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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (2) Show 6 proteins XML

enzymes (4)transporters (2) Show 6 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:01:06 UTC

Update Date

2020-02-26 21:39:23 UTC

HMDB ID

HMDB0014096

Secondary Accession Numbers

HMDB14096

Metabolite Identification

Common Name

5'-Hydroxypiroxicam

Description

5'-Hydroxypiroxicam is only found in individuals that have used or taken Piroxicam. 5'-Hydroxypiroxicam is a metabolite of Piroxicam. 5'-hydroxypiroxicam belongs to the family of Benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-member ring with four carbon atoms, one nitrogen atom and one sulfur atom).

Structure

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

HMDB0014096
     RDKit          3D
5'-Hydroxypiroxicam
 37 39  0  0  0  0  0  0  0  0999 V2000
   -0.7263   -0.2247   -2.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3509   -0.3473   -1.6795 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -0.1140   -0.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8118   -0.0569   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864   -0.2226   -1.6968 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6745    0.1525    0.5555 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0815    0.1945    0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8038    0.0458   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2101    0.1029   -0.7604 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8903    0.3173    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2942    0.3882    0.4459 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1616    0.4673    1.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    0.4086    1.5540 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3151    0.0310    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5805    0.2678    1.8459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7679   -0.0464    0.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3052    0.2397    2.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6472    0.2716    2.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5227    0.0165    1.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0059   -0.2666    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6589   -0.2976   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0175   -0.7621   -1.6756 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.7785   -0.0516   -2.7543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2081   -2.2661   -1.7843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5327   -0.1525   -3.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    0.7258   -3.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276   -1.1147   -3.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393    0.2954    1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3137   -0.1262   -1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7402   -0.0208   -1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7473    1.2936    0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7491    0.6390    2.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6950   -0.2983    2.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5945    0.4414    2.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0280    0.5002    3.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5869    0.0403    1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6703   -0.4711   -0.7265 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  3 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  2  0
 22  2  1  0
 13  7  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
M  END


  Mrv0541 06191310522D          

 24 26  0  0  0  0            999 V2000
    6.9313   -4.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2169   -3.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5024   -4.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5024   -5.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2169   -5.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9313   -5.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6458   -5.5932    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.3603   -5.1807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3603   -4.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6458   -3.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0747   -3.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0747   -3.1183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7891   -2.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5036   -1.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7891   -1.8808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5036   -3.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2181   -2.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2181   -1.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0747   -5.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6458   -3.1183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7892   -4.3558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0624   -6.1766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -6.1766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9326   -1.4684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 15 13  2  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 14 18  2  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  8 19  1  0  0  0  0
 10 20  1  0  0  0  0
 11 21  2  0  0  0  0
  7 22  2  0  0  0  0
  7 23  2  0  0  0  0
 18 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014096

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(C(=O)NC2=NC=C(O)C=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H13N3O5S/c1-18-13(15(21)17-12-7-6-9(19)8-16-12)14(20)10-4-2-3-5-11(10)24(18,22)23/h2-8,19-20H,1H3,(H,16,17,21)

> <INCHI_KEY>
CCKOORANQAQKKV-UHFFFAOYSA-N

> <FORMULA>
C15H13N3O5S

> <MOLECULAR_WEIGHT>
347.346

> <EXACT_MASS>
347.057591231

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.287314152839556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-N-(5-hydroxypyridin-2-yl)-2-methyl-1,1-dioxo-2H-1λ⁶,2-benzothiazine-3-carboxamide

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
0.2990436988655614

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.722520689983673

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.655515341949981

> <JCHEM_PKA_STRONGEST_BASIC>
3.719231090225203

> <JCHEM_POLAR_SURFACE_AREA>
119.83

> <JCHEM_REFRACTIVITY>
89.0244

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-N-(5-hydroxypyridin-2-yl)-2-methyl-1,1-dioxo-1λ⁶,2-benzothiazine-3-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014096
     RDKit          3D
5'-Hydroxypiroxicam
 37 39  0  0  0  0  0  0  0  0999 V2000
   -0.7263   -0.2247   -2.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3509   -0.3473   -1.6795 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -0.1140   -0.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8118   -0.0569   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864   -0.2226   -1.6968 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6745    0.1525    0.5555 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0815    0.1945    0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8038    0.0458   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2101    0.1029   -0.7604 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8903    0.3173    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2942    0.3882    0.4459 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1616    0.4673    1.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    0.4086    1.5540 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3151    0.0310    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5805    0.2678    1.8459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7679   -0.0464    0.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3052    0.2397    2.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6472    0.2716    2.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5227    0.0165    1.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0059   -0.2666    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6589   -0.2976   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0175   -0.7621   -1.6756 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.7785   -0.0516   -2.7543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2081   -2.2661   -1.7843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5327   -0.1525   -3.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    0.7258   -3.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276   -1.1147   -3.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393    0.2954    1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3137   -0.1262   -1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7402   -0.0208   -1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7473    1.2936    0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7491    0.6390    2.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6950   -0.2983    2.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5945    0.4414    2.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0280    0.5002    3.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5869    0.0403    1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6703   -0.4711   -0.7265 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  3 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  2  0
 22  2  1  0
 13  7  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
M  END

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1  C   UNK     0      12.938  -8.131   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.605  -7.361   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.271  -8.131   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.271  -9.671   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.605 -10.441   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.938  -9.671   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      14.272 -10.441   0.000  0.00  0.00           S+0
HETATM    8  N   UNK     0      15.606  -9.671   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      15.606  -8.131   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.272  -7.361   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.940  -7.361   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      16.940  -5.821   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      18.273  -5.051   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.607  -2.741   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      18.273  -3.511   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      19.607  -5.821   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.940  -5.051   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.940  -3.511   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.940 -10.441   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.272  -5.821   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      18.273  -8.131   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      13.183 -11.530   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      15.361 -11.530   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      22.274  -2.741   0.000  0.00  0.00           O+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8   22   23                                             
CONECT    8    7    9   19                                                  
CONECT    9    8   10   11                                                  
CONECT   10    1    9   20                                                  
CONECT   11    9   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   15   16                                                  
CONECT   14   15   18                                                       
CONECT   15   13   14                                                       
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   14   17   24                                                  
CONECT   19    8                                                            
CONECT   20   10                                                            
CONECT   21   11                                                            
CONECT   22    7                                                            
CONECT   23    7                                                            
CONECT   24   18                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0014096
HETATM    1  C1  UNL     1      -0.726  -0.225  -2.975  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.351  -0.347  -1.679  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.671  -0.114  -0.451  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.812  -0.057  -0.517  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.286  -0.223  -1.697  1.00  0.00           O  
HETATM    6  N2  UNL     1       1.675   0.153   0.556  1.00  0.00           N  
HETATM    7  C4  UNL     1       3.082   0.194   0.419  1.00  0.00           C  
HETATM    8  C5  UNL     1       3.804   0.046  -0.722  1.00  0.00           C  
HETATM    9  C6  UNL     1       5.210   0.103  -0.760  1.00  0.00           C  
HETATM   10  C7  UNL     1       5.890   0.317   0.397  1.00  0.00           C  
HETATM   11  O2  UNL     1       7.294   0.388   0.446  1.00  0.00           O  
HETATM   12  C8  UNL     1       5.162   0.467   1.548  1.00  0.00           C  
HETATM   13  N3  UNL     1       3.837   0.409   1.554  1.00  0.00           N  
HETATM   14  C9  UNL     1      -1.315   0.031   0.692  1.00  0.00           C  
HETATM   15  O3  UNL     1      -0.580   0.268   1.846  1.00  0.00           O  
HETATM   16  C10 UNL     1      -2.768  -0.046   0.885  1.00  0.00           C  
HETATM   17  C11 UNL     1      -3.305   0.240   2.151  1.00  0.00           C  
HETATM   18  C12 UNL     1      -4.647   0.272   2.382  1.00  0.00           C  
HETATM   19  C13 UNL     1      -5.523   0.016   1.348  1.00  0.00           C  
HETATM   20  C14 UNL     1      -5.006  -0.267   0.104  1.00  0.00           C  
HETATM   21  C15 UNL     1      -3.659  -0.298  -0.117  1.00  0.00           C  
HETATM   22  S1  UNL     1      -3.018  -0.762  -1.676  1.00  0.00           S  
HETATM   23  O4  UNL     1      -3.778  -0.052  -2.754  1.00  0.00           O  
HETATM   24  O5  UNL     1      -3.208  -2.266  -1.784  1.00  0.00           O  
HETATM   25  H1  UNL     1      -1.533  -0.153  -3.764  1.00  0.00           H  
HETATM   26  H2  UNL     1      -0.151   0.726  -3.079  1.00  0.00           H  
HETATM   27  H3  UNL     1      -0.128  -1.115  -3.165  1.00  0.00           H  
HETATM   28  H4  UNL     1       1.339   0.295   1.552  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.314  -0.126  -1.666  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.740  -0.021  -1.690  1.00  0.00           H  
HETATM   31  H7  UNL     1       7.747   1.294   0.323  1.00  0.00           H  
HETATM   32  H8  UNL     1       5.749   0.639   2.463  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.695  -0.298   2.679  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.595   0.441   2.968  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.028   0.500   3.390  1.00  0.00           H  
HETATM   36  H12 UNL     1      -6.587   0.040   1.519  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.670  -0.471  -0.727  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   22
CONECT    3    4   14   14
CONECT    4    5    5    6
CONECT    6    7   28
CONECT    7    8    8   13
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   12
CONECT   11   31
CONECT   12   13   13   32
CONECT   14   15   16
CONECT   15   33
CONECT   16   17   17   21
CONECT   17   18   34
CONECT   18   19   19   35
CONECT   19   20   36
CONECT   20   21   21   37
CONECT   21   22
CONECT   22   23   23   24   24
END

HMDB0014096
     RDKit          3D
5'-Hydroxypiroxicam
 37 39  0  0  0  0  0  0  0  0999 V2000
   -0.7263   -0.2247   -2.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3509   -0.3473   -1.6795 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -0.1140   -0.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8118   -0.0569   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864   -0.2226   -1.6968 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6745    0.1525    0.5555 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0815    0.1945    0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8038    0.0458   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2101    0.1029   -0.7604 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8903    0.3173    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2942    0.3882    0.4459 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1616    0.4673    1.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    0.4086    1.5540 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3151    0.0310    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5805    0.2678    1.8459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7679   -0.0464    0.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3052    0.2397    2.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6472    0.2716    2.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5227    0.0165    1.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0059   -0.2666    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6589   -0.2976   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0175   -0.7621   -1.6756 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.7785   -0.0516   -2.7543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2081   -2.2661   -1.7843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5327   -0.1525   -3.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    0.7258   -3.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276   -1.1147   -3.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393    0.2954    1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3137   -0.1262   -1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7402   -0.0208   -1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7473    1.2936    0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7491    0.6390    2.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6950   -0.2983    2.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5945    0.4414    2.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0280    0.5002    3.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5869    0.0403    1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6703   -0.4711   -0.7265 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  3 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  2  0
 22  2  1  0
 13  7  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Hydroxypiroxicam	HMDB
4-Hydroxy-N-(5-hydroxypyridin-2-yl)-2-methyl-1,1-dioxo-2H-1λ⁶,2-benzothiazine-3-carboximidate	HMDB
5'-Hydroxypiroxicam	MeSH

Chemical Formula

C₁₅H₁₃N₃O₅S

Average Molecular Weight

347.346

Monoisotopic Molecular Weight

347.057591231

IUPAC Name

4-hydroxy-N-(5-hydroxypyridin-2-yl)-2-methyl-1,1-dioxo-2H-1λ⁶,2-benzothiazine-3-carboxamide

Traditional Name

4-hydroxy-N-(5-hydroxypyridin-2-yl)-2-methyl-1,1-dioxo-1λ⁶,2-benzothiazine-3-carboxamide

CAS Registry Number

77459-78-0

SMILES

CN1C(C(=O)NC2=NC=C(O)C=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O

InChI Identifier

InChI=1S/C15H13N3O5S/c1-18-13(15(21)17-12-7-6-9(19)8-16-12)14(20)10-4-2-3-5-11(10)24(18,22)23/h2-8,19-20H,1H3,(H,16,17,21)

InChI Key

CCKOORANQAQKKV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Not Available

Direct Parent

Benzothiazines

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Benzothiazine
N-arylamide
Hydroxypyridine
Ortho-thiazine
Pyridine
Organosulfonic acid amide
Benzenoid
Imidolactam
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Heteroaromatic compound
Vinylogous acid
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0014096)
Kidney (HMDB: HMDB0014096)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014096)

Source

Endogenous

Endogenous (HMDB: HMDB0014096)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	2.07	ALOGPS
logP	0.3	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.66	ChemAxon
pKa (Strongest Basic)	3.72	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.02 m³·mol⁻¹	ChemAxon
Polarizability	33.29 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]+	177.817	31661259
DarkChem	[M-H]-	179.248	31661259
DeepCCS	[M+H]+	175.126	30932474
DeepCCS	[M-H]-	172.768	30932474
DeepCCS	[M-2H]-	206.645	30932474
DeepCCS	[M+Na]+	181.872	30932474
AllCCS	[M+H]+	179.1	32859911
AllCCS	[M+H-H2O]+	176.0	32859911
AllCCS	[M+NH4]+	182.1	32859911
AllCCS	[M+Na]+	182.9	32859911
AllCCS	[M-H]-	175.2	32859911
AllCCS	[M+Na-2H]-	174.9	32859911
AllCCS	[M+HCOO]-	174.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.07 minutes	32390414
Predicted by Siyang on May 30, 2022	11.5017 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.63 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1621.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	251.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	104.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	88.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	410.7 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	553.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	861.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	294.1 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	1420.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	283.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	328.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	489.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	154.6 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	196.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5'-Hydroxypiroxicam	CN1C(C(=O)NC2=NC=C(O)C=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O	4933.5	Standard polar	33892256
5'-Hydroxypiroxicam	CN1C(C(=O)NC2=NC=C(O)C=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O	2554.9	Standard non polar	33892256
5'-Hydroxypiroxicam	CN1C(C(=O)NC2=NC=C(O)C=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O	3085.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5'-Hydroxypiroxicam,1TMS,isomer #1	CN1C(C(=O)NC2=CC=C(O[Si](C)(C)C)C=N2)=C(O)C2=CC=CC=C2S1(=O)=O	3151.6	Semi standard non polar	33892256
5'-Hydroxypiroxicam,1TMS,isomer #2	CN1C(C(=O)NC2=CC=C(O)C=N2)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O	3033.5	Semi standard non polar	33892256
5'-Hydroxypiroxicam,1TMS,isomer #3	CN1C(C(=O)N(C2=CC=C(O)C=N2)[Si](C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O	3049.3	Semi standard non polar	33892256
5'-Hydroxypiroxicam,2TMS,isomer #1	CN1C(C(=O)NC2=CC=C(O[Si](C)(C)C)C=N2)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O	3112.3	Semi standard non polar	33892256
5'-Hydroxypiroxicam,2TMS,isomer #2	CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C)C=N2)[Si](C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O	3002.2	Semi standard non polar	33892256
5'-Hydroxypiroxicam,2TMS,isomer #3	CN1C(C(=O)N(C2=CC=C(O)C=N2)[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O	2955.1	Semi standard non polar	33892256
5'-Hydroxypiroxicam,3TMS,isomer #1	CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C)C=N2)[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O	3031.4	Semi standard non polar	33892256
5'-Hydroxypiroxicam,3TMS,isomer #1	CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C)C=N2)[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O	3205.9	Standard non polar	33892256
5'-Hydroxypiroxicam,3TMS,isomer #1	CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C)C=N2)[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O	3858.2	Standard polar	33892256
5'-Hydroxypiroxicam,1TBDMS,isomer #1	CN1C(C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)=C(O)C2=CC=CC=C2S1(=O)=O	3380.5	Semi standard non polar	33892256
5'-Hydroxypiroxicam,1TBDMS,isomer #2	CN1C(C(=O)NC2=CC=C(O)C=N2)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O	3358.7	Semi standard non polar	33892256
5'-Hydroxypiroxicam,1TBDMS,isomer #3	CN1C(C(=O)N(C2=CC=C(O)C=N2)[Si](C)(C)C(C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O	3319.9	Semi standard non polar	33892256
5'-Hydroxypiroxicam,2TBDMS,isomer #1	CN1C(C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O	3552.2	Semi standard non polar	33892256
5'-Hydroxypiroxicam,2TBDMS,isomer #2	CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O	3488.4	Semi standard non polar	33892256
5'-Hydroxypiroxicam,2TBDMS,isomer #3	CN1C(C(=O)N(C2=CC=C(O)C=N2)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O	3449.6	Semi standard non polar	33892256
5'-Hydroxypiroxicam,3TBDMS,isomer #1	CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O	3662.1	Semi standard non polar	33892256
5'-Hydroxypiroxicam,3TBDMS,isomer #1	CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O	3870.1	Standard non polar	33892256
5'-Hydroxypiroxicam,3TBDMS,isomer #1	CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O	3994.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Hydroxypiroxicam GC-MS (Non-derivatized) - 70eV, Positive	splash10-066r-1901000000-bca0ad1100e7a763c2c5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Hydroxypiroxicam GC-MS (2 TMS) - 70eV, Positive	splash10-0096-4191300000-4017f7f23d19f4a7fbdb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Hydroxypiroxicam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 10V, Positive-QTOF	splash10-0a4j-0904000000-95690a397314ea77af1a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 20V, Positive-QTOF	splash10-0a4i-0900000000-d1dba4d53826b8e36d40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 40V, Positive-QTOF	splash10-0a4i-6900000000-eb238be5bf46c09fb649	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 10V, Negative-QTOF	splash10-0002-0319000000-6cc58783b95d25f3be4b	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 20V, Negative-QTOF	splash10-0a4j-0869000000-3741c3a0d125983f0fcb	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 40V, Negative-QTOF	splash10-0a4l-4900000000-ebc70de8e15626839d14	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 10V, Negative-QTOF	splash10-000t-0597000000-d2c3d3f5469942a8cc05	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 20V, Negative-QTOF	splash10-01wk-0930000000-f2b3b1a88c48458f8ced	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 40V, Negative-QTOF	splash10-114i-3960000000-4792415f0204acfbb327	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 10V, Positive-QTOF	splash10-0002-0009000000-c86c5a1acb4218514ecf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 20V, Positive-QTOF	splash10-06r2-0926000000-e264276586b75fd8887f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 40V, Positive-QTOF	splash10-0bti-3910000000-fa6a3854baf7225a37e2	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Piroxicam 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	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

20129664

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54676301

PDB ID

Not Available

ChEBI ID

320793

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

Blanco FJ, Guitian R, Moreno J, de Toro FJ, Galdo F: Effect of antiinflammatory drugs on COX-1 and COX-2 activity in human articular chondrocytes. J Rheumatol. 1999 Jun;26(6):1366-73. [PubMed:10381057 ]
Bugajski J, Glod R, Gadek-Michalska A, Bugajski AJ: Involvement of constitutive (COX-1) and inducible cyclooxygenase (COX-2) in the adrenergic-induced ACTH and corticosterone secretion. J Physiol Pharmacol. 2001 Dec;52(4 Pt 2):795-809. [PubMed:11785774 ]
Fackovcova D, Kristova V, Kriska M: Renal damage induced by the treatment with non-opioid analgesics--theoretical assumption or clinical significance. Bratisl Lek Listy. 2000;101(8):417-22. [PubMed:11153163 ]
Raju J, Bird RP: Differential modulation of transforming growth factor-betas and cyclooxygenases in the platelet lysates of male F344 rats by dietary lipids and piroxicam. Mol Cell Biochem. 2002 Feb;231(1-2):139-46. [PubMed:11952155 ]
Veiga AP, Duarte ID, Avila MN, da Motta PG, Tatsuo MA, Francischi JN: Prevention by celecoxib of secondary hyperalgesia induced by formalin in rats. Life Sci. 2004 Oct 22;75(23):2807-17. [PubMed:15464832 ]
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

Blanco FJ, Guitian R, Moreno J, de Toro FJ, Galdo F: Effect of antiinflammatory drugs on COX-1 and COX-2 activity in human articular chondrocytes. J Rheumatol. 1999 Jun;26(6):1366-73. [PubMed:10381057 ]
Bugajski J, Glod R, Gadek-Michalska A, Bugajski AJ: Involvement of constitutive (COX-1) and inducible cyclooxygenase (COX-2) in the adrenergic-induced ACTH and corticosterone secretion. J Physiol Pharmacol. 2001 Dec;52(4 Pt 2):795-809. [PubMed:11785774 ]
Fackovcova D, Kristova V, Kriska M: Renal damage induced by the treatment with non-opioid analgesics--theoretical assumption or clinical significance. Bratisl Lek Listy. 2000;101(8):417-22. [PubMed:11153163 ]
Raju J, Bird RP: Differential modulation of transforming growth factor-betas and cyclooxygenases in the platelet lysates of male F344 rats by dietary lipids and piroxicam. Mol Cell Biochem. 2002 Feb;231(1-2):139-46. [PubMed:11952155 ]
Veiga AP, Duarte ID, Avila MN, da Motta PG, Tatsuo MA, Francischi JN: Prevention by celecoxib of secondary hyperalgesia induced by formalin in rats. Life Sci. 2004 Oct 22;75(23):2807-17. [PubMed:15464832 ]

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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, Raunio H: Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica. 1998 Dec;28(12):1203-53. [PubMed:9890159 ]
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 2C8

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

References

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 ]

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

Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H: Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75. [PubMed:12063169 ]
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

Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [PubMed:10991954 ]
Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [PubMed:11669456 ]
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 ]
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 ]
Tsuda M, Sekine T, Takeda M, Cha SH, Kanai Y, Kimura M, Endou H: Transport of ochratoxin A by renal multispecific organic anion transporter 1. J Pharmacol Exp Ther. 1999 Jun;289(3):1301-5. [PubMed:10336520 ]

Showing metabocard for 5'-Hydroxypiroxicam (HMDB0014096)

MOL for HMDB0014096 (5'-Hydroxypiroxicam)

3D MOL for HMDB0014096 (5'-Hydroxypiroxicam)

3D SDF for HMDB0014096 (5'-Hydroxypiroxicam)

3D-SDF for HMDB0014096 (5'-Hydroxypiroxicam)

PDB for HMDB0014096 (5'-Hydroxypiroxicam)

3D PDB for HMDB0014096 (5'-Hydroxypiroxicam)

SMILES for HMDB0014096 (5'-Hydroxypiroxicam)

INCHI for HMDB0014096 (5'-Hydroxypiroxicam)

Structure for HMDB0014096 (5'-Hydroxypiroxicam)

3D Structure for HMDB0014096 (5'-Hydroxypiroxicam)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

Transporters

References

References