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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:58:53 UTC

Update Date

2019-07-23 07:15:04 UTC

HMDB ID

HMDB0060779

Secondary Accession Numbers

HMDB60779

Metabolite Identification

Common Name

5'-Carboxy meloxicam

Description

5'-Carboxy meloxicam 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). It is a derivative of oxicam, closely related to piroxicam, and falls in the enolic acid group of NSAIDs. 5'-Carboxy meloxicam is an extremely weak basic (essentially neutral) compound (based on its pKa). 5'-Carboxy meloxicam is a metabolite of meloxicam. It was developed by Boehringer-Ingelheim. Meloxicam is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and fever reducer effects.

Structure

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

HMDB0060779
     RDKit          3D
5'-Carboxy meloxicam
 36 38  0  0  0  0  0  0  0  0999 V2000
   -1.2289   -2.7994   -0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6992   -1.4931   -0.3934 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120   -0.4511   -0.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6274   -0.7356   -0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1395   -1.9931   -0.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878    0.1761    0.2621 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9051   -0.0810    0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5340   -1.1846    0.6688 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8238   -1.2399    0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4955   -0.1307    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9495    0.0506    0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7518   -0.8594    0.3365 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3901    1.2679   -0.4410 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2071    0.9377   -0.1585 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840    0.7798    0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1948    1.7353    0.5659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5507    1.2262    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291    2.5617    0.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0983    3.0735    0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1753    2.2587    0.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9072    0.9294    0.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466    0.4535   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980   -1.2113   -0.4308 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.9984   -2.0591    0.6752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9938   -1.5564   -1.7600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5939   -2.8369   -1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0724   -3.5069   -0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130   -3.3173    0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903   -2.1281   -1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3920   -2.1439    0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6288    2.0414    0.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0936    1.9160    1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0234    3.2560    0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2677    4.1088    0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1611    2.6644    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7685    0.2910   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
  3 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  2  0
 23  2  1  0
 14  7  1  0
 22 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  9 30  1  0
 13 31  1  0
 16 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
M  END


  Mrv0541 07041311582D          

 25 27  0  0  0  0            999 V2000
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8781    1.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4656    2.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8011    2.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3260    0.9019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3162    3.6506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6216    3.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6586    2.0580    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  2  0  0  0  0
  9  5  2  0  0  0  0
  9  7  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  8  1  0  0  0  0
 15  6  1  0  0  0  0
 15 14  2  0  0  0  0
 16 12  2  0  0  0  0
 16 14  1  4  0  0  0
 17  1  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  2  0  0  0  0
 21 13  1  0  0  0  0
 24  8  1  0  0  0  0
 24 14  1  0  0  0  0
 25  9  1  0  0  0  0
 25 17  1  0  0  0  0
 25 22  2  0  0  0  0
 25 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060779

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(C(O)=NC2=NC=C(S2)C(O)=O)=C(O)C2=CC=CC=C2S1(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H11N3O6S2/c1-17-10(12(19)16-14-15-6-8(24-14)13(20)21)11(18)7-4-2-3-5-9(7)25(17,22)23/h2-6,18H,1H3,(H,20,21)(H,15,16,19)

> <INCHI_KEY>
MTQQFYLGAZXHTB-UHFFFAOYSA-N

> <FORMULA>
C14H11N3O6S2

> <MOLECULAR_WEIGHT>
381.384

> <EXACT_MASS>
381.008926479

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
35.587360156820665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[hydroxy(4-hydroxy-2-methyl-1,1-dioxo-2H-1λ⁶,2-benzothiazin-3-yl)methylidene]amino}-1,3-thiazole-5-carboxylic acid

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
1.472199549666667

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.83268578567014

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.833729960667056

> <JCHEM_PKA_STRONGEST_BASIC>
-0.12426238528283606

> <JCHEM_POLAR_SURFACE_AREA>
140.39000000000001

> <JCHEM_REFRACTIVITY>
91.36399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[hydroxy(4-hydroxy-2-methyl-1,1-dioxo-1λ⁶,2-benzothiazin-3-yl)methylidene]amino}-1,3-thiazole-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060779
     RDKit          3D
5'-Carboxy meloxicam
 36 38  0  0  0  0  0  0  0  0999 V2000
   -1.2289   -2.7994   -0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6992   -1.4931   -0.3934 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120   -0.4511   -0.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6274   -0.7356   -0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1395   -1.9931   -0.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878    0.1761    0.2621 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9051   -0.0810    0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5340   -1.1846    0.6688 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8238   -1.2399    0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4955   -0.1307    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9495    0.0506    0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7518   -0.8594    0.3365 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3901    1.2679   -0.4410 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2071    0.9377   -0.1585 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840    0.7798    0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1948    1.7353    0.5659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5507    1.2262    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291    2.5617    0.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0983    3.0735    0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1753    2.2587    0.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9072    0.9294    0.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466    0.4535   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980   -1.2113   -0.4308 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.9984   -2.0591    0.6752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9938   -1.5564   -1.7600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5939   -2.8369   -1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0724   -3.5069   -0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130   -3.3173    0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903   -2.1281   -1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3920   -2.1439    0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6288    2.0414    0.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0936    1.9160    1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0234    3.2560    0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2677    4.1088    0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1611    2.6644    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7685    0.2910   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
  3 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  2  0
 23  2  1  0
 14  7  1  0
 22 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  9 30  1  0
 13 31  1  0
 16 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.106   2.828   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.336   4.162   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.962   5.569   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       8.075   1.684   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.057   6.814   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.494   5.730   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.944  -4.440   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.390  -4.440   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       6.829   3.842   0.000  0.00  0.00           S+0
HETATM   25  S   UNK     0       2.667  -3.080   0.000  0.00  0.00           S+0
CONECT    1   17                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    9                                                       
CONECT    6    8   15                                                       
CONECT    7    4    9   11                                                  
CONECT    8    6   13   24                                                  
CONECT    9    5    7   25                                                  
CONECT   10   11   12   17                                                  
CONECT   11    7   10   18                                                  
CONECT   12   10   16   19                                                  
CONECT   13    8   20   21                                                  
CONECT   14   15   16   24                                                  
CONECT   15    6   14                                                       
CONECT   16   12   14                                                       
CONECT   17    1   10   25                                                  
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   13                                                            
CONECT   22   25                                                            
CONECT   23   25                                                            
CONECT   24    8   14                                                       
CONECT   25    9   17   22   23                                             
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0060779
HETATM    1  C1  UNL     1      -1.229  -2.799  -0.710  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.699  -1.493  -0.393  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.812  -0.451  -0.057  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.627  -0.736  -0.038  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.139  -1.993  -0.339  1.00  0.00           O  
HETATM    6  N2  UNL     1       1.488   0.176   0.262  1.00  0.00           N  
HETATM    7  C4  UNL     1       2.905  -0.081   0.287  1.00  0.00           C  
HETATM    8  N3  UNL     1       3.534  -1.185   0.669  1.00  0.00           N  
HETATM    9  C5  UNL     1       4.824  -1.240   0.625  1.00  0.00           C  
HETATM   10  C6  UNL     1       5.495  -0.131   0.177  1.00  0.00           C  
HETATM   11  C7  UNL     1       6.949   0.051   0.036  1.00  0.00           C  
HETATM   12  O2  UNL     1       7.752  -0.859   0.337  1.00  0.00           O  
HETATM   13  O3  UNL     1       7.390   1.268  -0.441  1.00  0.00           O  
HETATM   14  S1  UNL     1       4.207   0.938  -0.159  1.00  0.00           S  
HETATM   15  C8  UNL     1      -1.184   0.780   0.246  1.00  0.00           C  
HETATM   16  O4  UNL     1      -0.195   1.735   0.566  1.00  0.00           O  
HETATM   17  C9  UNL     1      -2.551   1.226   0.274  1.00  0.00           C  
HETATM   18  C10 UNL     1      -2.829   2.562   0.612  1.00  0.00           C  
HETATM   19  C11 UNL     1      -4.098   3.074   0.664  1.00  0.00           C  
HETATM   20  C12 UNL     1      -5.175   2.259   0.375  1.00  0.00           C  
HETATM   21  C13 UNL     1      -4.907   0.929   0.039  1.00  0.00           C  
HETATM   22  C14 UNL     1      -3.647   0.453  -0.004  1.00  0.00           C  
HETATM   23  S2  UNL     1      -3.398  -1.211  -0.431  1.00  0.00           S  
HETATM   24  O5  UNL     1      -3.998  -2.059   0.675  1.00  0.00           O  
HETATM   25  O6  UNL     1      -3.994  -1.556  -1.760  1.00  0.00           O  
HETATM   26  H1  UNL     1      -0.594  -2.837  -1.643  1.00  0.00           H  
HETATM   27  H2  UNL     1      -2.072  -3.507  -0.960  1.00  0.00           H  
HETATM   28  H3  UNL     1      -0.713  -3.317   0.143  1.00  0.00           H  
HETATM   29  H4  UNL     1       1.890  -2.128  -1.004  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.392  -2.144   0.935  1.00  0.00           H  
HETATM   31  H6  UNL     1       7.629   2.041   0.186  1.00  0.00           H  
HETATM   32  H7  UNL     1       0.094   1.916   1.510  1.00  0.00           H  
HETATM   33  H8  UNL     1      -2.023   3.256   0.850  1.00  0.00           H  
HETATM   34  H9  UNL     1      -4.268   4.109   0.928  1.00  0.00           H  
HETATM   35  H10 UNL     1      -6.161   2.664   0.418  1.00  0.00           H  
HETATM   36  H11 UNL     1      -5.769   0.291  -0.188  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   23
CONECT    3    4   15   15
CONECT    4    5    6    6
CONECT    5   29
CONECT    6    7
CONECT    7    8    8   14
CONECT    8    9
CONECT    9   10   10   30
CONECT   10   11   14
CONECT   11   12   12   13
CONECT   13   31
CONECT   15   16   17
CONECT   16   32
CONECT   17   18   18   22
CONECT   18   19   33
CONECT   19   20   20   34
CONECT   20   21   35
CONECT   21   22   22   36
CONECT   22   23
CONECT   23   24   24   25   25
END

HMDB0060779
     RDKit          3D
5'-Carboxy meloxicam
 36 38  0  0  0  0  0  0  0  0999 V2000
   -1.2289   -2.7994   -0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6992   -1.4931   -0.3934 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120   -0.4511   -0.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6274   -0.7356   -0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1395   -1.9931   -0.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878    0.1761    0.2621 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9051   -0.0810    0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5340   -1.1846    0.6688 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8238   -1.2399    0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4955   -0.1307    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9495    0.0506    0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7518   -0.8594    0.3365 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3901    1.2679   -0.4410 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2071    0.9377   -0.1585 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840    0.7798    0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1948    1.7353    0.5659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5507    1.2262    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291    2.5617    0.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0983    3.0735    0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1753    2.2587    0.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9072    0.9294    0.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466    0.4535   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980   -1.2113   -0.4308 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.9984   -2.0591    0.6752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9938   -1.5564   -1.7600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5939   -2.8369   -1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0724   -3.5069   -0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130   -3.3173    0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903   -2.1281   -1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3920   -2.1439    0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6288    2.0414    0.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0936    1.9160    1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0234    3.2560    0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2677    4.1088    0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1611    2.6644    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7685    0.2910   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
  3 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  2  0
 23  2  1  0
 14  7  1  0
 22 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  9 30  1  0
 13 31  1  0
 16 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₁₁N₃O₆S₂

Average Molecular Weight

381.384

Monoisotopic Molecular Weight

381.008926479

IUPAC Name

2-{[hydroxy(4-hydroxy-2-methyl-1,1-dioxo-2H-1λ⁶,2-benzothiazin-3-yl)methylidene]amino}-1,3-thiazole-5-carboxylic acid

Traditional Name

2-{[hydroxy(4-hydroxy-2-methyl-1,1-dioxo-1λ⁶,2-benzothiazin-3-yl)methylidene]amino}-1,3-thiazole-5-carboxylic acid

CAS Registry Number

130262-93-0

SMILES

CN1C(C(O)=NC2=NC=C(S2)C(O)=O)=C(O)C2=CC=CC=C2S1(=O)=O

InChI Identifier

InChI=1S/C14H11N3O6S2/c1-17-10(12(19)16-14-15-6-8(24-14)13(20)21)11(18)7-4-2-3-5-9(7)25(17,22)23/h2-6,18H,1H3,(H,20,21)(H,15,16,19)

InChI Key

MTQQFYLGAZXHTB-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

Benzothiazine
Thiazolecarboxylic acid or derivatives
2,5-disubstituted 1,3-thiazole
Ortho-thiazine
Organosulfonic acid amide
Benzenoid
Azole
Organic sulfonic acid or derivatives
Heteroaromatic compound
Organosulfonic acid or derivatives
Thiazole
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060779)
Liver (HMDB: HMDB0060779)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060779)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060779)

Cellular substructure

Cytoplasm (HMDB: HMDB0060779)

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	0.13 g/L	ALOGPS
logP	0.89	ALOGPS
logP	1.47	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	3.83	ChemAxon
pKa (Strongest Basic)	-0.12	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.39 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	91.36 m³·mol⁻¹	ChemAxon
Polarizability	35.59 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]+	184.586	31661259
DarkChem	[M-H]-	178.734	31661259
DeepCCS	[M+H]+	177.251	30932474
DeepCCS	[M-H]-	174.893	30932474
DeepCCS	[M-2H]-	208.701	30932474
DeepCCS	[M+Na]+	183.928	30932474
AllCCS	[M+H]+	182.7	32859911
AllCCS	[M+H-H2O]+	179.8	32859911
AllCCS	[M+NH4]+	185.3	32859911
AllCCS	[M+Na]+	186.0	32859911
AllCCS	[M-H]-	178.1	32859911
AllCCS	[M+Na-2H]-	177.8	32859911
AllCCS	[M+HCOO]-	177.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5'-Carboxy meloxicam	CN1C(C(O)=NC2=NC=C(S2)C(O)=O)=C(O)C2=CC=CC=C2S1(=O)=O	5279.4	Standard polar	33892256
5'-Carboxy meloxicam	CN1C(C(O)=NC2=NC=C(S2)C(O)=O)=C(O)C2=CC=CC=C2S1(=O)=O	2929.4	Standard non polar	33892256
5'-Carboxy meloxicam	CN1C(C(O)=NC2=NC=C(S2)C(O)=O)=C(O)C2=CC=CC=C2S1(=O)=O	3352.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5'-Carboxy meloxicam,1TMS,isomer #1	CN1C(C(=NC2=NC=C(C(=O)O)S2)O[Si](C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O	3294.7	Semi standard non polar	33892256
5'-Carboxy meloxicam,1TMS,isomer #2	CN1C(C(O)=NC2=NC=C(C(=O)O[Si](C)(C)C)S2)=C(O)C2=CC=CC=C2S1(=O)=O	3257.1	Semi standard non polar	33892256
5'-Carboxy meloxicam,1TMS,isomer #3	CN1C(C(O)=NC2=NC=C(C(=O)O)S2)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O	3258.7	Semi standard non polar	33892256
5'-Carboxy meloxicam,2TMS,isomer #1	CN1C(C(=NC2=NC=C(C(=O)O[Si](C)(C)C)S2)O[Si](C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O	3190.3	Semi standard non polar	33892256
5'-Carboxy meloxicam,2TMS,isomer #2	CN1C(C(=NC2=NC=C(C(=O)O)S2)O[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O	3217.5	Semi standard non polar	33892256
5'-Carboxy meloxicam,2TMS,isomer #3	CN1C(C(O)=NC2=NC=C(C(=O)O[Si](C)(C)C)S2)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O	3176.3	Semi standard non polar	33892256
5'-Carboxy meloxicam,3TMS,isomer #1	CN1C(C(=NC2=NC=C(C(=O)O[Si](C)(C)C)S2)O[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O	3182.3	Semi standard non polar	33892256
5'-Carboxy meloxicam,1TBDMS,isomer #1	CN1C(C(=NC2=NC=C(C(=O)O)S2)O[Si](C)(C)C(C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O	3489.0	Semi standard non polar	33892256
5'-Carboxy meloxicam,1TBDMS,isomer #2	CN1C(C(O)=NC2=NC=C(C(=O)O[Si](C)(C)C(C)(C)C)S2)=C(O)C2=CC=CC=C2S1(=O)=O	3489.6	Semi standard non polar	33892256
