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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:47:38 UTC

Update Date

2022-03-07 02:57:13 UTC

HMDB ID

HMDB0041914

Secondary Accession Numbers

HMDB41914

Metabolite Identification

Common Name

Ketophenylbutazone

Description

Ketophenylbutazone, also known as kebuzonum or quebuzona, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Based on a literature review a significant number of articles have been published on Ketophenylbutazone.

Structure

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

HMDB0041914
     RDKit          3D
Ketophenylbutazone
 42 44  0  0  0  0  0  0  0  0999 V2000
    5.8443   -0.1155    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3954   -0.1240    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119   -0.5164    1.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4712    0.3511   -0.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3655   -0.6429   -0.7294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759   -0.2734   -1.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527    0.9809   -1.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526    2.1326   -1.9347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4999    0.6299   -0.7346 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2321    1.5811    0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225    2.2589   -0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0351    3.1795    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6713    3.4767    1.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932    2.8302    2.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8741    1.8843    1.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895   -0.7423   -0.8721 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6922   -1.5214   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956   -2.5553    0.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4040   -3.2880    1.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7219   -3.0271    0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0105   -1.9904    0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0103   -1.2388   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869   -1.3106   -1.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3441   -2.3860   -2.3532 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1763    0.7985   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0497   -0.9729   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4227   -0.2557    1.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0634    1.3342   -0.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785    0.4895   -1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7651   -1.6487   -0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7655   -0.7960    0.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8310   -0.2568   -2.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5980    2.0137   -1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8879    3.6658   -0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2440    4.2121    2.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3267    3.0847    3.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0445    1.3971    1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3551   -2.7423    0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615   -4.1131    1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5344   -3.5979    1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0655   -1.7705   -0.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2830   -0.4147   -1.2143 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  1  0
  6  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
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16 23  1  0
 23 24  2  0
 23  6  1  0
 15 10  1  0
 22 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
M  END

  Mrv0541 09131211472D          

 24 26  0  0  0  0            999 V2000
    6.2140    1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2701    2.5701    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
   -0.0986    1.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3430    3.1221    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
    0.6860    1.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1276    2.8672    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
    4.8163    1.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2032    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6010    1.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    2.0602    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
    3.4186    1.8053    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
    3.1637    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837    1.8053    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
    5.7725    2.5701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    3.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6486    0.3532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 13 12  1  0  0  0  0
 14  1  1  0  0  0  0
 14 12  1  0  0  0  0
 15  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  2  0  0  0  0
 16 11  1  0  0  0  0
 17 13  1  0  0  0  0
 18 17  1  0  0  0  0
 19 17  1  0  0  0  0
 20 15  1  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 21 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 14  2  0  0  0  0
 23 18  2  0  0  0  0
 24 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041914

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CCC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H18N2O3/c1-14(22)12-13-17-18(23)20(15-8-4-2-5-9-15)21(19(17)24)16-10-6-3-7-11-16/h2-11,17H,12-13H2,1H3

> <INCHI_KEY>
LGYTZKPVOAIUKX-UHFFFAOYSA-N

> <FORMULA>
C19H18N2O3

> <MOLECULAR_WEIGHT>
322.3578

> <EXACT_MASS>
322.131742452

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.64442141283973

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(3-oxobutyl)-1,2-diphenylpyrazolidine-3,5-dione

> <ALOGPS_LOGP>
1.99

> <JCHEM_LOGP>
2.700612858333333

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.551733229842625

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.1666921906674865

> <JCHEM_PKA_STRONGEST_BASIC>
-7.271719184488955

> <JCHEM_POLAR_SURFACE_AREA>
57.690000000000005

> <JCHEM_REFRACTIVITY>
89.37379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
kebuzone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041914
     RDKit          3D
Ketophenylbutazone
 42 44  0  0  0  0  0  0  0  0999 V2000
    5.8443   -0.1155    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3954   -0.1240    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119   -0.5164    1.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4712    0.3511   -0.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3655   -0.6429   -0.7294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759   -0.2734   -1.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527    0.9809   -1.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526    2.1326   -1.9347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4999    0.6299   -0.7346 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2321    1.5811    0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225    2.2589   -0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0351    3.1795    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6713    3.4767    1.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932    2.8302    2.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8741    1.8843    1.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895   -0.7423   -0.8721 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6922   -1.5214   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956   -2.5553    0.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4040   -3.2880    1.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7219   -3.0271    0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0105   -1.9904    0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0103   -1.2388   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869   -1.3106   -1.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3441   -2.3860   -2.3532 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1763    0.7985   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0497   -0.9729   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4227   -0.2557    1.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0634    1.3342   -0.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785    0.4895   -1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7651   -1.6487   -0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7655   -0.7960    0.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8310   -0.2568   -2.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5980    2.0137   -1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8879    3.6658   -0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2440    4.2121    2.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3267    3.0847    3.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0445    1.3971    1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3551   -2.7423    0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615   -4.1131    1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5344   -3.5979    1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0655   -1.7705   -0.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2830   -0.4147   -1.2143 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  1  0
  6  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
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16 23  1  0
 23 24  2  0
 23  6  1  0
 15 10  1  0
 22 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0      11.599   2.261   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.504   4.798   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.650  -1.833   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.184   3.291   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.640   5.828   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.182  -1.993   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.024  -0.426   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.281   2.815   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.105   5.352   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.087  -0.748   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.929   0.820   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.990   2.815   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.846   3.846   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.455   3.291   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.425   3.846   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.460   0.659   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.381   3.370   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.136   4.275   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.906   1.905   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       3.890   3.370   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       4.366   1.905   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      10.775   4.798   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.136   5.815   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.811   0.659   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2    4    5                                                       
CONECT    3    6    7                                                       
CONECT    4    2    8                                                       
CONECT    5    2    9                                                       
CONECT    6    3   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   15                                                       
CONECT    9    5   15                                                       
CONECT   10    6   16                                                       
CONECT   11    7   16                                                       
CONECT   12   13   14                                                       
CONECT   13   12   17                                                       
CONECT   14    1   12   22                                                  
CONECT   15    8    9   20                                                  
CONECT   16   10   11   21                                                  
CONECT   17   13   18   19                                                  
CONECT   18   17   20   23                                                  
CONECT   19   17   21   24                                                  
CONECT   20   15   18   21                                                  
CONECT   21   16   19   20                                                  
CONECT   22   14                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0041914
HETATM    1  C1  UNL     1       5.844  -0.116   0.305  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.395  -0.124   0.539  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.912  -0.516   1.588  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.471   0.351  -0.527  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.365  -0.643  -0.729  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.376  -0.273  -1.796  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.653   0.981  -1.542  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.953   2.133  -1.935  1.00  0.00           O  
HETATM    9  N1  UNL     1      -0.500   0.630  -0.735  1.00  0.00           N  
HETATM   10  C7  UNL     1      -1.232   1.581   0.016  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.323   2.259  -0.487  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.035   3.180   0.214  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.671   3.477   1.510  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.593   2.830   2.058  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.874   1.884   1.316  1.00  0.00           C  
HETATM   16  N2  UNL     1      -0.690  -0.742  -0.872  1.00  0.00           N  
HETATM   17  C13 UNL     1      -1.692  -1.521  -0.251  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.396  -2.555   0.611  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.404  -3.288   1.179  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.722  -3.027   0.920  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.011  -1.990   0.056  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.010  -1.239  -0.529  1.00  0.00           C  
HETATM   23  C19 UNL     1       0.287  -1.311  -1.737  1.00  0.00           C  
HETATM   24  O3  UNL     1       0.344  -2.386  -2.353  1.00  0.00           O  
HETATM   25  H1  UNL     1       6.176   0.798  -0.197  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.050  -0.973  -0.395  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.423  -0.256   1.251  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.063   1.334  -0.204  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.979   0.489  -1.501  1.00  0.00           H  
HETATM   30  H6  UNL     1       2.765  -1.649  -0.987  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.766  -0.796   0.218  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.831  -0.257  -2.808  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.598   2.014  -1.507  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.888   3.666  -0.267  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.244   4.212   2.061  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.327   3.085   3.083  1.00  0.00           H  
HETATM   37  H13 UNL     1      -0.044   1.397   1.775  1.00  0.00           H  
HETATM   38  H14 UNL     1      -0.355  -2.742   0.807  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.161  -4.113   1.864  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.534  -3.598   1.366  1.00  0.00           H  
HETATM   41  H17 UNL     1      -5.066  -1.771  -0.162  1.00  0.00           H  
HETATM   42  H18 UNL     1      -3.283  -0.415  -1.214  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   23   32
CONECT    7    8    8    9
CONECT    9   10   16
CONECT   10   11   11   15
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   14   35
CONECT   14   15   15   36
CONECT   15   37
CONECT   16   17   23
CONECT   17   18   18   22
CONECT   18   19   38
CONECT   19   20   20   39
CONECT   20   21   40
CONECT   21   22   22   41
CONECT   22   42
CONECT   23   24   24
END

HMDB0041914
     RDKit          3D
Ketophenylbutazone
 42 44  0  0  0  0  0  0  0  0999 V2000
    5.8443   -0.1155    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3954   -0.1240    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119   -0.5164    1.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4712    0.3511   -0.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3655   -0.6429   -0.7294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759   -0.2734   -1.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527    0.9809   -1.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526    2.1326   -1.9347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4999    0.6299   -0.7346 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2321    1.5811    0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225    2.2589   -0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0351    3.1795    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6713    3.4767    1.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932    2.8302    2.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8741    1.8843    1.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895   -0.7423   -0.8721 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6922   -1.5214   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956   -2.5553    0.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4040   -3.2880    1.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7219   -3.0271    0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0105   -1.9904    0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0103   -1.2388   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869   -1.3106   -1.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3441   -2.3860   -2.3532 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1763    0.7985   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0497   -0.9729   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4227   -0.2557    1.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0634    1.3342   -0.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785    0.4895   -1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7651   -1.6487   -0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7655   -0.7960    0.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8310   -0.2568   -2.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5980    2.0137   -1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8879    3.6658   -0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2440    4.2121    2.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3267    3.0847    3.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0445    1.3971    1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3551   -2.7423    0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615   -4.1131    1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5344   -3.5979    1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0655   -1.7705   -0.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2830   -0.4147   -1.2143 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  1  0
  6  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
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16 23  1  0
 23 24  2  0
 23  6  1  0
 15 10  1  0
 22 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Diphenyl-4-(gamma-ketobutyl)-3,5-pyrazolidinedione	ChEBI
4-(3-Oxobutyl)-1,2-diphenyl-3,5-pyrazolidinedione	ChEBI
Kebuzonum	ChEBI
Ketophenylbutazonum	ChEBI
Quebuzona	ChEBI
Kebuzone	Kegg
1,2-Diphenyl-4-(g-ketobutyl)-3,5-pyrazolidinedione	Generator
1,2-Diphenyl-4-(γ-ketobutyl)-3,5-pyrazolidinedione	Generator
Chebutan	HMDB
Phloguron	HMDB
Chetofenilbutazone	HMDB
Copirene	HMDB
Racheton	HMDB
Chetofenilbutazon	HMDB
Ketazon	HMDB
Kebuzon	HMDB
Ketophenylbutazone	ChEBI

Chemical Formula

C₁₉H₁₈N₂O₃

Average Molecular Weight

322.3578

Monoisotopic Molecular Weight

322.131742452

IUPAC Name

4-(3-oxobutyl)-1,2-diphenylpyrazolidine-3,5-dione

Traditional Name

kebuzone

CAS Registry Number

853-34-9

SMILES

CC(=O)CCC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H18N2O3/c1-14(22)12-13-17-18(23)20(15-8-4-2-5-9-15)21(19(17)24)16-10-6-3-7-11-16/h2-11,17H,12-13H2,1H3

InChI Key

LGYTZKPVOAIUKX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Pyrazolidinone
1,3-dicarbonyl compound
Pyrazolidine
Carboxylic acid hydrazide
Ketone
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazolidines (CHEBI:31749 )
methyl ketone (CHEBI:31749 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041914)

Source

Exogenous

Exogenous (HMDB: HMDB0041914)

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	0.17 mg/mL at 20 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	1.99	ALOGPS
logP	2.7	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	89.37 m³·mol⁻¹	ChemAxon
Polarizability	33.64 Å³	ChemAxon
Number of Rings	3	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]+	175.891	30932474
DeepCCS	[M-H]-	173.533	30932474
DeepCCS	[M-2H]-	207.305	30932474
DeepCCS	[M+Na]+	182.535	30932474
AllCCS	[M+H]+	176.2	32859911
AllCCS	[M+H-H2O]+	173.0	32859911
AllCCS	[M+NH4]+	179.1	32859911
AllCCS	[M+Na]+	180.0	32859911
AllCCS	[M-H]-	178.2	32859911
AllCCS	[M+Na-2H]-	177.8	32859911
AllCCS	[M+HCOO]-	177.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ketophenylbutazone	CC(=O)CCC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1	3897.7	Standard polar	33892256
Ketophenylbutazone	CC(=O)CCC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1	2803.3	Standard non polar	33892256
Ketophenylbutazone	CC(=O)CCC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1	2582.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ketophenylbutazone,1TMS,isomer #1	CC(=CCC1C(=O)N(C2=CC=CC=C2)N(C2=CC=CC=C2)C1=O)O[Si](C)(C)C	2675.9	Semi standard non polar	33892256
Ketophenylbutazone,1TMS,isomer #1	CC(=CCC1C(=O)N(C2=CC=CC=C2)N(C2=CC=CC=C2)C1=O)O[Si](C)(C)C	2705.7	Standard non polar	33892256
Ketophenylbutazone,1TMS,isomer #2	C=C(CCC1C(=O)N(C2=CC=CC=C2)N(C2=CC=CC=C2)C1=O)O[Si](C)(C)C	2639.2	Semi standard non polar	33892256
Ketophenylbutazone,1TMS,isomer #2	C=C(CCC1C(=O)N(C2=CC=CC=C2)N(C2=CC=CC=C2)C1=O)O[Si](C)(C)C	2646.5	Standard non polar	33892256
Ketophenylbutazone,1TBDMS,isomer #1	CC(=CCC1C(=O)N(C2=CC=CC=C2)N(C2=CC=CC=C2)C1=O)O[Si](C)(C)C(C)(C)C	2914.4	Semi standard non polar	33892256
Ketophenylbutazone,1TBDMS,isomer #1	CC(=CCC1C(=O)N(C2=CC=CC=C2)N(C2=CC=CC=C2)C1=O)O[Si](C)(C)C(C)(C)C	2904.9	Standard non polar	33892256
Ketophenylbutazone,1TBDMS,isomer #2	C=C(CCC1C(=O)N(C2=CC=CC=C2)N(C2=CC=CC=C2)C1=O)O[Si](C)(C)C(C)(C)C	2874.1	Semi standard non polar	33892256
Ketophenylbutazone,1TBDMS,isomer #2	C=C(CCC1C(=O)N(C2=CC=CC=C2)N(C2=CC=CC=C2)C1=O)O[Si](C)(C)C(C)(C)C	2840.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ketophenylbutazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9451000000-20f6c914fed406957207	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ketophenylbutazone 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 - Ketophenylbutazone 10V, Positive-QTOF	splash10-05fr-0019000000-c5e4c3ccd5cce60874be	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketophenylbutazone 20V, Positive-QTOF	splash10-0avi-4179000000-25bd6883a89d363eb632	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketophenylbutazone 40V, Positive-QTOF	splash10-000x-9230000000-5de6d5996d83a5d16f71	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketophenylbutazone 10V, Negative-QTOF	splash10-00di-0029000000-7b443a0fcd3e3a5df407	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketophenylbutazone 20V, Negative-QTOF	splash10-0kmi-5579000000-5ea363b653693ed3125c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketophenylbutazone 40V, Negative-QTOF	splash10-0006-9500000000-706ef9e0b02460c9ff45	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketophenylbutazone 10V, Positive-QTOF	splash10-00di-0009000000-33d59492e0378fd90171	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketophenylbutazone 20V, Positive-QTOF	splash10-00di-0039000000-36491d2e363fb42d8075	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketophenylbutazone 40V, Positive-QTOF	splash10-07bf-9800000000-f0dc377845da2da2132c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketophenylbutazone 10V, Negative-QTOF	splash10-00di-0009000000-c0122f56c13f37edfeb3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketophenylbutazone 20V, Negative-QTOF	splash10-0umi-0194000000-144aa7f826627fd26805	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketophenylbutazone 40V, Negative-QTOF	splash10-053u-9200000000-9967204f9ae136396b56	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08940

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3692

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Kebuzone

METLIN ID

Not Available

PubChem Compound

3824

PDB ID

Not Available

ChEBI ID

31749

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

SIBLIKOVA O, CERNA M, HAIS IM: [Contribution to the metabolism of ketophenylbutazone. II. Ketophenylbutazone metabolites in urine]. Cesk Farm. 1962 Mar;11:123-6. [PubMed:13912486 ]
Zhivkova ZD, Russeva VN: Binding of kebuzone to human serum albumin studied by high performance liquid affinity chromatography. Arzneimittelforschung. 2000 Mar;50(3):272-5. [PubMed:10758780 ]
CUGURRA F, BRAMBILLA G: [Comparison between phenylbutazone and ketophenylbutazone]. Arch Ital Sci Farmacol. 1960 Jul;10:195-207. [PubMed:13718791 ]
SIBLIKOVA O, VACHEK J, CERNA M, TESAREK B, VITULOVA V: [Contribution to the metabolism of ketophenylbutazone. I]. Cesk Farm. 1962 Mar;11:118-23. [PubMed:13912489 ]
SALVI V: [CLINICAL EXPERIENCES WITH THE USE OF KETOPHENYLBUTAZONE]. Minerva Med. 1963 Sep 8;54:2554-6. [PubMed:14089873 ]
Horakova Z, Metys J, Cepelak V: [Influence of phenylbutazone and ketophenylbutazone on the gastrointestinal tract]. Therapie. 1965 May-Jun;20(3):617-30. [PubMed:4953937 ]
Huvar A, Sitar J, Kubistova J: [Time of onset of changes in the renographic curve following administration of ketophenylbutazone]. Vnitr Lek. 1969 Nov;15(11):1070-5. [PubMed:5364826 ]
Nielsen GH, Holmen-Christensen H: Plasma concentrations of monophenylbutazone, phenylbutazone and ketophenylbutazone after intravenous administration to rats and mice. Acta Pharmacol Toxicol (Copenh). 1967;25:Suppl 4:42. [PubMed:5630939 ]
Sitar J: [Further experiences with suppression of anginal pain with ketophenylbutazone]. Vnitr Lek. 1968 Sep;14(9):899-904. [PubMed:5680889 ]
Huvar A, Sitar J: [Effect of ketophenylbutazone on the renographic tracing examined with hippuran I-131]. Vnitr Lek. 1969 Apr;15(4):326-31. [PubMed:5780934 ]
Rejholec V: [Some new possibilities for the use of ketophenylbutazone (Ketazon-Spofa) in rheumatology]. Reumatizam. 1966;13(6):205-9. [PubMed:5973922 ]
Queisnerova M, Siblikova O, Veverkova M, Macek K, Nemecek O: [Biotransformation of ketophenylbutazone in vitro]. Cesk Farm. 1967 Jun;16(5):219-22. [PubMed:6077826 ]

Showing metabocard for Ketophenylbutazone (HMDB0041914)

MOL for HMDB0041914 (Ketophenylbutazone)

3D MOL for HMDB0041914 (Ketophenylbutazone)

3D SDF for HMDB0041914 (Ketophenylbutazone)

3D-SDF for HMDB0041914 (Ketophenylbutazone)

PDB for HMDB0041914 (Ketophenylbutazone)

3D PDB for HMDB0041914 (Ketophenylbutazone)

SMILES for HMDB0041914 (Ketophenylbutazone)

INCHI for HMDB0041914 (Ketophenylbutazone)

Structure for HMDB0041914 (Ketophenylbutazone)

3D Structure for HMDB0041914 (Ketophenylbutazone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra