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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014612

Secondary Accession Numbers

HMDB14612

Metabolite Identification

Common Name

Tenoxicam

Description

Tenoxicam is only found in individuals that have used or taken this drug. It is an antiinflammatory agent with analgesic and antipyretic properties, and is used to treat osteoarthritis and control acute pain.The antiinflammatory effects of tenoxicam may result from the inhibition of the enzyme cycooxygenase and the subsequent peripheral inhibition of prostaglandin synthesis. As prostaglandins sensitize pain receptors, their inhibition accounts for the peripheral analgesic effects of tenoxicam. Antipyresis may occur by central action on the hypothalamus, resulting in peripheral dilation, increased cutaneous blood flow, and subsequent heat loss.

Structure

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

HMDB0014612
     RDKit          3D
Tenoxicam
 33 35  0  0  0  0  0  0  0  0999 V2000
    0.9042    2.7643   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056    1.4885   -0.6067 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5652    0.3454   -0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724    0.4015   -1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1643    1.5901   -1.6700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4963   -0.7548   -1.2416 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6168   -0.9384   -0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9595    0.0035    0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0279   -0.1636    1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8069   -1.3090    1.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4160   -2.2228    0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3576   -2.0497   -0.4837 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642   -0.9049   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2888   -1.9135   -0.2420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903   -1.1239    0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -2.5475    1.0618 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6339   -1.8822    1.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165   -0.5789    1.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3473   -0.1876    0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9742    1.4730    0.0299 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.1640    2.3646    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9359    1.8342   -1.0924 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    2.7640   -2.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0586    3.1621   -0.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999    3.5567   -0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6176    1.6968   -2.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638   -1.4932   -1.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3308    0.8945    0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3005    0.5845    2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6654   -1.4781    1.9164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0187   -3.1241    0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5087   -2.3633    1.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3780    0.1117    1.3292 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
 11 12  2  0
  3 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  2  0
 20  2  1  0
 12  7  1  0
 19 15  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 17 32  1  0
 18 33  1  0
M  END

469
  Mrv0541 02231214422D          

 22 24  0  0  1  0            999 V2000
    5.2224    1.7053    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176    0.2164    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350    2.4198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    2.4198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.7697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.2928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.7697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.0073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176    1.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1991    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.0073    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  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
M  END
> <DATABASE_ID>
HMDB0014612

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H11N3O4S2/c1-16-10(13(18)15-9-4-2-3-6-14-9)11(17)12-8(5-7-21-12)22(16,19)20/h2-7,18H,1H3,(H,14,15)/b13-10-

> <INCHI_KEY>
WZWYJBNHTWCXIM-RAXLEYEMSA-N

> <FORMULA>
C13H11N3O4S2

> <MOLECULAR_WEIGHT>
337.374

> <EXACT_MASS>
337.019097235

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.083696750080794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
1.2218269856666666

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.631263884789849

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.207648848151218

> <JCHEM_PKA_STRONGEST_BASIC>
4.781645705752465

> <JCHEM_POLAR_SURFACE_AREA>
99.6

> <JCHEM_REFRACTIVITY>
93.05910000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tenoxicam

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014612
     RDKit          3D
Tenoxicam
 33 35  0  0  0  0  0  0  0  0999 V2000
    0.9042    2.7643   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056    1.4885   -0.6067 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5652    0.3454   -0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724    0.4015   -1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1643    1.5901   -1.6700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4963   -0.7548   -1.2416 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6168   -0.9384   -0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9595    0.0035    0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0279   -0.1636    1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8069   -1.3090    1.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4160   -2.2228    0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3576   -2.0497   -0.4837 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642   -0.9049   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2888   -1.9135   -0.2420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903   -1.1239    0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -2.5475    1.0618 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6339   -1.8822    1.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165   -0.5789    1.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3473   -0.1876    0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9742    1.4730    0.0299 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.1640    2.3646    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9359    1.8342   -1.0924 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    2.7640   -2.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0586    3.1621   -0.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999    3.5567   -0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6176    1.6968   -2.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638   -1.4932   -1.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3308    0.8945    0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3005    0.5845    2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6654   -1.4781    1.9164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0187   -3.1241    0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5087   -2.3633    1.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3780    0.1117    1.3292 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
 11 12  2  0
  3 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  2  0
 20  2  1  0
 12  7  1  0
 19 15  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 17 32  1  0
 18 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 469                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       9.748   3.183   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      12.540   0.404   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      10.519   4.517   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.978   4.517   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.748  -1.437   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.748   0.873   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       8.415   2.413   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       7.081  -1.437   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       5.748  -3.747   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      11.082   2.413   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   0.873   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082   0.873   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748   0.103   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.540   2.883   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   3.183   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   0.103   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.438   1.643   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748  -2.207   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -1.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080  -2.207   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414  -4.517   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080  -3.747   0.000  0.00  0.00           C+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                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0014612
HETATM    1  C1  UNL     1       0.904   2.764  -1.114  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.406   1.488  -0.607  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.565   0.345  -0.672  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.672   0.402  -1.186  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.164   1.590  -1.670  1.00  0.00           O  
HETATM    6  N2  UNL     1      -1.496  -0.755  -1.242  1.00  0.00           N  
HETATM    7  C4  UNL     1      -2.617  -0.938  -0.386  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.959   0.004   0.546  1.00  0.00           C  
HETATM    9  C6  UNL     1      -4.028  -0.164   1.367  1.00  0.00           C  
HETATM   10  C7  UNL     1      -4.807  -1.309   1.280  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.416  -2.223   0.325  1.00  0.00           C  
HETATM   12  N3  UNL     1      -3.358  -2.050  -0.484  1.00  0.00           N  
HETATM   13  C9  UNL     1       1.064  -0.905  -0.171  1.00  0.00           C  
HETATM   14  O2  UNL     1       0.289  -1.914  -0.242  1.00  0.00           O  
HETATM   15  C10 UNL     1       2.390  -1.124   0.418  1.00  0.00           C  
HETATM   16  S1  UNL     1       3.137  -2.547   1.062  1.00  0.00           S  
HETATM   17  C11 UNL     1       4.634  -1.882   1.507  1.00  0.00           C  
HETATM   18  C12 UNL     1       4.517  -0.579   1.147  1.00  0.00           C  
HETATM   19  C13 UNL     1       3.347  -0.188   0.580  1.00  0.00           C  
HETATM   20  S2  UNL     1       2.974   1.473   0.030  1.00  0.00           S  
HETATM   21  O3  UNL     1       3.164   2.365   1.211  1.00  0.00           O  
HETATM   22  O4  UNL     1       3.936   1.834  -1.092  1.00  0.00           O  
HETATM   23  H1  UNL     1       0.742   2.764  -2.206  1.00  0.00           H  
HETATM   24  H2  UNL     1       0.059   3.162  -0.517  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.700   3.557  -0.972  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.618   1.697  -2.575  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.264  -1.493  -1.940  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.331   0.895   0.594  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.300   0.585   2.107  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.665  -1.478   1.916  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.019  -3.124   0.247  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.509  -2.363   1.976  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.378   0.112   1.329  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   20
CONECT    3    4    4   13
CONECT    4    5    6
CONECT    5   26
CONECT    6    7   27
CONECT    7    8    8   12
CONECT    8    9   28
CONECT    9   10   10   29
CONECT   10   11   30
CONECT   11   12   12   31
CONECT   13   14   14   15
CONECT   15   16   19   19
CONECT   16   17
CONECT   17   18   18   32
CONECT   18   19   33
CONECT   19   20
CONECT   20   21   21   22   22
END

HMDB0014612
     RDKit          3D
Tenoxicam
 33 35  0  0  0  0  0  0  0  0999 V2000
    0.9042    2.7643   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056    1.4885   -0.6067 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5652    0.3454   -0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724    0.4015   -1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1643    1.5901   -1.6700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4963   -0.7548   -1.2416 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6168   -0.9384   -0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9595    0.0035    0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0279   -0.1636    1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8069   -1.3090    1.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4160   -2.2228    0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3576   -2.0497   -0.4837 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642   -0.9049   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2888   -1.9135   -0.2420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903   -1.1239    0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -2.5475    1.0618 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6339   -1.8822    1.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165   -0.5789    1.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3473   -0.1876    0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9742    1.4730    0.0299 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.1640    2.3646    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9359    1.8342   -1.0924 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    2.7640   -2.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0586    3.1621   -0.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999    3.5567   -0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6176    1.6968   -2.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638   -1.4932   -1.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3308    0.8945    0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3005    0.5845    2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6654   -1.4781    1.9164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0187   -3.1241    0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5087   -2.3633    1.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3780    0.1117    1.3292 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
 11 12  2  0
  3 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  2  0
 20  2  1  0
 12  7  1  0
 19 15  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 17 32  1  0
 18 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₁N₃O₄S₂

Average Molecular Weight

337.374

Monoisotopic Molecular Weight

337.019097235

IUPAC Name

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

Traditional Name

tenoxicam

CAS Registry Number

59804-37-4

SMILES

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

InChI Identifier

InChI=1S/C13H11N3O4S2/c1-16-10(13(18)15-9-4-2-3-6-14-9)11(17)12-8(5-7-21-12)22(16,19)20/h2-7,18H,1H3,(H,14,15)/b13-10-

InChI Key

WZWYJBNHTWCXIM-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
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

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	211 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.28 g/L	Not Available
LogP	1.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	170.4	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	1.82	ALOGPS
logP	1.22	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.21	ChemAxon
pKa (Strongest Basic)	4.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.06 m³·mol⁻¹	ChemAxon
Polarizability	31.08 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]+	170.031	30932474
DeepCCS	[M-H]-	167.673	30932474
DeepCCS	[M-2H]-	200.559	30932474
DeepCCS	[M+Na]+	176.125	30932474
AllCCS	[M+H]+	174.6	32859911
AllCCS	[M+H-H2O]+	171.3	32859911
AllCCS	[M+NH4]+	177.6	32859911
AllCCS	[M+Na]+	178.5	32859911
AllCCS	[M-H]-	170.6	32859911
AllCCS	[M+Na-2H]-	170.2	32859911
AllCCS	[M+HCOO]-	170.0	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.	4.77 minutes	32390414
Predicted by Siyang on May 30, 2022	13.7955 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.89 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	30.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2401.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	337.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	109.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	196.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	110.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	467.3 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	746.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	246.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1031.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	350.1 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	1686.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	371.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	360.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	660.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	253.1 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	220.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tenoxicam	CN1\C(=C(/O)NC2=CC=CC=N2)C(=O)C2=C(C=CS2)S1(=O)=O	4346.3	Standard polar	33892256
Tenoxicam	CN1\C(=C(/O)NC2=CC=CC=N2)C(=O)C2=C(C=CS2)S1(=O)=O	3051.6	Standard non polar	33892256
Tenoxicam	CN1\C(=C(/O)NC2=CC=CC=N2)C(=O)C2=C(C=CS2)S1(=O)=O	3110.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tenoxicam,1TMS,isomer #1	CN1/C(=C(/NC2=CC=CC=N2)O[Si](C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	2960.4	Semi standard non polar	33892256
Tenoxicam,1TMS,isomer #2	CN1/C(=C(\O)N(C2=CC=CC=N2)[Si](C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	2894.8	Semi standard non polar	33892256
Tenoxicam,2TMS,isomer #1	CN1/C(=C(\O[Si](C)(C)C)N(C2=CC=CC=N2)[Si](C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	2847.2	Semi standard non polar	33892256
Tenoxicam,2TMS,isomer #1	CN1/C(=C(\O[Si](C)(C)C)N(C2=CC=CC=N2)[Si](C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3054.0	Standard non polar	33892256
Tenoxicam,2TMS,isomer #1	CN1/C(=C(\O[Si](C)(C)C)N(C2=CC=CC=N2)[Si](C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3970.3	Standard polar	33892256
Tenoxicam,1TBDMS,isomer #1	CN1/C(=C(/NC2=CC=CC=N2)O[Si](C)(C)C(C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3166.8	Semi standard non polar	33892256
Tenoxicam,1TBDMS,isomer #2	CN1/C(=C(\O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3128.0	Semi standard non polar	33892256
Tenoxicam,2TBDMS,isomer #1	CN1/C(=C(\O[Si](C)(C)C(C)(C)C)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3202.1	Semi standard non polar	33892256
Tenoxicam,2TBDMS,isomer #1	CN1/C(=C(\O[Si](C)(C)C(C)(C)C)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3531.5	Standard non polar	33892256
Tenoxicam,2TBDMS,isomer #1	CN1/C(=C(\O[Si](C)(C)C(C)(C)C)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)C(=O)C2=C(C=CS2)S1(=O)=O	3988.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tenoxicam GC-MS (Non-derivatized) - 70eV, Positive	splash10-06xx-6921000000-0fa9ed6eb27f65ab5e87	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tenoxicam GC-MS (1 TMS) - 70eV, Positive	splash10-05gm-9684000000-6ff0dc448004badd8a55	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tenoxicam 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 - Tenoxicam 10V, Positive-QTOF	splash10-000j-6039000000-53a14285a4e96616e737	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenoxicam 20V, Positive-QTOF	splash10-0002-9200000000-866f760f37d21d133f09	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenoxicam 40V, Positive-QTOF	splash10-01ot-9800000000-da8feda830529845a342	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenoxicam 10V, Negative-QTOF	splash10-000i-4049000000-1c4fb3e51611360de787	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenoxicam 20V, Negative-QTOF	splash10-0006-8900000000-559e35dd6fe4470b2b78	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenoxicam 40V, Negative-QTOF	splash10-0595-9700000000-844763cbb5a5cf19a5cb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenoxicam 10V, Negative-QTOF	splash10-0uki-0987000000-e8f95a0ba78a644434cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenoxicam 20V, Negative-QTOF	splash10-014i-1290000000-5e6bfa711bfc215c7e8c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenoxicam 40V, Negative-QTOF	splash10-0006-9321000000-c457ce51bf0921b2c86b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenoxicam 10V, Positive-QTOF	splash10-000i-1009000000-e19553c6a13a8c1dfec0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenoxicam 20V, Positive-QTOF	splash10-000j-9438000000-7f26e4f41f53d5198c81	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tenoxicam 40V, Positive-QTOF	splash10-004i-9001000000-d4283aab6299b788dceb	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tenoxicam 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 DB00469	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00469	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

4471584

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tenoxicam

METLIN ID

Not Available

PubChem Compound

5312154

PDB ID

Not Available

ChEBI ID

553047

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 Tenoxicam (HMDB0014612)

MOL for HMDB0014612 (Tenoxicam)

3D MOL for HMDB0014612 (Tenoxicam)

3D SDF for HMDB0014612 (Tenoxicam)

3D-SDF for HMDB0014612 (Tenoxicam)

PDB for HMDB0014612 (Tenoxicam)

3D PDB for HMDB0014612 (Tenoxicam)

SMILES for HMDB0014612 (Tenoxicam)

INCHI for HMDB0014612 (Tenoxicam)

Structure for HMDB0014612 (Tenoxicam)

3D Structure for HMDB0014612 (Tenoxicam)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra