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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5)transporters (2) Show 7 proteins XML

enzymes (5)transporters (2) Show 7 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014950

Secondary Accession Numbers

HMDB14950

Metabolite Identification

Common Name

Phenylbutazone

Description

A drug that has anti-inflammatory, antipyretic, and analgesic activities. It is especially effective in the treatment of ankylosing spondylitis. It also is useful in rheumatoid arthritis and Reiter's syndrome (investigational indication). Although phenylbutazone is effective in gouty arthritis, risk/benefit considerations indicate that this drug should not be employed for this disease. (From AMA Drug Evaluations Annual, 1994, p1822)

Structure

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

HMDB0014950
     RDKit          3D
Phenylbutazone
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.6205    0.1430   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8570   -1.0936   -0.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -0.8629   -0.7846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9651   -0.5312    0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5210   -0.2537    0.8240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9987    0.9189    0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6934    1.8132   -0.4065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4363    0.7177    0.0878 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737    1.7691    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    3.0403   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9010    4.1010   -0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1963    3.8895   -0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5893    2.6405    0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6756    1.5892    0.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -0.6529    0.1925 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002   -1.3886    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6731   -1.4839   -0.9534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8376   -2.2037   -0.9487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2872   -2.8513    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5348   -2.7644    1.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793   -2.0465    1.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6301   -1.2966    0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947   -2.4639   -0.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6690    0.0607   -0.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6201    0.2619    0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1070    0.9931   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0261   -1.8860   -0.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1593   -1.5772   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1543   -0.0122   -1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9244   -1.8299   -1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3198   -1.3318    1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5388    0.3951    0.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2813   -0.1250    1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0206    3.2533   -0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6011    5.0941   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9251    4.6856   -0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6209    2.5098    0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0710    0.6674    0.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160   -0.9738   -1.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4634   -2.2999   -1.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927   -3.4213    0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8149   -3.2340    2.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7532   -1.9592    2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  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  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15 22  1  0
 22 23  2  0
 22  5  1  0
 14  9  1  0
 21 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
M  END

812
  Mrv0541 02231215012D          

 23 25  0  0  0  0            999 V2000
    3.9995    1.1186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -0.3335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -0.8184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    0.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2047    1.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146    0.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347   -0.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5402    1.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0553    2.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5541   -0.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -1.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    3.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672   -0.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -2.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7257   -1.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876   -2.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9518   -0.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -2.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5103   -1.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876   -2.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1234   -1.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -3.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2  8  2  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  3 11  1  0  0  0  0
  4  8  1  0  0  0  0
  4 12  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 11 16  1  0  0  0  0
 12 15  2  0  0  0  0
 12 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 17 21  2  0  0  0  0
 18 22  2  0  0  0  0
 19 23  2  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014950

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3

> <INCHI_KEY>
VYMDGNCVAMGZFE-UHFFFAOYSA-N

> <FORMULA>
C19H20N2O2

> <MOLECULAR_WEIGHT>
308.3743

> <EXACT_MASS>
308.152477894

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.15345474069356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-butyl-1,2-diphenylpyrazolidine-3,5-dione

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
4.135797765666666

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.1349699308593895

> <JCHEM_POLAR_SURFACE_AREA>
40.620000000000005

> <JCHEM_REFRACTIVITY>
88.75830000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
'esteve'

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014950
     RDKit          3D
Phenylbutazone
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.6205    0.1430   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8570   -1.0936   -0.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -0.8629   -0.7846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9651   -0.5312    0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5210   -0.2537    0.8240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9987    0.9189    0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6934    1.8132   -0.4065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4363    0.7177    0.0878 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737    1.7691    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    3.0403   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9010    4.1010   -0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1963    3.8895   -0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5893    2.6405    0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6756    1.5892    0.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -0.6529    0.1925 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002   -1.3886    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6731   -1.4839   -0.9534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8376   -2.2037   -0.9487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2872   -2.8513    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5348   -2.7644    1.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793   -2.0465    1.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6301   -1.2966    0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947   -2.4639   -0.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6690    0.0607   -0.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6201    0.2619    0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1070    0.9931   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0261   -1.8860   -0.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1593   -1.5772   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1543   -0.0122   -1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9244   -1.8299   -1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3198   -1.3318    1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5388    0.3951    0.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2813   -0.1250    1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0206    3.2533   -0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6011    5.0941   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9251    4.6856   -0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6209    2.5098    0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0710    0.6674    0.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160   -0.9738   -1.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4634   -2.2999   -1.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927   -3.4213    0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8149   -3.2340    2.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7532   -1.9592    2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  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  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15 22  1  0
 22 23  2  0
 22  5  1  0
 14  9  1  0
 21 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 812                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.466   2.088   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -1.098   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.036  -0.623   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       5.791  -1.528   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.021   0.842   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.115   2.088   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.561   0.842   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.545  -0.623   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.742   3.495   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.837   4.741   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.501  -1.098   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.791  -3.068   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.463   6.148   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.645  -0.068   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.124  -3.838   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.821  -2.605   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.457  -3.838   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.110  -0.544   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.124  -5.378   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.286  -3.081   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.457  -5.378   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.430  -2.050   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.791  -6.148   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    4    7   11                                                  
CONECT    4    3    8   12                                                  
CONECT    5    6    7    8                                                  
CONECT    6    5    9                                                       
CONECT    7    1    3    5                                                  
CONECT    8    2    4    5                                                  
CONECT    9    6   10                                                       
CONECT   10    9   13                                                       
CONECT   11    3   14   16                                                  
CONECT   12    4   15   17                                                  
CONECT   13   10                                                            
CONECT   14   11   18                                                       
CONECT   15   12   19                                                       
CONECT   16   11   20                                                       
CONECT   17   12   21                                                       
CONECT   18   14   22                                                       
CONECT   19   15   23                                                       
CONECT   20   16   22                                                       
CONECT   21   17   23                                                       
CONECT   22   18   20                                                       
CONECT   23   19   21                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0014950
HETATM    1  C1  UNL     1       5.620   0.143  -0.468  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.857  -1.094  -0.836  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.352  -0.863  -0.785  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.965  -0.531   0.612  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.521  -0.254   0.824  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.999   0.919   0.079  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.693   1.813  -0.406  1.00  0.00           O  
HETATM    8  N1  UNL     1      -0.436   0.718   0.088  1.00  0.00           N  
HETATM    9  C7  UNL     1      -1.374   1.769   0.030  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.997   3.040  -0.415  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.901   4.101  -0.451  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.196   3.890  -0.040  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.589   2.641   0.402  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.676   1.589   0.433  1.00  0.00           C  
HETATM   15  N2  UNL     1      -0.673  -0.653   0.192  1.00  0.00           N  
HETATM   16  C13 UNL     1      -1.900  -1.389   0.208  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.673  -1.484  -0.953  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.838  -2.204  -0.949  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.287  -2.851   0.185  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.535  -2.764   1.341  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.379  -2.047   1.323  1.00  0.00           C  
HETATM   22  C19 UNL     1       0.630  -1.297   0.256  1.00  0.00           C  
HETATM   23  O2  UNL     1       0.795  -2.464  -0.116  1.00  0.00           O  
HETATM   24  H1  UNL     1       6.669   0.061  -0.822  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.620   0.262   0.622  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.107   0.993  -1.007  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.026  -1.886  -0.035  1.00  0.00           H  
HETATM   28  H5  UNL     1       5.159  -1.577  -1.763  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.154  -0.012  -1.442  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.924  -1.830  -1.142  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.320  -1.332   1.288  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.539   0.395   0.915  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.281  -0.125   1.884  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.021   3.253  -0.742  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.601   5.094  -0.799  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.925   4.686  -0.043  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.621   2.510   0.720  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.071   0.667   0.798  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.316  -0.974  -1.833  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.463  -2.300  -1.846  1.00  0.00           H  
HETATM   41  H18 UNL     1      -5.193  -3.421   0.217  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.815  -3.234   2.253  1.00  0.00           H  
HETATM   43  H20 UNL     1      -1.753  -1.959   2.225  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   22   33
CONECT    6    7    7    8
CONECT    8    9   15
CONECT    9   10   10   14
CONECT   10   11   34
CONECT   11   12   12   35
CONECT   12   13   36
CONECT   13   14   14   37
CONECT   14   38
CONECT   15   16   22
CONECT   16   17   17   21
CONECT   17   18   39
CONECT   18   19   19   40
CONECT   19   20   41
CONECT   20   21   21   42
CONECT   21   43
CONECT   22   23   23
END

HMDB0014950
     RDKit          3D
Phenylbutazone
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.6205    0.1430   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8570   -1.0936   -0.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -0.8629   -0.7846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9651   -0.5312    0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5210   -0.2537    0.8240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9987    0.9189    0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6934    1.8132   -0.4065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4363    0.7177    0.0878 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737    1.7691    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    3.0403   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9010    4.1010   -0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1963    3.8895   -0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5893    2.6405    0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6756    1.5892    0.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -0.6529    0.1925 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002   -1.3886    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6731   -1.4839   -0.9534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8376   -2.2037   -0.9487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2872   -2.8513    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5348   -2.7644    1.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793   -2.0465    1.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6301   -1.2966    0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947   -2.4639   -0.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6690    0.0607   -0.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6201    0.2619    0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1070    0.9931   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0261   -1.8860   -0.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1593   -1.5772   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1543   -0.0122   -1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9244   -1.8299   -1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3198   -1.3318    1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5388    0.3951    0.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2813   -0.1250    1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0206    3.2533   -0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6011    5.0941   -0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9251    4.6856   -0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6209    2.5098    0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0710    0.6674    0.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160   -0.9738   -1.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4634   -2.2999   -1.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927   -3.4213    0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8149   -3.2340    2.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7532   -1.9592    2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  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  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15 22  1  0
 22 23  2  0
 22  5  1  0
 14  9  1  0
 21 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,5-Dioxo-1,2-diphenyl-4-N-butylpyrazolidine	ChEBI
4-BUTYL-1,2-diphenyl-pyrazolidine-3,5-dione	ChEBI
4-N-Butyl-1,2-diphenyl-3,5-pyrazolidinedione	ChEBI
Fenilbutazona	ChEBI
Phenbutazone	ChEBI
Phenylbutazon	ChEBI
Phenylbutazonum	ChEBI
Azolid	Kegg
Butacote	HMDB
Butapirazol	HMDB
Fenilbutazon	HMDB
Butadion	HMDB
Butadione	HMDB
Butapyrazole	HMDB
Butazolidin	HMDB
Diphenylbutazone	HMDB

Chemical Formula

C₁₉H₂₀N₂O₂

Average Molecular Weight

308.3743

Monoisotopic Molecular Weight

308.152477894

IUPAC Name

4-butyl-1,2-diphenylpyrazolidine-3,5-dione

Traditional Name

'esteve'

CAS Registry Number

50-33-9

SMILES

CCCCC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3

InChI Key

VYMDGNCVAMGZFE-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
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazolidines (CHEBI:48574 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014950)
Membrane (HMDB: HMDB0014950)

Source

Exogenous

Exogenous (HMDB: HMDB0014950)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Phenylbutazone Action Pathway (PathBank: SMP0000701)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	105 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.14 g/L	Not Available
LogP	3.7	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	172.447	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000761

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.81	ALOGPS
logP	4.14	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	5.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.62 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	88.76 m³·mol⁻¹	ChemAxon
Polarizability	34.15 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]+	182.411	30932474
DeepCCS	[M-H]-	180.053	30932474
DeepCCS	[M-2H]-	213.558	30932474
DeepCCS	[M+Na]+	188.976	30932474
AllCCS	[M+H]+	174.3	32859911
AllCCS	[M+H-H2O]+	171.0	32859911
AllCCS	[M+NH4]+	177.3	32859911
AllCCS	[M+Na]+	178.2	32859911
AllCCS	[M-H]-	176.6	32859911
AllCCS	[M+Na-2H]-	176.3	32859911
AllCCS	[M+HCOO]-	176.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylbutazone	CCCCC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1	3627.5	Standard polar	33892256
Phenylbutazone	CCCCC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1	2624.5	Standard non polar	33892256
Phenylbutazone	CCCCC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1	2408.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylbutazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-005c-9450000000-4ff37844132da56b866e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylbutazone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylbutazone 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 - Phenylbutazone LC-ESI-QFT , negative-QTOF	splash10-0a4i-0009000000-f8e4cda83d45cc4ca59b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QFT , negative-QTOF	splash10-0a4i-0549000000-2907029e48d9c65ae00e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QFT , negative-QTOF	splash10-001i-2910000000-bb1ac78907a0338c7dc6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QFT , negative-QTOF	splash10-000x-6900000000-4f14a2268cc3ae06d3e5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QFT , negative-QTOF	splash10-0006-9400000000-d5012ae523568dc8e63c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QFT , negative-QTOF	splash10-0006-9100000000-2af914d40adc6817f026	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QFT , negative-QTOF	splash10-0006-9000000000-1b11164dde00c44d0ffe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QFT , negative-QTOF	splash10-0006-9000000000-3b304315d58e9e8f6984	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QFT , negative-QTOF	splash10-00kf-9000000000-b6387c41c12a5abb6d4b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0009000000-bde0ac035aafd4e337f2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QTOF , positive-QTOF	splash10-0006-0092000000-e77e2c9ca9127d3ecff9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QTOF , positive-QTOF	splash10-0a4l-0196000000-6d31987fe09f0949a98d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QTOF , positive-QTOF	splash10-016r-0190000000-6b839462a4e745d1fc0d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QTOF , positive-QTOF	splash10-00vi-0290000000-c78339fd5994808afb08	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QFT , positive-QTOF	splash10-0a4i-0109000000-c3cb4b19bc15bf87c709	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QFT , positive-QTOF	splash10-03kl-2921000000-02a08606b3d2e3c8c702	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QFT , positive-QTOF	splash10-01vo-5910000000-1e1a7cd346204d8387aa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QFT , positive-QTOF	splash10-0006-9700000000-b87550cf5df8c862c64a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylbutazone LC-ESI-QFT , positive-QTOF	splash10-00kf-9500000000-222c301c8bf7fa8c9490	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylbutazone 10V, Positive-QTOF	splash10-0a4i-1109000000-afb5ea69eff4404428be	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylbutazone 20V, Positive-QTOF	splash10-0aou-9276000000-d9698fa12a608213d596	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylbutazone 40V, Positive-QTOF	splash10-0006-9110000000-43fc2f7c8c7d34d3c784	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylbutazone 10V, Negative-QTOF	splash10-0a4i-0119000000-bae6357c0badde196104	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylbutazone 20V, Negative-QTOF	splash10-0a4i-6669000000-1cf1313cd0d66117dd0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylbutazone 40V, Negative-QTOF	splash10-0006-9300000000-6a338e07dc558445ef7d	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Phenylbutazone Action Pathway		Not Available

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 DB00812	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00812	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00812

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4617

KEGG Compound ID

C07440

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenylbutazone

METLIN ID

Not Available

PubChem Compound

4781

PDB ID

P1Z

ChEBI ID

48574

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

Not Available

Enzymes

Enzyme Details

1. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Arifah AK, Lees P: Pharmacodynamics and pharmacokinetics of phenylbutazone in calves. J Vet Pharmacol Ther. 2002 Aug;25(4):299-309. [PubMed:12213119 ]
Takada Y, Bhardwaj A, Potdar P, Aggarwal BB: Nonsteroidal anti-inflammatory agents differ in their ability to suppress NF-kappaB activation, inhibition of expression of cyclooxygenase-2 and cyclin D1, and abrogation of tumor cell proliferation. Oncogene. 2004 Dec 9;23(57):9247-58. [PubMed:15489888 ]
Beretta C, Garavaglia G, Cavalli M: COX-1 and COX-2 inhibition in horse blood by phenylbutazone, flunixin, carprofen and meloxicam: an in vitro analysis. Pharmacol Res. 2005 Oct;52(4):302-6. [PubMed:15939622 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Zitova A, Hynes J, Kollar J, Borisov SM, Klimant I, Papkovsky DB: Analysis of activity and inhibition of oxygen-dependent enzymes by optical respirometry on the LightCycler system. Anal Biochem. 2010 Feb 15;397(2):144-51. doi: 10.1016/j.ab.2009.10.029. Epub 2009 Oct 20. [PubMed:19849999 ]
Beretta C, Garavaglia G, Cavalli M: COX-1 and COX-2 inhibition in horse blood by phenylbutazone, flunixin, carprofen and meloxicam: an in vitro analysis. Pharmacol Res. 2005 Oct;52(4):302-6. [PubMed:15939622 ]
Morton AJ, Campbell NB, Gayle JM, Redding WR, Blikslager AT: Preferential and non-selective cyclooxygenase inhibitors reduce inflammation during lipopolysaccharide-induced synovitis. Res Vet Sci. 2005 Apr;78(2):189-92. [PubMed:15563928 ]

Enzyme Details

3. 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

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. 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

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Prostacyclin synthase

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
Gene Name:: PTGIS
Uniprot ID:: Q16647
Molecular weight:: 57103.385

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Reed GA, Griffin IO, Eling TE: Inactivation of prostaglandin H synthase and prostacyclin synthase by phenylbutazone. Requirement for peroxidative metabolism. Mol Pharmacol. 1985 Jan;27(1):109-14. [PubMed:3917545 ]
Marnett LJ, Siedlik PH, Ochs RC, Pagels WR, Das M, Honn KV, Warnock RH, Tainer BE, Eling TE: Mechanism of the stimulation of prostaglandin H synthase and prostacyclin synthase by the antithrombotic and antimetastatic agent, nafazatrom. Mol Pharmacol. 1984 Sep;26(2):328-35. [PubMed:6434940 ]
Tobin T, Chay S, Kamerling S, Woods WE, Weckman TJ, Blake JW, Lees P: Phenylbutazone in the horse: a review. J Vet Pharmacol Ther. 1986 Mar;9(1):1-25. [PubMed:3517382 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 11

General function:: Involved in transporter activity
Specific function:: Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:: SLC22A11
Uniprot ID:: Q9NSA0
Molecular weight:: 59970.9

References

Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]

Enzyme Details

2. 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

Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]
Uwai Y, Saito H, Inui K: Interaction between methotrexate and nonsteroidal anti-inflammatory drugs in organic anion transporter. Eur J Pharmacol. 2000 Dec 1;409(1):31-6. [PubMed:11099697 ]
Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563 ]

Showing metabocard for Phenylbutazone (HMDB0014950)

MOL for HMDB0014950 (Phenylbutazone)

3D MOL for HMDB0014950 (Phenylbutazone)

3D SDF for HMDB0014950 (Phenylbutazone)

3D-SDF for HMDB0014950 (Phenylbutazone)

PDB for HMDB0014950 (Phenylbutazone)

3D PDB for HMDB0014950 (Phenylbutazone)

SMILES for HMDB0014950 (Phenylbutazone)

INCHI for HMDB0014950 (Phenylbutazone)

Structure for HMDB0014950 (Phenylbutazone)

3D Structure for HMDB0014950 (Phenylbutazone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

Transporters

References

References