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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

HMDB0014098

Secondary Accession Numbers

HMDB14098

Metabolite Identification

Common Name

5'-Hydroxytenoxicam

Description

5'-Hydroxytenoxicam belongs to the class of organic compounds known as thienothiazines. These are heterocyclic compounds containing a thiophene ring fused to a thiazine. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Thiazine is a 6-membered ring consisting of four carbon, one nitrogen and one sulfur atoms. 5'-Hydroxytenoxicam is a metabolite of Tenoxicam. 5'-Hydroxytenoxicam is only found in individuals that have used or taken Tenoxicam. 5'-Hydroxytenoxicam is a strong basic compound (based on its pKa). These are heterocyclic compounds containing a thiophene ring fused to a thiazine.

Structure

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

HMDB0014098
     RDKit          3D
5'-Hydroxytenoxicam
 34 36  0  0  0  0  0  0  0  0999 V2000
    0.9634   -3.0554   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4994   -1.6881   -0.3956 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6732   -0.5997   -0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5677   -0.8626   -1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0586   -2.1418   -1.3094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    0.2262   -1.5208 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4081    0.6478   -0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5585    0.0318    0.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5075    0.4148    1.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3501    1.4721    1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3015    1.8738    2.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1705    2.0643   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2361    1.6678   -0.8903 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0829    0.7740   -0.6340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2914    1.7049   -0.9485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4235    1.1878   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1521    2.7248    0.0805 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6693    2.2158    0.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5717    0.8576    0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971    0.3218    0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -1.4292    0.0800 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.4669   -2.1085    1.3695 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0069   -1.9879   -1.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090   -3.7119   -0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528   -3.2332    0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8165   -3.4095   -1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7100   -2.3391   -2.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3136    0.6858   -2.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9161   -0.8099    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6136   -0.0705    2.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301    2.5920    2.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8384    2.8945   -0.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5449    2.8199    0.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4666    0.2699    0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  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  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  2  0
 21  2  1  0
 13  7  1  0
 20 16  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 18 33  1  0
 19 34  1  0
M  END


  Mrv0541 06191310522D          

 23 25  0  0  0  0            999 V2000
    9.8726   -2.1172    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.3678   -3.6061    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.2852   -1.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4601   -1.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8726   -4.5922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7293   -3.3547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1582   -2.5297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4437   -4.5922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7293   -5.8298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5872   -2.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1582   -3.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5872   -3.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8726   -3.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3678   -2.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4437   -2.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4437   -3.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8493   -2.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7293   -5.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0147   -4.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002   -5.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0147   -6.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002   -5.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5857   -6.2423    0.0000 O   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  7  1  0  0  0  0
  1 10  1  0  0  0  0
  2 12  1  0  0  0  0
  2 17  1  0  0  0  0
  5 13  2  0  0  0  0
  6 16  1  0  0  0  0
  7 11  1  0  0  0  0
  7 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 18  1  0  0  0  0
  9 18  1  0  0  0  0
  9 21  2  0  0  0  0
 10 12  2  0  0  0  0
 10 14  1  0  0  0  0
 11 13  1  0  0  0  0
 11 16  2  0  0  0  0
 12 13  1  0  0  0  0
 14 17  2  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014098

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1\C(=C(/O)NC2=CC=C(O)C=N2)C(=O)C2=C(C=CS2)S1(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H11N3O5S2/c1-16-10(13(19)15-9-3-2-7(17)6-14-9)11(18)12-8(4-5-22-12)23(16,20)21/h2-6,17,19H,1H3,(H,14,15)/b13-10-

> <INCHI_KEY>
INPPRTDYEGRTIU-RAXLEYEMSA-N

> <FORMULA>
C13H11N3O5S2

> <MOLECULAR_WEIGHT>
353.374

> <EXACT_MASS>
353.014011857

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
31.925840643002434

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z)-3-{hydroxy[(5-hydroxypyridin-2-yl)amino]methylidene}-2-methyl-2H,3H,4H-1λ⁶-thieno[2,3-e][1,2]thiazine-1,1,4-trione

> <ALOGPS_LOGP>
1.32

> <JCHEM_LOGP>
0.918261664

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.094716342362403

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.106505789045374

> <JCHEM_PKA_STRONGEST_BASIC>
4.745380676474475

> <JCHEM_POLAR_SURFACE_AREA>
119.83

> <JCHEM_REFRACTIVITY>
95.04

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-3-{hydroxy[(5-hydroxypyridin-2-yl)amino]methylidene}-2-methyl-1λ⁶-thieno[2,3-e][1,2]thiazine-1,1,4-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014098
     RDKit          3D
5'-Hydroxytenoxicam
 34 36  0  0  0  0  0  0  0  0999 V2000
    0.9634   -3.0554   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4994   -1.6881   -0.3956 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6732   -0.5997   -0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5677   -0.8626   -1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0586   -2.1418   -1.3094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    0.2262   -1.5208 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4081    0.6478   -0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5585    0.0318    0.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5075    0.4148    1.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3501    1.4721    1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3015    1.8738    2.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1705    2.0643   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2361    1.6678   -0.8903 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0829    0.7740   -0.6340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2914    1.7049   -0.9485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4235    1.1878   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1521    2.7248    0.0805 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6693    2.2158    0.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5717    0.8576    0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971    0.3218    0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -1.4292    0.0800 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.4669   -2.1085    1.3695 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0069   -1.9879   -1.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090   -3.7119   -0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528   -3.2332    0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8165   -3.4095   -1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7100   -2.3391   -2.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3136    0.6858   -2.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9161   -0.8099    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6136   -0.0705    2.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301    2.5920    2.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8384    2.8945   -0.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5449    2.8199    0.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4666    0.2699    0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  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  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  2  0
 21  2  1  0
 13  7  1  0
 20 16  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 18 33  1  0
 19 34  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  S   UNK     0      18.429  -3.952   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      21.220  -6.731   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      19.199  -2.618   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      17.659  -2.618   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      18.429  -8.572   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      14.428  -6.262   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      17.095  -4.722   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      15.762  -8.572   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      14.428 -10.882   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      19.763  -4.722   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.095  -6.262   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.763  -6.262   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.429  -7.032   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.220  -4.253   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.762  -3.952   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.762  -7.032   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.119  -5.492   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.428  -9.342   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.094  -8.572   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.760  -9.342   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.094 -11.652   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.760 -10.882   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.427 -11.652   0.000  0.00  0.00           O+0
CONECT    1    3    4    7   10                                             
CONECT    2   12   17                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5   13                                                            
CONECT    6   16                                                            
CONECT    7    1   11   15                                                  
CONECT    8   16   18                                                       
CONECT    9   18   21                                                       
CONECT   10    1   12   14                                                  
CONECT   11    7   13   16                                                  
CONECT   12    2   10   13                                                  
CONECT   13    5   11   12                                                  
CONECT   14   10   17                                                       
CONECT   15    7                                                            
CONECT   16    6    8   11                                                  
CONECT   17    2   14                                                       
CONECT   18    8    9   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   22                                                       
CONECT   21    9   22                                                       
CONECT   22   20   21   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0014098
HETATM    1  C1  UNL     1       0.963  -3.055  -0.446  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.499  -1.688  -0.396  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.673  -0.600  -0.732  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.568  -0.863  -1.173  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.059  -2.142  -1.309  1.00  0.00           O  
HETATM    6  N2  UNL     1      -1.426   0.226  -1.521  1.00  0.00           N  
HETATM    7  C4  UNL     1      -2.408   0.648  -0.604  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.558   0.032   0.622  1.00  0.00           C  
HETATM    9  C6  UNL     1      -3.508   0.415   1.547  1.00  0.00           C  
HETATM   10  C7  UNL     1      -4.350   1.472   1.224  1.00  0.00           C  
HETATM   11  O2  UNL     1      -5.302   1.874   2.124  1.00  0.00           O  
HETATM   12  C8  UNL     1      -4.170   2.064  -0.010  1.00  0.00           C  
HETATM   13  N3  UNL     1      -3.236   1.668  -0.890  1.00  0.00           N  
HETATM   14  C9  UNL     1       1.083   0.774  -0.634  1.00  0.00           C  
HETATM   15  O3  UNL     1       0.291   1.705  -0.948  1.00  0.00           O  
HETATM   16  C10 UNL     1       2.423   1.188  -0.171  1.00  0.00           C  
HETATM   17  S1  UNL     1       3.152   2.725   0.080  1.00  0.00           S  
HETATM   18  C11 UNL     1       4.669   2.216   0.652  1.00  0.00           C  
HETATM   19  C12 UNL     1       4.572   0.858   0.632  1.00  0.00           C  
HETATM   20  C13 UNL     1       3.397   0.322   0.201  1.00  0.00           C  
HETATM   21  S2  UNL     1       3.118  -1.429   0.080  1.00  0.00           S  
HETATM   22  O4  UNL     1       3.467  -2.109   1.369  1.00  0.00           O  
HETATM   23  O5  UNL     1       4.007  -1.988  -1.016  1.00  0.00           O  
HETATM   24  H1  UNL     1       1.809  -3.712  -0.061  1.00  0.00           H  
HETATM   25  H2  UNL     1       0.153  -3.233   0.263  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.816  -3.409  -1.475  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.710  -2.339  -2.042  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.314   0.686  -2.435  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.916  -0.810   0.925  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.614  -0.070   2.492  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.130   2.592   2.839  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.838   2.894  -0.253  1.00  0.00           H  
HETATM   33  H10 UNL     1       5.545   2.820   0.971  1.00  0.00           H  
HETATM   34  H11 UNL     1       5.467   0.270   0.973  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   21
CONECT    3    4    4   14
CONECT    4    5    6
CONECT    5   27
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   15   16
CONECT   16   17   20   20
CONECT   17   18
CONECT   18   19   19   33
CONECT   19   20   34
CONECT   20   21
CONECT   21   22   22   23   23
END

HMDB0014098
     RDKit          3D
5'-Hydroxytenoxicam
 34 36  0  0  0  0  0  0  0  0999 V2000
    0.9634   -3.0554   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4994   -1.6881   -0.3956 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6732   -0.5997   -0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5677   -0.8626   -1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0586   -2.1418   -1.3094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    0.2262   -1.5208 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4081    0.6478   -0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5585    0.0318    0.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5075    0.4148    1.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3501    1.4721    1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3015    1.8738    2.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1705    2.0643   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2361    1.6678   -0.8903 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0829    0.7740   -0.6340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2914    1.7049   -0.9485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4235    1.1878   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1521    2.7248    0.0805 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6693    2.2158    0.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5717    0.8576    0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971    0.3218    0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -1.4292    0.0800 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.4669   -2.1085    1.3695 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0069   -1.9879   -1.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090   -3.7119   -0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528   -3.2332    0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8165   -3.4095   -1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7100   -2.3391   -2.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3136    0.6858   -2.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9161   -0.8099    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6136   -0.0705    2.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301    2.5920    2.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8384    2.8945   -0.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5449    2.8199    0.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4666    0.2699    0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  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  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  2  0
 21  2  1  0
 13  7  1  0
 20 16  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 18 33  1  0
 19 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₁N₃O₅S₂

Average Molecular Weight

353.374

Monoisotopic Molecular Weight

353.014011857

IUPAC Name

(3Z)-3-{hydroxy[(5-hydroxypyridin-2-yl)amino]methylidene}-2-methyl-2H,3H,4H-1λ⁶-thieno[2,3-e][1,2]thiazine-1,1,4-trione

Traditional Name

(3Z)-3-{hydroxy[(5-hydroxypyridin-2-yl)amino]methylidene}-2-methyl-1λ⁶-thieno[2,3-e][1,2]thiazine-1,1,4-trione

CAS Registry Number

Not Available

SMILES

CN1\C(=C(/O)NC2=CC=C(O)C=N2)C(=O)C2=C(C=CS2)S1(=O)=O

InChI Identifier

InChI=1S/C13H11N3O5S2/c1-16-10(13(19)15-9-3-2-7(17)6-14-9)11(18)12-8(4-5-22-12)23(16,20)21/h2-6,17,19H,1H3,(H,14,15)/b13-10-

InChI Key

INPPRTDYEGRTIU-RAXLEYEMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thienothiazines. These are heterocyclic compounds containing a thiophene ring fused to a thiazine. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Thiazine is a 6-membered ring consisting of four carbon, one nitrogen and one sulfur atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thienothiazines

Sub Class

Not Available

Direct Parent

Thienothiazines

Alternative Parents

Substituents

Thienothiazine
Aryl ketone
Secondary aliphatic/aromatic amine
Hydroxypyridine
Ortho-thiazine
Pyridine
Imidolactam
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Heteroaromatic compound
Organosulfonic acid or derivatives
Vinylogous amide
Vinylogous acid
Thiophene
Ketone
Alkanolamine
Secondary amine
Azacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Liver (HMDB: HMDB0014098)
Kidney (HMDB: HMDB0014098)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014098)

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	0.42 g/L	ALOGPS
logP	1.32	ALOGPS
logP	0.92	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.11	ChemAxon
pKa (Strongest Basic)	4.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.04 m³·mol⁻¹	ChemAxon
Polarizability	31.93 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	175.954	30932474
DeepCCS	[M-H]-	173.596	30932474
DeepCCS	[M-2H]-	207.091	30932474
DeepCCS	[M+Na]+	182.318	30932474
AllCCS	[M+H]+	177.6	32859911
AllCCS	[M+H-H2O]+	174.5	32859911
AllCCS	[M+NH4]+	180.5	32859911
AllCCS	[M+Na]+	181.3	32859911
AllCCS	[M-H]-	173.1	32859911
AllCCS	[M+Na-2H]-	172.7	32859911
AllCCS	[M+HCOO]-	172.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5'-Hydroxytenoxicam	CN1\C(=C(/O)NC2=CC=C(O)C=N2)C(=O)C2=C(C=CS2)S1(=O)=O	4701.5	Standard polar	33892256
5'-Hydroxytenoxicam	CN1\C(=C(/O)NC2=CC=C(O)C=N2)C(=O)C2=C(C=CS2)S1(=O)=O	3217.7	Standard non polar	33892256
5'-Hydroxytenoxicam	CN1\C(=C(/O)NC2=CC=C(O)C=N2)C(=O)C2=C(C=CS2)S1(=O)=O	3410.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5'-Hydroxytenoxicam,1TMS,isomer #1	CN1/C(=C(/NC2=CC=C(O)C=N2)O[Si](C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3184.7	Semi standard non polar	33892256
5'-Hydroxytenoxicam,1TMS,isomer #2	CN1/C(=C(\O)NC2=CC=C(O[Si](C)(C)C)C=N2)C(=O)C2=C(C=CS2)S1(=O)=O	3191.8	Semi standard non polar	33892256
5'-Hydroxytenoxicam,1TMS,isomer #3	CN1/C(=C(\O)N(C2=CC=C(O)C=N2)[Si](C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3114.2	Semi standard non polar	33892256
5'-Hydroxytenoxicam,2TMS,isomer #1	CN1/C(=C(/NC2=CC=C(O[Si](C)(C)C)C=N2)O[Si](C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3230.1	Semi standard non polar	33892256
5'-Hydroxytenoxicam,2TMS,isomer #2	CN1/C(=C(\O[Si](C)(C)C)N(C2=CC=C(O)C=N2)[Si](C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3036.2	Semi standard non polar	33892256
5'-Hydroxytenoxicam,2TMS,isomer #3	CN1/C(=C(\O)N(C2=CC=C(O[Si](C)(C)C)C=N2)[Si](C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3138.6	Semi standard non polar	33892256
5'-Hydroxytenoxicam,3TMS,isomer #1	CN1/C(=C(\O[Si](C)(C)C)N(C2=CC=C(O[Si](C)(C)C)C=N2)[Si](C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3128.9	Semi standard non polar	33892256
5'-Hydroxytenoxicam,3TMS,isomer #1	CN1/C(=C(\O[Si](C)(C)C)N(C2=CC=C(O[Si](C)(C)C)C=N2)[Si](C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3351.2	Standard non polar	33892256
5'-Hydroxytenoxicam,3TMS,isomer #1	CN1/C(=C(\O[Si](C)(C)C)N(C2=CC=C(O[Si](C)(C)C)C=N2)[Si](C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	4004.7	Standard polar	33892256
5'-Hydroxytenoxicam,1TBDMS,isomer #1	CN1/C(=C(/NC2=CC=C(O)C=N2)O[Si](C)(C)C(C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3420.5	Semi standard non polar	33892256
5'-Hydroxytenoxicam,1TBDMS,isomer #2	CN1/C(=C(\O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)C(=O)C2=C(C=CS2)S1(=O)=O	3421.7	Semi standard non polar	33892256
5'-Hydroxytenoxicam,1TBDMS,isomer #3	CN1/C(=C(\O)N(C2=CC=C(O)C=N2)[Si](C)(C)C(C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3383.7	Semi standard non polar	33892256
5'-Hydroxytenoxicam,2TBDMS,isomer #1	CN1/C(=C(/NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)O[Si](C)(C)C(C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3651.8	Semi standard non polar	33892256
5'-Hydroxytenoxicam,2TBDMS,isomer #2	CN1/C(=C(\O[Si](C)(C)C(C)(C)C)N(C2=CC=C(O)C=N2)[Si](C)(C)C(C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3445.6	Semi standard non polar	33892256
5'-Hydroxytenoxicam,2TBDMS,isomer #3	CN1/C(=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=C(C=CS2)S1(=O)=O	3624.7	Semi standard non polar	33892256
5'-Hydroxytenoxicam,3TBDMS,isomer #1	CN1/C(=C(\O[Si](C)(C)C(C)(C)C)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3723.5	Semi standard non polar	33892256
5'-Hydroxytenoxicam,3TBDMS,isomer #1	CN1/C(=C(\O[Si](C)(C)C(C)(C)C)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	4025.4	Standard non polar	33892256
5'-Hydroxytenoxicam,3TBDMS,isomer #1	CN1/C(=C(\O[Si](C)(C)C(C)(C)C)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	4097.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Hydroxytenoxicam GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2931000000-8a124e621bd74aa5d477	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Hydroxytenoxicam GC-MS (2 TMS) - 70eV, Positive	splash10-0abi-3629300000-fa2c519001a5160e74e1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Hydroxytenoxicam 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'-Hydroxytenoxicam 10V, Positive-QTOF	splash10-0w29-0629000000-cba3761c172aee44d636	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxytenoxicam 20V, Positive-QTOF	splash10-03di-2900000000-615be0cd38e52a99673b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxytenoxicam 40V, Positive-QTOF	splash10-01ri-6910000000-85f0c2e34e99e12adc2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxytenoxicam 10V, Negative-QTOF	splash10-0uxr-0359000000-eafe38336b094b8117e7	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxytenoxicam 20V, Negative-QTOF	splash10-0udi-2591000000-5a03b2dff0c457dc4ffe	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxytenoxicam 40V, Negative-QTOF	splash10-0592-6900000000-c9c734799e5e90d7f0f6	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxytenoxicam 10V, Positive-QTOF	splash10-0udi-0209000000-c78666639aad3edc6b12	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxytenoxicam 20V, Positive-QTOF	splash10-0pvi-1923000000-5ad9d4db111003f0f71a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxytenoxicam 40V, Positive-QTOF	splash10-06sr-7921000000-b6e0c33e6d8bc42e8724	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxytenoxicam 10V, Negative-QTOF	splash10-0udr-0595000000-28ec55ebb2f50bd0ed2e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxytenoxicam 20V, Negative-QTOF	splash10-014i-0490000000-b0e6474150f8a30dee57	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Hydroxytenoxicam 40V, Negative-QTOF	splash10-0bt9-9850000000-d8788144777ef3476100	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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

Showing metabocard for 5'-Hydroxytenoxicam (HMDB0014098)

MOL for HMDB0014098 (5'-Hydroxytenoxicam)

3D MOL for HMDB0014098 (5'-Hydroxytenoxicam)

3D SDF for HMDB0014098 (5'-Hydroxytenoxicam)

3D-SDF for HMDB0014098 (5'-Hydroxytenoxicam)

PDB for HMDB0014098 (5'-Hydroxytenoxicam)

3D PDB for HMDB0014098 (5'-Hydroxytenoxicam)

SMILES for HMDB0014098 (5'-Hydroxytenoxicam)

INCHI for HMDB0014098 (5'-Hydroxytenoxicam)

Structure for HMDB0014098 (5'-Hydroxytenoxicam)

3D Structure for HMDB0014098 (5'-Hydroxytenoxicam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra