Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Show more...Show more...Show more...

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-10-17 10:02:55 UTC

Update Date

2020-02-26 21:25:41 UTC

HMDB ID

HMDB0005033

Secondary Accession Numbers

HMDB05033

Metabolite Identification

Common Name

Valdecoxib

Description

Valdecoxib, also known as bextra or kudeq, belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. A former Pfizer district sales manager was indicted and sentenced to home confinement for destroying documents regarding the illegal promotion of Bextra. Valdecoxib is a drug which is used for the treatment of osteoarthritis and dysmenorrhoea. Valdecoxib is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, valdecoxib is involved in valdecoxib action pathway. Valdecoxib has analytical methods for bioequivalence studies, metabolite determination, estimation of formulation, and an HPTLC method for simultaneous estimation in tablet dosage form. Pfizer first acknowledged cardiovascular risks associated with Bextra in October 2004. and was available by prescription in tablet form until 2005 when the FDA requested that Pfizer withdraw Bextra from the American market. In the United States, the Food and Drug Administration (FDA) approved valdecoxib for the treatment of osteoarthritis, adult rheumatoid arthritis, and primary dysmenorrhea. Six whistle-blowers were awarded more than $102 million for their role in the investigation.

Structure

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

HMDB0005033
     RDKit          3D
Valdecoxib
 36 38  0  0  0  0  0  0  0  0999 V2000
    0.3170   -3.9088   -0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775   -3.0229   -0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1287   -3.4276   -0.3889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9283   -2.4261   -0.2037 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2357   -1.2824   -0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6974    0.0816    0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475    1.0437   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8794    2.3221   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680    2.6280    0.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8240    1.6565    1.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3823    0.3689    1.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974   -1.6581   -0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2546   -0.7856   -0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5808   -0.0781    0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7025    0.7373    0.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4916    0.8619   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8862    1.9064   -0.0868 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.2387    0.9805    0.4374 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308    2.9697    0.9538 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907    2.5384   -1.4215 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1789    0.1567   -1.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0693   -0.6537   -1.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330   -3.2937   -0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3170   -4.6228    0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570   -4.5133   -1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997    0.8139   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6779    3.0987   -1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9023    3.6254    0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3634    1.9471    2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5885   -0.3979    2.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0568   -0.1879    1.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9515    1.2948    1.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669    1.3371    1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9238    0.8012   -0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8320    0.2890   -2.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8324   -1.1996   -2.1679 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 17 20  2  0
 16 21  1  0
 21 22  2  0
 12  2  2  0
 22 13  1  0
 11  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 15 32  1  0
 18 33  1  0
 18 34  1  0
 21 35  1  0
 22 36  1  0
M  END

580
  Mrv0541 02231214472D          

 22 24  0  0  0  0            999 V2000
    3.1021   -1.7444    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    2.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9271   -1.7444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2771   -1.7444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146    2.8251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -2.5694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021    1.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021    0.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695    2.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    2.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -0.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    0.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876    0.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5541    1.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -0.5069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876   -0.5069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    2.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7257    0.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9518    2.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5103    0.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1234    1.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  6  1  0  0  0  0
  1 11  1  0  0  0  0
  2  5  1  0  0  0  0
  2 10  1  0  0  0  0
  5  9  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8 12  2  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 17  1  0  0  0  0
 11 15  2  0  0  0  0
 11 16  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005033

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)S(N)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20)

> <INCHI_KEY>
LNPDTQAFDNKSHK-UHFFFAOYSA-N

> <FORMULA>
C16H14N2O3S

> <MOLECULAR_WEIGHT>
314.359

> <EXACT_MASS>
314.072513014

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.76425043343251

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzene-1-sulfonamide

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
2.8236843580000004

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.057539239950927

> <JCHEM_PKA_STRONGEST_BASIC>
0.41767462897919727

> <JCHEM_POLAR_SURFACE_AREA>
86.19

> <JCHEM_REFRACTIVITY>
84.70800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
valdecoxib

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005033
     RDKit          3D
Valdecoxib
 36 38  0  0  0  0  0  0  0  0999 V2000
    0.3170   -3.9088   -0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775   -3.0229   -0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1287   -3.4276   -0.3889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9283   -2.4261   -0.2037 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2357   -1.2824   -0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6974    0.0816    0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475    1.0437   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8794    2.3221   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680    2.6280    0.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8240    1.6565    1.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3823    0.3689    1.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974   -1.6581   -0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2546   -0.7856   -0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5808   -0.0781    0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7025    0.7373    0.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4916    0.8619   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8862    1.9064   -0.0868 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.2387    0.9805    0.4374 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308    2.9697    0.9538 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907    2.5384   -1.4215 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1789    0.1567   -1.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0693   -0.6537   -1.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330   -3.2937   -0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3170   -4.6228    0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570   -4.5133   -1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997    0.8139   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6779    3.0987   -1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9023    3.6254    0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3634    1.9471    2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5885   -0.3979    2.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0568   -0.1879    1.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9515    1.2948    1.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669    1.3371    1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9238    0.8012   -0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8320    0.2890   -2.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8324   -1.1996   -2.1679 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 17 20  2  0
 16 21  1  0
 21 22  2  0
 12  2  2  0
 22 13  1  0
 11  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 15 32  1  0
 18 33  1  0
 18 34  1  0
 21 35  1  0
 22 36  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 580                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       5.791  -3.256   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       5.021   5.274   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.331  -3.256   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.251  -3.256   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       6.561   5.274   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       5.791  -4.796   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.791   2.904   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.791   1.364   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.036   3.809   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.545   3.809   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.791  -1.716   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.124   0.594   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.457   0.594   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.501   3.333   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.124  -0.946   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.457  -0.946   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080   3.333   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.645   4.364   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.821   1.827   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.110   3.888   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.286   1.351   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.430   2.381   0.000  0.00  0.00           C+0
CONECT    1    3    4    6   11                                             
CONECT    2    5   10                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    2    9                                                       
CONECT    6    1                                                            
CONECT    7    8    9   10                                                  
CONECT    8    7   12   13                                                  
CONECT    9    5    7   14                                                  
CONECT   10    2    7   17                                                  
CONECT   11    1   15   16                                                  
CONECT   12    8   15                                                       
CONECT   13    8   16                                                       
CONECT   14    9   18   19                                                  
CONECT   15   11   12                                                       
CONECT   16   11   13                                                       
CONECT   17   10                                                            
CONECT   18   14   20                                                       
CONECT   19   14   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   22                                                       
CONECT   22   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0005033
HETATM    1  C1  UNL     1       0.317  -3.909  -0.588  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.877  -3.023  -0.398  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.129  -3.428  -0.389  1.00  0.00           O  
HETATM    4  N1  UNL     1      -2.928  -2.426  -0.204  1.00  0.00           N  
HETATM    5  C3  UNL     1      -2.236  -1.282  -0.078  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.697   0.082   0.141  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.447   1.044  -0.793  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.879   2.322  -0.590  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.568   2.628   0.565  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.824   1.657   1.515  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.382   0.369   1.298  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.897  -1.658  -0.202  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.255  -0.786  -0.140  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.581  -0.078   0.990  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.702   0.737   0.967  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.492   0.862  -0.133  1.00  0.00           C  
HETATM   17  S1  UNL     1       3.886   1.906  -0.087  1.00  0.00           S  
HETATM   18  N2  UNL     1       5.239   0.980   0.437  1.00  0.00           N  
HETATM   19  O2  UNL     1       3.631   2.970   0.954  1.00  0.00           O  
HETATM   20  O3  UNL     1       4.091   2.538  -1.421  1.00  0.00           O  
HETATM   21  C15 UNL     1       2.179   0.157  -1.282  1.00  0.00           C  
HETATM   22  C16 UNL     1       1.069  -0.654  -1.269  1.00  0.00           C  
HETATM   23  H1  UNL     1       1.233  -3.294  -0.612  1.00  0.00           H  
HETATM   24  H2  UNL     1       0.317  -4.623   0.274  1.00  0.00           H  
HETATM   25  H3  UNL     1       0.157  -4.513  -1.490  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.900   0.814  -1.718  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.678   3.099  -1.344  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.902   3.625   0.718  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.363   1.947   2.394  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.589  -0.398   2.056  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.057  -0.188   1.856  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.951   1.295   1.872  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.667   1.337   1.316  1.00  0.00           H  
HETATM   34  H12 UNL     1       5.924   0.801  -0.327  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.832   0.289  -2.123  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.832  -1.200  -2.168  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   12   12
CONECT    3    4
CONECT    4    5    5
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10   28
CONECT   10   11   11   29
CONECT   11   30
CONECT   12   13
CONECT   13   14   14   22
CONECT   14   15   31
CONECT   15   16   16   32
CONECT   16   17   21
CONECT   17   18   19   19   20
CONECT   17   20
CONECT   18   33   34
CONECT   21   22   22   35
CONECT   22   36
END

HMDB0005033
     RDKit          3D
Valdecoxib
 36 38  0  0  0  0  0  0  0  0999 V2000
    0.3170   -3.9088   -0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775   -3.0229   -0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1287   -3.4276   -0.3889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9283   -2.4261   -0.2037 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2357   -1.2824   -0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6974    0.0816    0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475    1.0437   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8794    2.3221   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680    2.6280    0.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8240    1.6565    1.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3823    0.3689    1.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974   -1.6581   -0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2546   -0.7856   -0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5808   -0.0781    0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7025    0.7373    0.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4916    0.8619   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8862    1.9064   -0.0868 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.2387    0.9805    0.4374 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308    2.9697    0.9538 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907    2.5384   -1.4215 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1789    0.1567   -1.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0693   -0.6537   -1.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330   -3.2937   -0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3170   -4.6228    0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570   -4.5133   -1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997    0.8139   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6779    3.0987   -1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9023    3.6254    0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3634    1.9471    2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5885   -0.3979    2.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0568   -0.1879    1.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9515    1.2948    1.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669    1.3371    1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9238    0.8012   -0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8320    0.2890   -2.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8324   -1.1996   -2.1679 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 17 20  2  0
 16 21  1  0
 21 22  2  0
 12  2  2  0
 22 13  1  0
 11  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 15 32  1  0
 18 33  1  0
 18 34  1  0
 21 35  1  0
 22 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide	ChEBI
Bextra	ChEBI
p-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide	ChEBI
Valdecoxibum	ChEBI
4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulphonamide	Generator
p-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulphonamide	Generator
COX	HMDB
Kudeq	HMDB
Valdyn	HMDB
Valecoxib	HMDB
Pfizer brand OF valdecoxib	HMDB

Chemical Formula

C₁₆H₁₄N₂O₃S

Average Molecular Weight

314.359

Monoisotopic Molecular Weight

314.072513014

IUPAC Name

4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzene-1-sulfonamide

Traditional Name

valdecoxib

CAS Registry Number

181695-72-7

SMILES

CC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)S(N)(=O)=O

InChI Identifier

InChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20)

InChI Key

LNPDTQAFDNKSHK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
Benzenesulfonyl group
Organosulfonic acid amide
Azole
Isoxazole
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Heteroaromatic compound
Aminosulfonyl compound
Sulfonyl
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:63634 )
isoxazoles (CHEBI:63634 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0005033)
Cell membrane (HMDB: HMDB0005033)

Source

Exogenous

Exogenous (HMDB: HMDB0005033)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0005033)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Valdecoxib Action Pathway (HMDB: HMDB0005033)
Valdecoxib Action Pathway (PathBank: SMP0000116)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0005033)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	160 - 162 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.035 g/L	ALOGPS
logP	3.32	ALOGPS
logP	2.82	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	10.06	ChemAxon
pKa (Strongest Basic)	0.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.19 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.71 m³·mol⁻¹	ChemAxon
Polarizability	31.76 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
DarkChem	[M+H]+	171.102	31661259
DarkChem	[M-H]-	169.583	31661259
DeepCCS	[M+H]+	172.651	30932474
DeepCCS	[M-H]-	170.293	30932474
DeepCCS	[M-2H]-	203.689	30932474
DeepCCS	[M+Na]+	178.915	30932474
AllCCS	[M+H]+	172.9	32859911
AllCCS	[M+H-H2O]+	169.3	32859911
AllCCS	[M+NH4]+	176.2	32859911
AllCCS	[M+Na]+	177.2	32859911
AllCCS	[M-H]-	171.7	32859911
AllCCS	[M+Na-2H]-	171.1	32859911
AllCCS	[M+HCOO]-	170.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Valdecoxib	CC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)S(N)(=O)=O	4513.1	Standard polar	33892256
Valdecoxib	CC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)S(N)(=O)=O	2894.1	Standard non polar	33892256
Valdecoxib	CC1=C(C(=NO1)C1=CC=CC=C1)C1=CC=C(C=C1)S(N)(=O)=O	2954.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Valdecoxib,1TMS,isomer #1	CC1=C(C2=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C2)C(C2=CC=CC=C2)=NO1	2953.0	Semi standard non polar	33892256
Valdecoxib,1TMS,isomer #1	CC1=C(C2=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C2)C(C2=CC=CC=C2)=NO1	2784.6	Standard non polar	33892256
Valdecoxib,1TMS,isomer #1	CC1=C(C2=CC=C(S(=O)(=O)N[Si](C)(C)C)C=C2)C(C2=CC=CC=C2)=NO1	3954.0	Standard polar	33892256
Valdecoxib,2TMS,isomer #1	CC1=C(C2=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C(C2=CC=CC=C2)=NO1	2875.2	Semi standard non polar	33892256
Valdecoxib,2TMS,isomer #1	CC1=C(C2=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C(C2=CC=CC=C2)=NO1	2961.2	Standard non polar	33892256
Valdecoxib,2TMS,isomer #1	CC1=C(C2=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2)C(C2=CC=CC=C2)=NO1	3830.3	Standard polar	33892256
Valdecoxib,1TBDMS,isomer #1	CC1=C(C2=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C2)C(C2=CC=CC=C2)=NO1	3165.0	Semi standard non polar	33892256
Valdecoxib,1TBDMS,isomer #1	CC1=C(C2=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C2)C(C2=CC=CC=C2)=NO1	3024.5	Standard non polar	33892256
Valdecoxib,1TBDMS,isomer #1	CC1=C(C2=CC=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)C=C2)C(C2=CC=CC=C2)=NO1	3903.9	Standard polar	33892256
Valdecoxib,2TBDMS,isomer #1	CC1=C(C2=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C(C2=CC=CC=C2)=NO1	3362.3	Semi standard non polar	33892256
Valdecoxib,2TBDMS,isomer #1	CC1=C(C2=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C(C2=CC=CC=C2)=NO1	3406.3	Standard non polar	33892256
Valdecoxib,2TBDMS,isomer #1	CC1=C(C2=CC=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C(C2=CC=CC=C2)=NO1	3789.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Valdecoxib GC-MS (Non-derivatized) - 70eV, Positive	splash10-01qa-0290000000-adad99d8d7c023e6f63b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valdecoxib 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 - Valdecoxib LC-ESI-qTof , Positive-QTOF	splash10-0089-2930000000-dac70ddadd2ffd150b22	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valdecoxib , positive-QTOF	splash10-014i-0439000000-984ffa23e74fb8949b56	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valdecoxib , positive-QTOF	splash10-014i-0439000000-8928b5e8f850f43f1430	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valdecoxib , positive-QTOF	splash10-0089-2930000000-dac70ddadd2ffd150b22	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valdecoxib 35V, Positive-QTOF	splash10-001i-0941000000-0931692fec04d3e19f52	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valdecoxib 35V, Negative-QTOF	splash10-03di-0689000000-764e252bae3ae694704a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valdecoxib 10V, Positive-QTOF	splash10-014i-0019000000-596b73746ee066f35968	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valdecoxib 20V, Positive-QTOF	splash10-014i-0049000000-818c4a70e42df2b88f8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valdecoxib 40V, Positive-QTOF	splash10-0pbi-0390000000-13714d8251c6a02a4053	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valdecoxib 10V, Negative-QTOF	splash10-03di-0009000000-a2f711c3743b82164d6d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valdecoxib 20V, Negative-QTOF	splash10-03di-0029000000-2ac37e780c7fe646fc3e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valdecoxib 40V, Negative-QTOF	splash10-004i-9460000000-fb4b9f778483757805ea	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valdecoxib 10V, Negative-QTOF	splash10-03di-0009000000-fa0317e9dc89d23da23a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valdecoxib 20V, Negative-QTOF	splash10-03di-0009000000-fa0317e9dc89d23da23a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valdecoxib 40V, Negative-QTOF	splash10-004i-9611000000-28d2f85d0f3c715b52fa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valdecoxib 10V, Positive-QTOF	splash10-014i-0009000000-bba9fedad3067bb6377e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valdecoxib 20V, Positive-QTOF	splash10-014i-0039000000-4c17bb46a939879efeea	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valdecoxib 40V, Positive-QTOF	splash10-0a6r-2960000000-ea456b0a645f35565a29	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Valdecoxib Action Pathway		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00580

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023600

KNApSAcK ID

Not Available

Chemspider ID

106796

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Valdecoxib

METLIN ID

Not Available

PubChem Compound

119607

PDB ID

COX

ChEBI ID

63634

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Rogers, Roland S.; Talley, John J.; Brown, David L.; Nagarajan, Srinivasan; Carter, Jeffery S.; Weier, Richard M.; Stealey, Michael A.; Collins, Paul W.; Seibert, Karen; et al. Substituted isoxazoles for the treatment of inflammation. PCT Int. Appl. (1996), 171 pp. CODEN: PIXXD2 WO 9625405 A1 19960822 CAN 125:247800 AN 1996:601794

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

Enzyme Details

2. 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

Enzyme Details

3. 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

Showing metabocard for Valdecoxib (HMDB0005033)

MOL for HMDB0005033 (Valdecoxib)

3D MOL for HMDB0005033 (Valdecoxib)

3D SDF for HMDB0005033 (Valdecoxib)

3D-SDF for HMDB0005033 (Valdecoxib)

PDB for HMDB0005033 (Valdecoxib)

3D PDB for HMDB0005033 (Valdecoxib)

SMILES for HMDB0005033 (Valdecoxib)

INCHI for HMDB0005033 (Valdecoxib)

Structure for HMDB0005033 (Valdecoxib)

3D Structure for HMDB0005033 (Valdecoxib)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes