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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9)transporters (1) Show 10 proteins XML

enzymes (9)transporters (1) Show 10 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:09 UTC

Update Date

2020-02-26 21:39:07 UTC

HMDB ID

HMDB0013839

Secondary Accession Numbers

HMDB13839

Metabolite Identification

Common Name

N-Desmethylaminopyrine

Description

N-Desmethylaminopyrine, also known as 4-methylaminophenazone or noramidopyrine, 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. N-Desmethylaminopyrine is a moderately basic compound (based on its pKa).

Structure

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

HMDB0013839
     RDKit          3D
N-Desmethylaminopyrine
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.6748    1.9696    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8826    1.6061   -0.4973 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7520    0.7613   -0.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6876   -0.6204   -0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8680   -1.4918   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4046   -0.9533   -0.2942 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0824   -2.3109   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534    0.1115   -0.0997 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7610    0.1590    0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3017    0.7591    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6679    0.8071    1.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5486    0.2500    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287   -0.3445   -0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6559   -0.3921   -0.7712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731    1.1695   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110    2.3628   -0.0108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1477    2.7688    1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7332    1.0606    1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6871    2.3176    0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1414    1.9679   -1.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877   -1.3306   -1.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042   -2.5508   -0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109   -1.1477   -0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6385   -2.9459    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0111   -2.6702   -1.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0750   -2.4465    0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121    1.1997    1.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0388    1.2831    2.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6254    0.3042    0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7014   -0.7848   -1.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411   -0.8683   -1.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 15  3  1  0
 14  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  5 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
M  END


  Mrv0541 10041214512D          

 16 17  0  0  0  0            999 V2000
    4.2032    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6486    0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839   -0.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7044   -1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5484   -0.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893   -0.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333    0.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8538    0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    3.1152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637    1.0206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    1.0206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  1  1  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 11  1  0  0  0  0
 13  2  1  0  0  0  0
 13 11  1  0  0  0  0
 14  3  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013839

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC1=C(C)N(C)N(C1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H15N3O/c1-9-11(13-2)12(16)15(14(9)3)10-7-5-4-6-8-10/h4-8,13H,1-3H3

> <INCHI_KEY>
JILCEWWZTBBOFS-UHFFFAOYSA-N

> <FORMULA>
C12H15N3O

> <MOLECULAR_WEIGHT>
217.267

> <EXACT_MASS>
217.121512117

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.98884347386228

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
0.7675469783333331

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.2599380223261547

> <JCHEM_POLAR_SURFACE_AREA>
35.58

> <JCHEM_REFRACTIVITY>
64.8163

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
noramidopyrine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0013839
     RDKit          3D
N-Desmethylaminopyrine
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.6748    1.9696    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8826    1.6061   -0.4973 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7520    0.7613   -0.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6876   -0.6204   -0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8680   -1.4918   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4046   -0.9533   -0.2942 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0824   -2.3109   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534    0.1115   -0.0997 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7610    0.1590    0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3017    0.7591    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6679    0.8071    1.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5486    0.2500    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287   -0.3445   -0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6559   -0.3921   -0.7712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731    1.1695   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110    2.3628   -0.0108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1477    2.7688    1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7332    1.0606    1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6871    2.3176    0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1414    1.9679   -1.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877   -1.3306   -1.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042   -2.5508   -0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109   -1.1477   -0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6385   -2.9459    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0111   -2.6702   -1.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0750   -2.4465    0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121    1.1997    1.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0388    1.2831    2.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6254    0.3042    0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7014   -0.7848   -1.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411   -0.8683   -1.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 15  3  1  0
 14  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  5 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
M  END

HEADER    PROTEIN                                 04-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-OCT-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   10                                                       
CONECT    8    6   10                                                       
CONECT    9    1   11   14                                                  
CONECT   10    7    8   15                                                  
CONECT   11    9   12   13                                                  
CONECT   12   11   15   16                                                  
CONECT   13    2   11                                                       
CONECT   14    3    9   15                                                  
CONECT   15   10   12   14                                                  
CONECT   16   12                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0013839
HETATM    1  C1  UNL     1      -3.675   1.970   0.654  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.883   1.606  -0.497  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.752   0.761  -0.382  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.688  -0.620  -0.470  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.868  -1.492  -0.717  1.00  0.00           C  
HETATM    6  N2  UNL     1      -0.405  -0.953  -0.294  1.00  0.00           N  
HETATM    7  C5  UNL     1       0.082  -2.311  -0.316  1.00  0.00           C  
HETATM    8  N3  UNL     1       0.353   0.112  -0.100  1.00  0.00           N  
HETATM    9  C6  UNL     1       1.761   0.159   0.123  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.302   0.759   1.246  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.668   0.807   1.466  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.549   0.250   0.559  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.029  -0.345  -0.551  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.656  -0.392  -0.771  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.473   1.169  -0.153  1.00  0.00           C  
HETATM   16  O1  UNL     1      -0.111   2.363  -0.011  1.00  0.00           O  
HETATM   17  H1  UNL     1      -3.148   2.769   1.219  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.733   1.061   1.316  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.687   2.318   0.365  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.141   1.968  -1.433  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.188  -1.331  -1.766  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.604  -2.551  -0.525  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.711  -1.148  -0.078  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.639  -2.946   0.247  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.011  -2.670  -1.379  1.00  0.00           H  
HETATM   26  H10 UNL     1       1.075  -2.446   0.104  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.612   1.200   1.964  1.00  0.00           H  
HETATM   28  H12 UNL     1       4.039   1.283   2.351  1.00  0.00           H  
HETATM   29  H13 UNL     1       5.625   0.304   0.762  1.00  0.00           H  
HETATM   30  H14 UNL     1       4.701  -0.785  -1.270  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.241  -0.868  -1.661  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20
CONECT    3    4    4   15
CONECT    4    5    6
CONECT    5   21   22   23
CONECT    6    7    8
CONECT    7   24   25   26
CONECT    8    9   15
CONECT    9   10   10   14
CONECT   10   11   27
CONECT   11   12   12   28
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   31
CONECT   15   16   16
END

HMDB0013839
     RDKit          3D
N-Desmethylaminopyrine
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.6748    1.9696    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8826    1.6061   -0.4973 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7520    0.7613   -0.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6876   -0.6204   -0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8680   -1.4918   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4046   -0.9533   -0.2942 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0824   -2.3109   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534    0.1115   -0.0997 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7610    0.1590    0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3017    0.7591    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6679    0.8071    1.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5486    0.2500    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287   -0.3445   -0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6559   -0.3921   -0.7712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731    1.1695   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110    2.3628   -0.0108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1477    2.7688    1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7332    1.0606    1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6871    2.3176    0.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1414    1.9679   -1.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877   -1.3306   -1.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042   -2.5508   -0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109   -1.1477   -0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6385   -2.9459    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0111   -2.6702   -1.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0750   -2.4465    0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121    1.1997    1.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0388    1.2831    2.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6254    0.3042    0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7014   -0.7848   -1.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411   -0.8683   -1.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 15  3  1  0
 14  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  5 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Methylaminoantipyrine	ChEBI
4-Methylaminophenazone	ChEBI
4-Monomethylaminoantipyrine	ChEBI
4-Monomethylaminophenazone	ChEBI
Noramidopyrine	ChEBI
Noraminopyrine	ChEBI
Monomethylaminoantipyrine	HMDB
Methylaminoantipyrine	HMDB
Noramidopyrine mesylate, sodium salt	HMDB

Chemical Formula

C₁₂H₁₅N₃O

Average Molecular Weight

217.267

Monoisotopic Molecular Weight

217.121512117

IUPAC Name

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

Traditional Name

noramidopyrine

CAS Registry Number

Not Available

SMILES

CNC1=C(C)N(C)N(C1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H15N3O/c1-9-11(13-2)12(16)15(14(9)3)10-7-5-4-6-8-10/h4-8,13H,1-3H3

InChI Key

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazoles (CHEBI:73261 )
secondary amino compound (CHEBI:73261 )

Ontology

Not Available

Liver (HMDB: HMDB0013839)
Kidney (HMDB: HMDB0013839)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013839)

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
Water Solubility	10.9 g/L	ALOGPS
logP	0.89	ALOGPS
logP	0.77	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	1.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.58 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	64.82 m³·mol⁻¹	ChemAxon
Polarizability	23.99 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]+	150.675	31661259
DarkChem	[M-H]-	149.419	31661259
DeepCCS	[M+H]+	155.697	30932474
DeepCCS	[M-H]-	153.339	30932474
DeepCCS	[M-2H]-	186.357	30932474
DeepCCS	[M+Na]+	161.79	30932474
AllCCS	[M+H]+	148.6	32859911
AllCCS	[M+H-H2O]+	144.6	32859911
AllCCS	[M+NH4]+	152.4	32859911
AllCCS	[M+Na]+	153.4	32859911
AllCCS	[M-H]-	152.7	32859911
AllCCS	[M+Na-2H]-	152.7	32859911
AllCCS	[M+HCOO]-	152.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethylaminopyrine	CNC1=C(C)N(C)N(C1=O)C1=CC=CC=C1	2895.3	Standard polar	33892256
N-Desmethylaminopyrine	CNC1=C(C)N(C)N(C1=O)C1=CC=CC=C1	1931.3	Standard non polar	33892256
N-Desmethylaminopyrine	CNC1=C(C)N(C)N(C1=O)C1=CC=CC=C1	2055.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethylaminopyrine,1TMS,isomer #1	CC1=C(N(C)[Si](C)(C)C)C(=O)N(C2=CC=CC=C2)N1C	1953.0	Semi standard non polar	33892256
N-Desmethylaminopyrine,1TMS,isomer #1	CC1=C(N(C)[Si](C)(C)C)C(=O)N(C2=CC=CC=C2)N1C	2001.0	Standard non polar	33892256
N-Desmethylaminopyrine,1TMS,isomer #1	CC1=C(N(C)[Si](C)(C)C)C(=O)N(C2=CC=CC=C2)N1C	2345.0	Standard polar	33892256
N-Desmethylaminopyrine,1TBDMS,isomer #1	CC1=C(N(C)[Si](C)(C)C(C)(C)C)C(=O)N(C2=CC=CC=C2)N1C	2211.4	Semi standard non polar	33892256
N-Desmethylaminopyrine,1TBDMS,isomer #1	CC1=C(N(C)[Si](C)(C)C(C)(C)C)C(=O)N(C2=CC=CC=C2)N1C	2185.1	Standard non polar	33892256
N-Desmethylaminopyrine,1TBDMS,isomer #1	CC1=C(N(C)[Si](C)(C)C(C)(C)C)C(=O)N(C2=CC=CC=C2)N1C	2500.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - N-Desmethylaminopyrine EI-B (Non-derivatized)	splash10-0aor-9140000000-9160708910f96853b852	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Desmethylaminopyrine EI-B (Non-derivatized)	splash10-0aor-9140000000-9160708910f96853b852	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethylaminopyrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gb9-5950000000-9401f6218d88a8f1c0b0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethylaminopyrine 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 - N-Desmethylaminopyrine 10V, Positive-QTOF	splash10-014i-2090000000-4de7ddddac4eb0de4f53	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylaminopyrine 20V, Positive-QTOF	splash10-0a4i-9120000000-a5a27d6ef88f8363cbf6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylaminopyrine 40V, Positive-QTOF	splash10-0q29-9000000000-d702c9e101114cd74515	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylaminopyrine 10V, Negative-QTOF	splash10-00di-4920000000-04531eaac39709559895	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylaminopyrine 20V, Negative-QTOF	splash10-00rl-8920000000-7501487c3f63cabcad28	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylaminopyrine 40V, Negative-QTOF	splash10-0006-9100000000-6960b2ee9cd7c49eded7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylaminopyrine 10V, Negative-QTOF	splash10-014i-0090000000-15430e998fe5883b91b0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylaminopyrine 20V, Negative-QTOF	splash10-014i-4490000000-75bc60532afc2a2b3907	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylaminopyrine 40V, Negative-QTOF	splash10-0006-9210000000-3646dfbf34a6dc559c2f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylaminopyrine 10V, Positive-QTOF	splash10-014i-0090000000-4208c670efe1c11ffc9a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylaminopyrine 20V, Positive-QTOF	splash10-014i-1190000000-b81af9ed68e9c4e07c3e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylaminopyrine 40V, Positive-QTOF	splash10-0006-9000000000-a45bd402e13e1f1c7688	2021-09-24	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

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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

Not Available

METLIN ID

Not Available

PubChem Compound

10618

PDB ID

Not Available

ChEBI ID

73261

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

Ojha A, Rathod R, Padh H: Quantification of 4-methylaminoantipyrine, the active metabolite of dipyrone, in human plasma. Bioanalysis. 2009 May;1(2):293-8. doi: 10.4155/bio.09.26. [PubMed:21083168 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Enzyme Details

4. Steroid 17-alpha-hydroxylase/17,20 lyase

General function:: Involved in monooxygenase activity
Specific function:: Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Gene Name:: CYP17A1
Uniprot ID:: P05093
Molecular weight:: 57369.995

References

Enzyme Details

5. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Enzyme Details

6. Cytochrome P450 2C18

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

References

Enzyme Details

7. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

References

Enzyme Details

8. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Enzyme Details

9. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Showing metabocard for N-Desmethylaminopyrine (HMDB0013839)

MOL for HMDB0013839 (N-Desmethylaminopyrine)

3D MOL for HMDB0013839 (N-Desmethylaminopyrine)

3D SDF for HMDB0013839 (N-Desmethylaminopyrine)

3D-SDF for HMDB0013839 (N-Desmethylaminopyrine)

PDB for HMDB0013839 (N-Desmethylaminopyrine)

3D PDB for HMDB0013839 (N-Desmethylaminopyrine)

SMILES for HMDB0013839 (N-Desmethylaminopyrine)

INCHI for HMDB0013839 (N-Desmethylaminopyrine)

Structure for HMDB0013839 (N-Desmethylaminopyrine)

3D Structure for HMDB0013839 (N-Desmethylaminopyrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

References

References

References

References

References

Transporters

References