5'-Carboxy meloxicam,1TBDMS,isomer #3	CN1C(C(O)=NC2=NC=C(C(=O)O)S2)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O	3529.4	Semi standard non polar	33892256
5'-Carboxy meloxicam,2TBDMS,isomer #1	CN1C(C(=NC2=NC=C(C(=O)O[Si](C)(C)C(C)(C)C)S2)O[Si](C)(C)C(C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O	3547.5	Semi standard non polar	33892256
5'-Carboxy meloxicam,2TBDMS,isomer #2	CN1C(C(=NC2=NC=C(C(=O)O)S2)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O	3570.5	Semi standard non polar	33892256
5'-Carboxy meloxicam,2TBDMS,isomer #3	CN1C(C(O)=NC2=NC=C(C(=O)O[Si](C)(C)C(C)(C)C)S2)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O	3610.8	Semi standard non polar	33892256
5'-Carboxy meloxicam,3TBDMS,isomer #1	CN1C(C(=NC2=NC=C(C(=O)O[Si](C)(C)C(C)(C)C)S2)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O	3692.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Carboxy meloxicam GC-MS (Non-derivatized) - 70eV, Positive	splash10-02t9-2932000000-a7f0bc66589a977f5c96	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Carboxy meloxicam GC-MS (3 TMS) - 70eV, Positive	splash10-052f-4594170000-4caefc4adc0213653d21	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Carboxy meloxicam 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'-Carboxy meloxicam 10V, Positive-QTOF	splash10-01q9-0109000000-a7b6e9c00ccea2df2f96	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy meloxicam 20V, Positive-QTOF	splash10-007c-1936000000-cc63492ec1c1e61116e6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy meloxicam 40V, Positive-QTOF	splash10-056r-6910000000-36e28f499c5c410f492b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy meloxicam 10V, Negative-QTOF	splash10-001r-0009000000-126e6e703db8bc725366	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy meloxicam 20V, Negative-QTOF	splash10-00kr-1119000000-1085bb9f62d0f13840d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy meloxicam 40V, Negative-QTOF	splash10-00mo-6930000000-705bd97f5b8b0422fb09	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy meloxicam 10V, Positive-QTOF	splash10-001i-0009000000-a1877301d8a32e07c5ea	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy meloxicam 20V, Positive-QTOF	splash10-001i-0609000000-45afd520ea8b6b07780e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy meloxicam 40V, Positive-QTOF	splash10-0002-1931000000-3ddee2f0cf4cb0d942ba	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy meloxicam 10V, Negative-QTOF	splash10-00y0-0349000000-5ff75115493f64d6436c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy meloxicam 20V, Negative-QTOF	splash10-00dm-1931000000-b61589e257ebef84fc0e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy meloxicam 40V, Negative-QTOF	splash10-00e9-5893000000-c9a8c2f7ecacca2cdcdc	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

54750414

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'-Carboxy meloxicam (HMDB0060779)

MOL for HMDB0060779 (5'-Carboxy meloxicam)

3D MOL for HMDB0060779 (5'-Carboxy meloxicam)

3D SDF for HMDB0060779 (5'-Carboxy meloxicam)

3D-SDF for HMDB0060779 (5'-Carboxy meloxicam)

PDB for HMDB0060779 (5'-Carboxy meloxicam)

3D PDB for HMDB0060779 (5'-Carboxy meloxicam)

SMILES for HMDB0060779 (5'-Carboxy meloxicam)

INCHI for HMDB0060779 (5'-Carboxy meloxicam)

Structure for HMDB0060779 (5'-Carboxy meloxicam)

3D Structure for HMDB0060779 (5'-Carboxy meloxicam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra