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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:16:29 UTC

Update Date

2021-09-26 23:11:23 UTC

HMDB ID

HMDB0256021

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Oxyphenbutazone

Description

Oxyphenbutazone, also known as oxi-fenibutol or oxifenbutazona, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Oxyphenbutazone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Oxyphenbutazone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Oxyphenbutazone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Oxyphenbutazone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0256021
     RDKit          3D
Oxyphenbutazone
 44 46  0  0  0  0  0  0  0  0999 V2000
    5.8624   -2.2360   -0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0937   -1.1110   -0.9873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8535   -0.8576   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0134    0.2415   -0.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000    0.4630    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9617    1.5658   -0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3718    2.6549   -0.8826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3929    1.2214   -0.1774 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5238    2.1165   -0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312    1.9262   -1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4864    2.7936   -1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6787    3.8640   -0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7694    4.0622    0.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7169    3.1832    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479   -0.1175    0.1865 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6089   -0.8920    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7199   -2.1758   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8226   -2.9612    0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8365   -2.4767    0.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9367   -3.3053    1.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7255   -1.2043    1.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6244   -0.3959    1.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8703   -0.6575    0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1865   -1.8781    0.3583 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3754   -3.2254   -0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920   -2.2363   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8547   -2.1309    0.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6877   -0.2108   -1.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772   -1.5138   -1.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1850   -0.5951    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3682   -1.8401   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7130   -0.0240   -1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5620    1.2151   -0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1796    0.7974    1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103    1.1138   -2.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2392    2.6975   -2.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5401    4.5414   -0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9243    4.9103    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112    3.3614    1.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958   -2.5395   -0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8811   -3.9690   -0.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9731   -3.9453    1.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5390   -0.8478    2.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5721    0.6175    1.6841 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
 19 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  2  0
 23  5  1  0
 14  9  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
M  END

3585
  Mrv0541 02231217022D          

 24 26  0  0  1  0            999 V2000
    1.6500   -0.0480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9995    1.6590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -3.5780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -0.2780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695    0.2069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    0.9916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2047    1.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146    0.9916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5402    2.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0553    3.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -1.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5541   -0.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    3.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -1.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876   -1.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7257   -0.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -2.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876   -2.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9518    0.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5103   -1.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -2.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1234   -0.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  2  0  0  0  0
  2  9  2  0  0  0  0
  3 23  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4 12  1  0  0  0  0
  5  9  1  0  0  0  0
  5 13  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  2  0  0  0  0
 12 16  1  0  0  0  0
 13 17  2  0  0  0  0
 13 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 17 21  1  0  0  0  0
 18 22  2  0  0  0  0
 19 23  2  0  0  0  0
 20 23  1  0  0  0  0
 21 24  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256021

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H20N2O3/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15/h4-8,10-13,17,22H,2-3,9H2,1H3

> <INCHI_KEY>
HFHZKZSRXITVMK-UHFFFAOYSA-N

> <FORMULA>
C19H20N2O3

> <MOLECULAR_WEIGHT>
324.3737

> <EXACT_MASS>
324.147392516

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.14453215698653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
3.8322324440000006

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.28657300059134

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.8666588523311844

> <JCHEM_PKA_STRONGEST_BASIC>
-5.968036895068672

> <JCHEM_POLAR_SURFACE_AREA>
60.85000000000001

> <JCHEM_REFRACTIVITY>
90.73920000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.56e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxyphenbutazone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256021
     RDKit          3D
Oxyphenbutazone
 44 46  0  0  0  0  0  0  0  0999 V2000
    5.8624   -2.2360   -0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0937   -1.1110   -0.9873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8535   -0.8576   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0134    0.2415   -0.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000    0.4630    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9617    1.5658   -0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3718    2.6549   -0.8826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3929    1.2214   -0.1774 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5238    2.1165   -0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312    1.9262   -1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4864    2.7936   -1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6787    3.8640   -0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7694    4.0622    0.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7169    3.1832    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479   -0.1175    0.1865 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6089   -0.8920    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7199   -2.1758   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8226   -2.9612    0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8365   -2.4767    0.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9367   -3.3053    1.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7255   -1.2043    1.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6244   -0.3959    1.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8703   -0.6575    0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1865   -1.8781    0.3583 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3754   -3.2254   -0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920   -2.2363   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8547   -2.1309    0.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6877   -0.2108   -1.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772   -1.5138   -1.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1850   -0.5951    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3682   -1.8401   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7130   -0.0240   -1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5620    1.2151   -0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1796    0.7974    1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103    1.1138   -2.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2392    2.6975   -2.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5401    4.5414   -0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9243    4.9103    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112    3.3614    1.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958   -2.5395   -0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8811   -3.9690   -0.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9731   -3.9453    1.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5390   -0.8478    2.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5721    0.6175    1.6841 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
 19 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  2  0
 23  5  1  0
 14  9  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3585                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080  -0.090   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.466   3.097   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.791  -6.679   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       5.791  -0.519   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.036   0.386   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.021   1.851   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.115   3.097   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.545   0.386   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.561   1.851   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.742   4.504   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.837   5.750   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.791  -2.059   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.501  -0.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.463   7.156   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.124  -2.829   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.457  -2.829   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.645   0.941   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.821  -1.596   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.124  -4.369   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.457  -4.369   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.110   0.465   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.286  -2.072   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.791  -5.139   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.430  -1.041   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   23                                                            
CONECT    4    5    8   12                                                  
CONECT    5    4    9   13                                                  
CONECT    6    7    8    9                                                  
CONECT    7    6   10                                                       
CONECT    8    1    4    6                                                  
CONECT    9    2    5    6                                                  
CONECT   10    7   11                                                       
CONECT   11   10   14                                                       
CONECT   12    4   15   16                                                  
CONECT   13    5   17   18                                                  
CONECT   14   11                                                            
CONECT   15   12   19                                                       
CONECT   16   12   20                                                       
CONECT   17   13   21                                                       
CONECT   18   13   22                                                       
CONECT   19   15   23                                                       
CONECT   20   16   23                                                       
CONECT   21   17   24                                                       
CONECT   22   18   24                                                       
CONECT   23    3   19   20                                                  
CONECT   24   21   22                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0256021
HETATM    1  C1  UNL     1       5.862  -2.236  -0.331  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.094  -1.111  -0.987  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.853  -0.858  -0.129  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.013   0.242  -0.693  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.800   0.463   0.173  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.962   1.566  -0.353  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.372   2.655  -0.883  1.00  0.00           O  
HETATM    8  N1  UNL     1      -0.393   1.221  -0.177  1.00  0.00           N  
HETATM    9  C7  UNL     1      -1.524   2.116  -0.351  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.431   1.926  -1.360  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.486   2.794  -1.486  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.679   3.864  -0.631  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.769   4.062   0.387  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.717   3.183   0.499  1.00  0.00           C  
HETATM   15  N2  UNL     1      -0.448  -0.118   0.186  1.00  0.00           N  
HETATM   16  C13 UNL     1      -1.609  -0.892   0.462  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.720  -2.176  -0.070  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.823  -2.961   0.173  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.836  -2.477   0.954  1.00  0.00           C  
HETATM   20  O2  UNL     1      -4.937  -3.305   1.176  1.00  0.00           O  
HETATM   21  C17 UNL     1      -3.725  -1.204   1.480  1.00  0.00           C  
HETATM   22  C18 UNL     1      -2.624  -0.396   1.248  1.00  0.00           C  
HETATM   23  C19 UNL     1       0.870  -0.657   0.252  1.00  0.00           C  
HETATM   24  O3  UNL     1       1.186  -1.878   0.358  1.00  0.00           O  
HETATM   25  H1  UNL     1       5.375  -3.225  -0.525  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.892  -2.236  -0.701  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.855  -2.131   0.780  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.688  -0.211  -1.150  1.00  0.00           H  
HETATM   29  H5  UNL     1       4.777  -1.514  -1.994  1.00  0.00           H  
HETATM   30  H6  UNL     1       4.185  -0.595   0.916  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.368  -1.840  -0.038  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.713  -0.024  -1.738  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.562   1.215  -0.691  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.180   0.797   1.168  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.310   1.114  -2.033  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.239   2.698  -2.264  1.00  0.00           H  
HETATM   37  H13 UNL     1      -4.540   4.541  -0.763  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.924   4.910   1.060  1.00  0.00           H  
HETATM   39  H15 UNL     1      -1.011   3.361   1.313  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.896  -2.539  -0.689  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.881  -3.969  -0.259  1.00  0.00           H  
HETATM   42  H18 UNL     1      -4.973  -3.945   1.962  1.00  0.00           H  
HETATM   43  H19 UNL     1      -4.539  -0.848   2.092  1.00  0.00           H  
HETATM   44  H20 UNL     1      -2.572   0.618   1.684  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   23   34
CONECT    6    7    7    8
CONECT    8    9   15
CONECT    9   10   10   14
CONECT   10   11   35
CONECT   11   12   12   36
CONECT   12   13   37
CONECT   13   14   14   38
CONECT   14   39
CONECT   15   16   23
CONECT   16   17   17   22
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   19   20   21
CONECT   20   42
CONECT   21   22   22   43
CONECT   22   44
CONECT   23   24   24
END

HMDB0256021
     RDKit          3D
Oxyphenbutazone
 44 46  0  0  0  0  0  0  0  0999 V2000
    5.8624   -2.2360   -0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0937   -1.1110   -0.9873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8535   -0.8576   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0134    0.2415   -0.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000    0.4630    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9617    1.5658   -0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3718    2.6549   -0.8826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3929    1.2214   -0.1774 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5238    2.1165   -0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312    1.9262   -1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4864    2.7936   -1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6787    3.8640   -0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7694    4.0622    0.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7169    3.1832    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479   -0.1175    0.1865 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6089   -0.8920    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7199   -2.1758   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8226   -2.9612    0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8365   -2.4767    0.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9367   -3.3053    1.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7255   -1.2043    1.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6244   -0.3959    1.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8703   -0.6575    0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1865   -1.8781    0.3583 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3754   -3.2254   -0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920   -2.2363   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8547   -2.1309    0.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6877   -0.2108   -1.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772   -1.5138   -1.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1850   -0.5951    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3682   -1.8401   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7130   -0.0240   -1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5620    1.2151   -0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1796    0.7974    1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103    1.1138   -2.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2392    2.6975   -2.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5401    4.5414   -0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9243    4.9103    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112    3.3614    1.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958   -2.5395   -0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8811   -3.9690   -0.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9731   -3.9453    1.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5390   -0.8478    2.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5721    0.6175    1.6841 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
 19 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  2  0
 23  5  1  0
 14  9  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(p-Hydroxyphenyl)-2-phenyl-4-butyl-3,5-pyrazolidinedione	ChEBI
1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-butylpyrazolidine	ChEBI
1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-N-butylpyrazolidine	ChEBI
3,5-Dioxo-1-phenyl-2-(p-hydroxyphenyl)-4-N-butylpyrazolidene	ChEBI
4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione	ChEBI
4-Butyl-1-(p-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione	ChEBI
4-Butyl-2-(4-hydroxyphenyl)-1-phenyl-3,5-dioxopyrazolidine	ChEBI
4-Butyl-2-(p-hydroxyphenyl)-1-phenyl-3,5-pyrazolidinedione	ChEBI
Hydroxyphenylbutazon	ChEBI
Oxi-fenibutol	ChEBI
Oxifenbutazona	ChEBI
Oxifenylbutazon	ChEBI
Oxiphenbutazonum	ChEBI
Oxyphenbutazonum	ChEBI
Oxyphenylbutazone	ChEBI
p-Hydroxyphenylbutazone	ChEBI
p-Oxyphenylbutazone	ChEBI
Reozon	Kegg
Tanderil	MeSH
Belmac brand OF oxyphenbutazone	MeSH
Diflamil	MeSH
Hydroxyphenylbutazone	MeSH
Novartis ophthalmics brand OF oxyphenbutazone	MeSH

Chemical Formula

C₁₉H₂₀N₂O₃

Average Molecular Weight

324.3737

Monoisotopic Molecular Weight

324.147392516

IUPAC Name

4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione

Traditional Name

oxyphenbutazone

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H20N2O3/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15/h4-8,10-13,17,22H,2-3,9H2,1H3

InChI Key

HFHZKZSRXITVMK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
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

phenols (CHEBI:76258 )
pyrazolidines (CHEBI:76258 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0256021)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.79	ALOGPS
logP	3.83	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.87	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.85 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	90.74 m³·mol⁻¹	ChemAxon
Polarizability	35.14 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]+	189.149	30932474
DeepCCS	[M-H]-	186.639	30932474
DeepCCS	[M-2H]-	221.264	30932474
DeepCCS	[M+Na]+	197.554	30932474
AllCCS	[M+H]+	177.7	32859911
AllCCS	[M+H-H2O]+	174.6	32859911
AllCCS	[M+NH4]+	180.6	32859911
AllCCS	[M+Na]+	181.4	32859911
AllCCS	[M-H]-	178.8	32859911
AllCCS	[M+Na-2H]-	178.5	32859911
AllCCS	[M+HCOO]-	178.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	18.1442 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.54 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3120.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	482.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	211.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	239.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	492.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	813.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	700.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	75.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1616.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	563.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1787.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	516.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	456.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	379.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	174.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	19.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oxyphenbutazone	CCCCC1C(=O)N(N(C1=O)C1=CC=C(O)C=C1)C1=CC=CC=C1	3912.1	Standard polar	33892256
Oxyphenbutazone	CCCCC1C(=O)N(N(C1=O)C1=CC=C(O)C=C1)C1=CC=CC=C1	2929.4	Standard non polar	33892256
Oxyphenbutazone	CCCCC1C(=O)N(N(C1=O)C1=CC=C(O)C=C1)C1=CC=CC=C1	2770.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Oxyphenbutazone EI-B (Non-derivatized)	splash10-0006-9601000000-0e93b2309b6f4ff21792	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxyphenbutazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-054k-8791000000-637b7e1dbae4d383b921	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxyphenbutazone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxyphenbutazone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxyphenbutazone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxyphenbutazone , positive-QTOF	splash10-0002-3920000000-8a5be556648d9ff3213b	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxyphenbutazone 10V, Positive-QTOF	splash10-004i-1129000000-635a75af02145840f4c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxyphenbutazone 20V, Positive-QTOF	splash10-004i-7396000000-7af7a18b0ccfe9a692b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxyphenbutazone 40V, Positive-QTOF	splash10-00kf-9300000000-beaa3a49e9b7a30e7df1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxyphenbutazone 10V, Negative-QTOF	splash10-00di-0119000000-982c7f5b104baf102d43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxyphenbutazone 20V, Negative-QTOF	splash10-00dj-6698000000-2933626114d1b33aada5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxyphenbutazone 40V, Negative-QTOF	splash10-0a4p-7900000000-77b1ac23e35e6cb8ed59	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03585

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4480

KEGG Compound ID

C19494

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxyphenbutazone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

76258

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Oxyphenbutazone (HMDB0256021)

MOL for HMDB0256021 (Oxyphenbutazone)

3D MOL for HMDB0256021 (Oxyphenbutazone)

3D SDF for HMDB0256021 (Oxyphenbutazone)

3D-SDF for HMDB0256021 (Oxyphenbutazone)

PDB for HMDB0256021 (Oxyphenbutazone)

3D PDB for HMDB0256021 (Oxyphenbutazone)

SMILES for HMDB0256021 (Oxyphenbutazone)

INCHI for HMDB0256021 (Oxyphenbutazone)

Structure for HMDB0256021 (Oxyphenbutazone)

3D Structure for HMDB0256021 (Oxyphenbutazone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra