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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:21:14 UTC

Update Date

2021-09-26 22:55:20 UTC

HMDB ID

HMDB0246326

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Acetamidoantipyrine

Description

4-Acetamidoantipyrine 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. 4-Acetamidoantipyrine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 4-Acetamidoantipyrine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-acetamidoantipyrine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Acetamidoantipyrine 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

HMDB0246326
     RDKit          3D
4-Acetamidoantipyrine
 33 34  0  0  0  0  0  0  0  0999 V2000
    5.1870    0.5346    0.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7744    0.1446    0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4471   -1.0016    0.9261 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7972    0.9921   -0.0991 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4544    0.5406   -0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9613   -0.1528   -1.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983   -0.5599   -2.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3335   -0.4013   -1.0287 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2769   -1.1150   -1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6898    0.0897    0.1464 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9988    0.0070    0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0701    0.7268    0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3322    0.6943    0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5632   -0.1184    1.8667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5143   -0.8681    2.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2496   -0.8008    1.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3936    0.6702    0.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4637    1.2551    1.7747 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8035   -0.0939   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5239    0.3050    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3143    1.6105    0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0871    1.9308   -0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7080   -0.1458   -2.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1479   -0.2166   -3.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6726   -1.6658   -2.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1976   -0.4972   -2.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183   -2.0508   -1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7774   -1.3609   -2.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809    1.3593   -0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1746    1.2567    0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5448   -0.1894    2.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7450   -1.4916    3.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4672   -1.3891    2.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  2  0
 17  5  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
M  END


  Mrv1533004201502112D          

 18 19  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 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 N   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   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 N   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
   -1.4884   -3.7557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390   -2.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -1.4675    0.0000 C   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
    3.1227   -0.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7358   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5642   -1.7646    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
  1  2  1  0  0  0  0
  2  3  1  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  2  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  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246326

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1N(C(=O)C(NC(C)=O)=C1C)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H15N3O2/c1-9-12(14-10(2)17)13(18)16(15(9)3)11-7-5-4-6-8-11/h4-8H,1-3H3,(H,14,17)

> <INCHI_KEY>
OIAGWXKSCXPNNZ-UHFFFAOYSA-N

> <FORMULA>
C13H15N3O2

> <MOLECULAR_WEIGHT>
245.282

> <EXACT_MASS>
245.116426735

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.220960151764025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
0.15381318766666627

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.519155217678794

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1636330271538635

> <JCHEM_POLAR_SURFACE_AREA>
52.65

> <JCHEM_REFRACTIVITY>
69.48550000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246326
     RDKit          3D
4-Acetamidoantipyrine
 33 34  0  0  0  0  0  0  0  0999 V2000
    5.1870    0.5346    0.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7744    0.1446    0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4471   -1.0016    0.9261 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7972    0.9921   -0.0991 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4544    0.5406   -0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9613   -0.1528   -1.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983   -0.5599   -2.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3335   -0.4013   -1.0287 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2769   -1.1150   -1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6898    0.0897    0.1464 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9988    0.0070    0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0701    0.7268    0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3322    0.6943    0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5632   -0.1184    1.8667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5143   -0.8681    2.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2496   -0.8008    1.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3936    0.6702    0.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4637    1.2551    1.7747 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8035   -0.0939   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5239    0.3050    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3143    1.6105    0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0871    1.9308   -0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7080   -0.1458   -2.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1479   -0.2166   -3.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6726   -1.6658   -2.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1976   -0.4972   -2.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183   -2.0508   -1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7774   -1.3609   -2.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809    1.3593   -0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1746    1.2567    0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5448   -0.1894    2.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7450   -1.4916    3.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4672   -1.3891    2.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  2  0
 17  5  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
M  END

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       2.580  -3.215   0.000  0.00  0.00           N+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  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.342  -5.926   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.873  -5.765   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.778  -7.011   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.499  -4.358   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.044  -2.739   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.364  -1.233   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.829  -0.757   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.973  -1.788   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.653  -3.294   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.189  -3.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   13                                                  
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                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    3   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0246326
HETATM    1  C1  UNL     1       5.187   0.535   0.651  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.774   0.145   0.498  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.447  -1.002   0.926  1.00  0.00           O  
HETATM    4  N1  UNL     1       2.797   0.992  -0.099  1.00  0.00           N  
HETATM    5  C3  UNL     1       1.454   0.541  -0.209  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.961  -0.153  -1.291  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.698  -0.560  -2.521  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.334  -0.401  -1.029  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.277  -1.115  -1.888  1.00  0.00           C  
HETATM   10  N3  UNL     1      -0.690   0.090   0.146  1.00  0.00           N  
HETATM   11  C7  UNL     1      -1.999   0.007   0.743  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.070   0.727   0.256  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.332   0.694   0.773  1.00  0.00           C  
HETATM   14  C10 UNL     1      -4.563  -0.118   1.867  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.514  -0.868   2.399  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.250  -0.801   1.838  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.394   0.670   0.662  1.00  0.00           C  
HETATM   18  O2  UNL     1       0.464   1.255   1.775  1.00  0.00           O  
HETATM   19  H1  UNL     1       5.803  -0.094  -0.054  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.524   0.305   1.680  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.314   1.611   0.449  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.087   1.931  -0.445  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.708  -0.146  -2.525  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.148  -0.217  -3.435  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.673  -1.666  -2.546  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.198  -0.497  -2.036  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.618  -2.051  -1.410  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.777  -1.361  -2.826  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.881   1.359  -0.599  1.00  0.00           H  
HETATM   30  H12 UNL     1      -5.175   1.257   0.394  1.00  0.00           H  
HETATM   31  H13 UNL     1      -5.545  -0.189   2.325  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.745  -1.492   3.259  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.467  -1.389   2.272  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    4
CONECT    4    5   22
CONECT    5    6    6   17
CONECT    6    7    8
CONECT    7   23   24   25
CONECT    8    9   10
CONECT    9   26   27   28
CONECT   10   11   17
CONECT   11   12   12   16
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15   31
CONECT   15   16   16   32
CONECT   16   33
CONECT   17   18   18
END

HMDB0246326
     RDKit          3D
4-Acetamidoantipyrine
 33 34  0  0  0  0  0  0  0  0999 V2000
    5.1870    0.5346    0.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7744    0.1446    0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4471   -1.0016    0.9261 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7972    0.9921   -0.0991 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4544    0.5406   -0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9613   -0.1528   -1.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983   -0.5599   -2.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3335   -0.4013   -1.0287 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2769   -1.1150   -1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6898    0.0897    0.1464 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9988    0.0070    0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0701    0.7268    0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3322    0.6943    0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5632   -0.1184    1.8667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5143   -0.8681    2.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2496   -0.8008    1.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3936    0.6702    0.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4637    1.2551    1.7747 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8035   -0.0939   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5239    0.3050    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3143    1.6105    0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0871    1.9308   -0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7080   -0.1458   -2.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1479   -0.2166   -3.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6726   -1.6658   -2.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1976   -0.4972   -2.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183   -2.0508   -1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7774   -1.3609   -2.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809    1.3593   -0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1746    1.2567    0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5448   -0.1894    2.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7450   -1.4916    3.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4672   -1.3891    2.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  2  0
 17  5  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Acetaminoantipyrine	ChEBI
4-Acetoaminoantipyrine	ChEBI
Acetylaminoantipyrine	ChEBI
4-Acetylaminoantipyrine	HMDB
N-Acetylaminoantipyrine	HMDB

Chemical Formula

C₁₃H₁₅N₃O₂

Average Molecular Weight

245.282

Monoisotopic Molecular Weight

245.116426735

IUPAC Name

N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide

Traditional Name

N-(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)acetamide

CAS Registry Number

Not Available

SMILES

CN1N(C(=O)C(NC(C)=O)=C1C)C1=CC=CC=C1

InChI Identifier

InChI=1S/C13H15N3O2/c1-9-12(14-10(2)17)13(18)16(15(9)3)11-7-5-4-6-8-11/h4-8H,1-3H3,(H,14,17)

InChI Key

OIAGWXKSCXPNNZ-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
N-acetylarylamine
N-arylamide
Monocyclic benzene moiety
Pyrazolinone
Benzenoid
Vinylogous amide
Acetamide
Heteroaromatic compound
Secondary carboxylic acid amide
Lactam
Carboxamide group
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazoles (CHEBI:83513 )
acetamides (CHEBI:83513 )

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	1.01	ALOGPS
logP	0.15	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	12.52	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.65 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.49 m³·mol⁻¹	ChemAxon
Polarizability	26.22 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]+	155.202	30932474
DeepCCS	[M-H]-	152.806	30932474
DeepCCS	[M-2H]-	185.93	30932474
DeepCCS	[M+Na]+	161.115	30932474
AllCCS	[M+H]+	155.5	32859911
AllCCS	[M+H-H2O]+	151.7	32859911
AllCCS	[M+NH4]+	158.9	32859911
AllCCS	[M+Na]+	159.9	32859911
AllCCS	[M-H]-	159.6	32859911
AllCCS	[M+Na-2H]-	159.6	32859911
AllCCS	[M+HCOO]-	159.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.6944 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.76 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1026.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	223.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	107.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	48.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	250.7 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	322.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	144.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	657.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	195.3 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	761.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	216.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	337.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	282.3 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	255.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Acetamidoantipyrine	CN1N(C(=O)C(NC(C)=O)=C1C)C1=CC=CC=C1	3056.9	Standard polar	33892256
4-Acetamidoantipyrine	CN1N(C(=O)C(NC(C)=O)=C1C)C1=CC=CC=C1	2095.5	Standard non polar	33892256
4-Acetamidoantipyrine	CN1N(C(=O)C(NC(C)=O)=C1C)C1=CC=CC=C1	2327.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Acetamidoantipyrine,1TMS,isomer #1	CC(=O)N(C1=C(C)N(C)N(C2=CC=CC=C2)C1=O)[Si](C)(C)C	2055.5	Semi standard non polar	33892256
4-Acetamidoantipyrine,1TMS,isomer #1	CC(=O)N(C1=C(C)N(C)N(C2=CC=CC=C2)C1=O)[Si](C)(C)C	2139.9	Standard non polar	33892256
4-Acetamidoantipyrine,1TMS,isomer #1	CC(=O)N(C1=C(C)N(C)N(C2=CC=CC=C2)C1=O)[Si](C)(C)C	2669.5	Standard polar	33892256
4-Acetamidoantipyrine,1TBDMS,isomer #1	CC(=O)N(C1=C(C)N(C)N(C2=CC=CC=C2)C1=O)[Si](C)(C)C(C)(C)C	2299.5	Semi standard non polar	33892256
4-Acetamidoantipyrine,1TBDMS,isomer #1	CC(=O)N(C1=C(C)N(C)N(C2=CC=CC=C2)C1=O)[Si](C)(C)C(C)(C)C	2300.1	Standard non polar	33892256
4-Acetamidoantipyrine,1TBDMS,isomer #1	CC(=O)N(C1=C(C)N(C)N(C2=CC=CC=C2)C1=O)[Si](C)(C)C(C)(C)C	2775.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Acetamidoantipyrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g59-4790000000-417ba707efc84a6c6819	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Acetamidoantipyrine 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 - 4-Acetamidoantipyrine 40V, Positive-QTOF	splash10-008c-0900000000-83d1ff371690052cd487	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 30V, Positive-QTOF	splash10-0pdi-0940000000-a201ff2640a0846849f6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 35V, Positive-QTOF	splash10-004i-0090000000-4c363f26ce86c080f001	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 55V, Positive-QTOF	splash10-0ue9-8930000000-eb8143bff273a8db7798	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 35V, Positive-QTOF	splash10-004i-0090000000-bd9038de40e6acd6eb17	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 50V, Positive-QTOF	splash10-000x-0900000000-1dea69f3926567adba08	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 50V, Positive-QTOF	splash10-000y-0900000000-37b8823300f3e09834b7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 15V, Positive-QTOF	splash10-0002-0090000000-af268200b0790a435d11	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 30V, Positive-QTOF	splash10-004i-0090000000-2d4ba29a325b9d43cfc5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 50V, Positive-QTOF	splash10-000y-0900000000-d6c698034db599229f4d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 55V, Positive-QTOF	splash10-004i-0090000000-a4a4f5dfb098dd89c29e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 75V, Positive-QTOF	splash10-0f89-9400000000-f1581e7c5ac2bcb8f2b1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 90V, Positive-QTOF	splash10-001i-9300000000-ec7e2dc85de9c3496bd1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 60V, Positive-QTOF	splash10-0f89-9710000000-a7bf7cfd48b545d5e50a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 60V, Positive-QTOF	splash10-0f89-9710000000-182468fbdca0a365bf45	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 35V, Positive-QTOF	splash10-004i-0090000000-0f8953497229fa1abf63	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 80V, Positive-QTOF	splash10-0f89-9500000000-0fc52f6ab12fe8d5642d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 45V, Positive-QTOF	splash10-0ugi-4590000000-f6589ce3610926578197	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Acetamidoantipyrine 45V, Positive-QTOF	splash10-0ugi-5590000000-54756eefc4b6e984ecdb	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetamidoantipyrine 10V, Positive-QTOF	splash10-0f6t-0190000000-d1aae307767141af1cab	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetamidoantipyrine 20V, Positive-QTOF	splash10-0pb9-9160000000-4454599ea3f9778d48ef	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetamidoantipyrine 40V, Positive-QTOF	splash10-0f89-9100000000-ffc177034f7186be61bb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetamidoantipyrine 10V, Negative-QTOF	splash10-00dl-4930000000-22e4c8d8af84a4e1bfca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetamidoantipyrine 20V, Negative-QTOF	splash10-0udl-7980000000-53b7e76538554032ec7f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetamidoantipyrine 40V, Negative-QTOF	splash10-0006-9300000000-b2ebf7079001e3a1b0d7	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)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

59166

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65743

PDB ID

Not Available

ChEBI ID

83513

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 4-Acetamidoantipyrine (HMDB0246326)

MOL for HMDB0246326 (4-Acetamidoantipyrine)

3D MOL for HMDB0246326 (4-Acetamidoantipyrine)

3D SDF for HMDB0246326 (4-Acetamidoantipyrine)

3D-SDF for HMDB0246326 (4-Acetamidoantipyrine)

PDB for HMDB0246326 (4-Acetamidoantipyrine)

3D PDB for HMDB0246326 (4-Acetamidoantipyrine)

SMILES for HMDB0246326 (4-Acetamidoantipyrine)

INCHI for HMDB0246326 (4-Acetamidoantipyrine)

Structure for HMDB0246326 (4-Acetamidoantipyrine)

3D Structure for HMDB0246326 (4-Acetamidoantipyrine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra