhans CD: Breath tests: concepts, applications and limitations. Eur J Pediatr. 1997 Aug;156 Suppl 1:S18-23. [PubMed:9266210 ]

Showing metabocard for Aminophenazone (HMDB0015493)

MOL for HMDB0015493 (Aminophenazone)

3D MOL for HMDB0015493 (Aminophenazone)

3D SDF for HMDB0015493 (Aminophenazone)

3D-SDF for HMDB0015493 (Aminophenazone)

PDB for HMDB0015493 (Aminophenazone)

3D PDB for HMDB0015493 (Aminophenazone)

SMILES for HMDB0015493 (Aminophenazone)

INCHI for HMDB0015493 (Aminophenazone)

Structure for HMDB0015493 (Aminophenazone)

3D Structure for HMDB0015493 (Aminophenazone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra