Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:32:28 UTC

Update Date

2022-11-23 22:13:43 UTC

HMDB ID

HMDB0253714

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isoxicam

Description

Isoxicam, also known as maxicam or BRN 0577221, 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). Based on a literature review a significant number of articles have been published on Isoxicam. This compound has been identified in human blood as reported by (PMID: 31557052 ). Isoxicam is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isoxicam is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0253714
     RDKit          3D
isoxicam
 36 38  0  0  0  0  0  0  0  0999 V2000
    6.5332    0.0372    0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1015   -0.3195    0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1709   -0.1144   -0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728   -0.6065    0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8672   -0.5800   -0.5787 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6496   -1.0664   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6770   -2.2120    0.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6457   -0.3883   -0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7022   -0.9940    0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5660   -2.2735    0.9186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -0.4463    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1025   -1.1826    0.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3840   -0.6995    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6924    0.5331    0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6467    1.2382   -0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611    0.7784   -0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1286    1.7574   -0.9008 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.4268    2.1109   -2.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    3.0112   -0.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6392    0.8900   -0.7825 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5718    1.4473   -1.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2355   -1.0720    1.3163 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4995   -0.8888    1.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1839   -0.8411    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7399    0.8023   -0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8783    0.5139    1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3836    0.3393   -1.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145   -3.0616    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9139   -2.1602    1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1937   -1.2584    1.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6979    0.9204    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8573    2.2080   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137    2.4652   -1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0091    0.9181   -2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029    1.6931   -0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5335   -1.4989    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  2  0
 17 20  1  0
 20 21  1  0
  4 22  1  0
 22 23  1  0
 23  2  1  0
 20  8  1  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 21 33  1  0
 21 34  1  0
 21 35  1  0
 22 36  1  0
M  END


  Mrv0541 05041405412D          

 23 25  0  0  0  0            999 V2000
    5.5156    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    4.3731    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1800    0.9920    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
    4.2868   -0.0000    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
    3.5724   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0405   -0.3356    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
    2.8579    0.8250    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
    5.5925    0.2775    0.0000 O   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
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
 15 11  2  0  0  0  0
 15 14  1  4  0  0  0
 16 11  1  0  0  0  0
 17  2  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  2  0  0  0  0
 22  8  1  0  0  0  0
 22 16  1  0  0  0  0
 23 10  1  0  0  0  0
 23 17  1  0  0  0  0
 23 20  2  0  0  0  0
 23 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253714

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(C(=O)N=C2NOC(C)=C2)=C(O)C2=CC=CC=C2S1(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H13N3O5S/c1-8-7-11(16-22-8)15-14(19)12-13(18)9-5-3-4-6-10(9)23(20,21)17(12)2/h3-7,18H,1-2H3,(H,15,16,19)

> <INCHI_KEY>
YYUAYBYLJSNDCX-UHFFFAOYSA-N

> <FORMULA>
C14H13N3O5S

> <MOLECULAR_WEIGHT>
335.335

> <EXACT_MASS>
335.057591231

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
32.242382047062605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.60

> <JCHEM_LOGP>
-0.08529005333333302

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.97145391906675

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.464686806172876

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9712446597465346

> <JCHEM_POLAR_SURFACE_AREA>
108.3

> <JCHEM_REFRACTIVITY>
94.89979999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
maxicam

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253714
     RDKit          3D
isoxicam
 36 38  0  0  0  0  0  0  0  0999 V2000
    6.5332    0.0372    0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1015   -0.3195    0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1709   -0.1144   -0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728   -0.6065    0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8672   -0.5800   -0.5787 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6496   -1.0664   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6770   -2.2120    0.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6457   -0.3883   -0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7022   -0.9940    0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5660   -2.2735    0.9186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -0.4463    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1025   -1.1826    0.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3840   -0.6995    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6924    0.5331    0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6467    1.2382   -0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611    0.7784   -0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1286    1.7574   -0.9008 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.4268    2.1109   -2.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    3.0112   -0.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6392    0.8900   -0.7825 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5718    1.4473   -1.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2355   -1.0720    1.3163 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4995   -0.8888    1.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1839   -0.8411    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7399    0.8023   -0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8783    0.5139    1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3836    0.3393   -1.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145   -3.0616    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9139   -2.1602    1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1937   -1.2584    1.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6979    0.9204    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8573    2.2080   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137    2.4652   -1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0091    0.9181   -2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029    1.6931   -0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5335   -1.4989    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  2  0
 17 20  1  0
 20 21  1  0
  4 22  1  0
 22 23  1  0
 23  2  1  0
 20  8  1  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 21 33  1  0
 21 34  1  0
 21 35  1  0
 22 36  1  0
M  END

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   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   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
CONECT    1    8                                                            
CONECT    2   17                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    9                                                       
CONECT    6    4   10                                                       
CONECT    7    8   11                                                       
CONECT    8    1    7   22                                                  
CONECT    9    5   10   13                                                  
CONECT   10    6    9   23                                                  
CONECT   11    7   15   16                                                  
CONECT   12   13   14   17                                                  
CONECT   13    9   12   18                                                  
CONECT   14   12   15   19                                                  
CONECT   15   11   14                                                       
CONECT   16   11   22                                                       
CONECT   17    2   12   23                                                  
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   23                                                            
CONECT   21   23                                                            
CONECT   22    8   16                                                       
CONECT   23   10   17   20   21                                             
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0253714
HETATM    1  C1  UNL     1       6.533   0.037   0.513  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.102  -0.320   0.570  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.171  -0.114  -0.416  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.973  -0.606   0.084  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.867  -0.580  -0.579  1.00  0.00           N  
HETATM    6  C5  UNL     1       0.650  -1.066  -0.102  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.677  -2.212   0.441  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.646  -0.388  -0.169  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.702  -0.994   0.333  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.566  -2.274   0.919  1.00  0.00           O  
HETATM   11  C8  UNL     1      -3.042  -0.446   0.338  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.103  -1.183   0.902  1.00  0.00           C  
HETATM   13  C10 UNL     1      -5.384  -0.700   0.927  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.692   0.533   0.398  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.647   1.238  -0.149  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.361   0.778  -0.185  1.00  0.00           C  
HETATM   17  S1  UNL     1      -2.129   1.757  -0.901  1.00  0.00           S  
HETATM   18  O3  UNL     1      -2.427   2.111  -2.329  1.00  0.00           O  
HETATM   19  O4  UNL     1      -2.009   3.011  -0.059  1.00  0.00           O  
HETATM   20  N2  UNL     1      -0.639   0.890  -0.782  1.00  0.00           N  
HETATM   21  C14 UNL     1       0.572   1.447  -1.291  1.00  0.00           C  
HETATM   22  N3  UNL     1       3.235  -1.072   1.316  1.00  0.00           N  
HETATM   23  O5  UNL     1       4.499  -0.889   1.575  1.00  0.00           O  
HETATM   24  H1  UNL     1       7.184  -0.841   0.270  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.740   0.802  -0.286  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.878   0.514   1.464  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.384   0.339  -1.362  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.615  -3.062   0.268  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.914  -2.160   1.333  1.00  0.00           H  
HETATM   30  H7  UNL     1      -6.194  -1.258   1.356  1.00  0.00           H  
HETATM   31  H8  UNL     1      -6.698   0.920   0.413  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.857   2.208  -0.572  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.314   2.465  -1.723  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.009   0.918  -2.162  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.303   1.693  -0.493  1.00  0.00           H  
HETATM   36  H13 UNL     1       2.533  -1.499   1.934  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3   23
CONECT    3    4   27
CONECT    4    5    5   22
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9    9   20
CONECT    9   10   11
CONECT   10   28
CONECT   11   12   12   16
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15   31
CONECT   15   16   16   32
CONECT   16   17
CONECT   17   18   18   19   19
CONECT   17   20
CONECT   20   21
CONECT   21   33   34   35
CONECT   22   23   36
END

HMDB0253714
     RDKit          3D
isoxicam
 36 38  0  0  0  0  0  0  0  0999 V2000
    6.5332    0.0372    0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1015   -0.3195    0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1709   -0.1144   -0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728   -0.6065    0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8672   -0.5800   -0.5787 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6496   -1.0664   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6770   -2.2120    0.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6457   -0.3883   -0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7022   -0.9940    0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5660   -2.2735    0.9186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -0.4463    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1025   -1.1826    0.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3840   -0.6995    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6924    0.5331    0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6467    1.2382   -0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611    0.7784   -0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1286    1.7574   -0.9008 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.4268    2.1109   -2.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    3.0112   -0.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6392    0.8900   -0.7825 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5718    1.4473   -1.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2355   -1.0720    1.3163 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4995   -0.8888    1.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1839   -0.8411    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7399    0.8023   -0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8783    0.5139    1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3836    0.3393   -1.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145   -3.0616    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9139   -2.1602    1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1937   -1.2584    1.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6979    0.9204    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8573    2.2080   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137    2.4652   -1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0091    0.9181   -2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029    1.6931   -0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5335   -1.4989    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  2  0
 17 20  1  0
 20 21  1  0
  4 22  1  0
 22 23  1  0
 23  2  1  0
 20  8  1  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 21 33  1  0
 21 34  1  0
 21 35  1  0
 22 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide	ChEBI
4-Hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-dioxide	ChEBI
BRN 0577221	ChEBI
EINECS 252-084-5	ChEBI
Isoxicamo	ChEBI
Isoxicamum	ChEBI
Maxicam	ChEBI
N-(5-Methyl-3-isoxazolyl)-4-hydroxy-2-methyl-2H-1,2-benzthiazine-3-carboxamide 1,1-dioxide	ChEBI
UNII-8xu734c4NG	ChEBI
W 8495	ChEBI
Vectren	MeSH

Chemical Formula

C₁₄H₁₃N₃O₅S

Average Molecular Weight

335.335

Monoisotopic Molecular Weight

335.057591231

IUPAC Name

4-hydroxy-2-methyl-N-(5-methyl-2,3-dihydro-1,2-oxazol-3-ylidene)-1,1-dioxo-2H-1λ⁶,2-benzothiazine-3-carboxamide

Traditional Name

maxicam

CAS Registry Number

Not Available

SMILES

CN1C(C(=O)N=C2NOC(C)=C2)=C(O)C2=CC=CC=C2S1(=O)=O

InChI Identifier

InChI=1S/C14H13N3O5S/c1-8-7-11(16-22-8)15-14(19)12-13(18)9-5-3-4-6-10(9)23(20,21)17(12)2/h3-7,18H,1-2H3,(H,15,16,19)

InChI Key

YYUAYBYLJSNDCX-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Not Available

Direct Parent

Benzothiazines

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Benzothiazine
Ortho-thiazine
Organosulfonic acid amide
Benzenoid
Azole
Isoxazole
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Vinylogous acid
Heteroaromatic compound
N-acylimine
Carboxylic acid derivative
Azacycle
Oxacycle
Organic oxide
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:76163 )
isoxazoles (CHEBI:76163 )
benzothiazine (CHEBI:76163 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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
logP	0.6	ALOGPS
logP	-0.085	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-0.97	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.9 m³·mol⁻¹	ChemAxon
Polarizability	32.24 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]+	165.864	30932474
DeepCCS	[M-H]-	163.506	30932474
DeepCCS	[M-2H]-	196.489	30932474
DeepCCS	[M+Na]+	171.957	30932474
AllCCS	[M+H]+	175.4	32859911
AllCCS	[M+H-H2O]+	172.1	32859911
AllCCS	[M+NH4]+	178.4	32859911
AllCCS	[M+Na]+	179.3	32859911
AllCCS	[M-H]-	173.3	32859911
AllCCS	[M+Na-2H]-	173.0	32859911
AllCCS	[M+HCOO]-	172.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
isoxicam	CN1C(C(=O)N=C2NOC(C)=C2)=C(O)C2=CC=CC=C2S1(=O)=O	4176.0	Standard polar	33892256
isoxicam	CN1C(C(=O)N=C2NOC(C)=C2)=C(O)C2=CC=CC=C2S1(=O)=O	2859.0	Standard non polar	33892256
isoxicam	CN1C(C(=O)N=C2NOC(C)=C2)=C(O)C2=CC=CC=C2S1(=O)=O	2675.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
isoxicam,2TMS,isomer #1	CC1=CC(=NC(=O)C2=C(O[Si](C)(C)C)C3=CC=CC=C3S(=O)(=O)N2C)N([Si](C)(C)C)O1	2942.1	Semi standard non polar	33892256
isoxicam,2TMS,isomer #1	CC1=CC(=NC(=O)C2=C(O[Si](C)(C)C)C3=CC=CC=C3S(=O)(=O)N2C)N([Si](C)(C)C)O1	2978.1	Standard non polar	33892256
isoxicam,2TMS,isomer #1	CC1=CC(=NC(=O)C2=C(O[Si](C)(C)C)C3=CC=CC=C3S(=O)(=O)N2C)N([Si](C)(C)C)O1	4050.6	Standard polar	33892256
isoxicam,2TBDMS,isomer #1	CC1=CC(=NC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3S(=O)(=O)N2C)N([Si](C)(C)C(C)(C)C)O1	3324.2	Semi standard non polar	33892256
isoxicam,2TBDMS,isomer #1	CC1=CC(=NC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3S(=O)(=O)N2C)N([Si](C)(C)C(C)(C)C)O1	3439.1	Standard non polar	33892256
isoxicam,2TBDMS,isomer #1	CC1=CC(=NC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C3=CC=CC=C3S(=O)(=O)N2C)N([Si](C)(C)C(C)(C)C)O1	4065.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxicam GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-5910000000-59f2ea7557d92ab78864	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxicam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxicam GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxicam GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxicam GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxicam GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoxicam LC-ESI-qTof , Positive-QTOF	splash10-004r-3911000000-ea33aeb4c6cdbcd42af1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoxicam , positive-QTOF	splash10-0hi2-4920000000-6d8f0aecb48174d3dfd1	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxicam 10V, Positive-QTOF	splash10-000j-6139000000-eda17764d6ae14c8ea69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxicam 20V, Positive-QTOF	splash10-0002-9100000000-6a727de849d5762b2236	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxicam 40V, Positive-QTOF	splash10-014l-9100000000-c14c34207cdf213edad8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxicam 10V, Negative-QTOF	splash10-001i-3019000000-80a85d94a87f57b4278e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxicam 20V, Negative-QTOF	splash10-0002-9114000000-b3bac29c6306d4d35c25	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxicam 40V, Negative-QTOF	splash10-000e-9500000000-1aefb087b601b1c5bb27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxicam 10V, Positive-QTOF	splash10-000i-2009000000-ceb60f900f597754c2fe	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxicam 20V, Positive-QTOF	splash10-000j-9116000000-7d5aa59172644fb2653a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxicam 40V, Positive-QTOF	splash10-0002-9210000000-e2893be2258651b2bbac	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxicam 10V, Negative-QTOF	splash10-00di-0393000000-059648ce6bfdbc7bdc9d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxicam 20V, Negative-QTOF	splash10-000b-4592000000-d145fec97cc1a05cdf04	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxicam 40V, Negative-QTOF	splash10-0304-9660000000-20526b055b7fe2f92b6b	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08942

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10442695

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isoxicam

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

76163

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Isoxicam (HMDB0253714)

MOL for HMDB0253714 (Isoxicam)

3D MOL for HMDB0253714 (Isoxicam)

3D SDF for HMDB0253714 (Isoxicam)

3D-SDF for HMDB0253714 (Isoxicam)

PDB for HMDB0253714 (Isoxicam)

3D PDB for HMDB0253714 (Isoxicam)

SMILES for HMDB0253714 (Isoxicam)

INCHI for HMDB0253714 (Isoxicam)

Structure for HMDB0253714 (Isoxicam)

3D Structure for HMDB0253714 (Isoxicam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra