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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-22 19:49:56 UTC

Update Date

2021-09-14 15:43:11 UTC

HMDB ID

HMDB0061132

Secondary Accession Numbers

HMDB61132

Metabolite Identification

Common Name

Celecoxib glucuronide

Description

Celecoxib glucuronide is a metabolite of celecoxib and is only found in individuals that have used or taken this drug (PMID: 10681375 ). Celecoxib (trade name: Celebrex) is a sulfa non-steroidal anti-inflammatory drug (NSAID) and selective COX-2 inhibitor used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation, and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis. It is marketed by Pfizer. Celecoxib is available by prescription in capsule form (Wikipedia).

Structure

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


  Mrv1652311011915432D          

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M  END

HMDB0061132
     RDKit          3D
Celecoxib glucuronide
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M  END


  Mrv1652311011915432D          

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M  END
> <DATABASE_ID>
HMDB0061132

> <DATABASE_NAME>
hmdb

> <SMILES>
NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(C=C1)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C23H20F3N3O10S/c24-23(25,26)15-9-14(29(28-15)12-5-7-13(8-6-12)40(27,36)37)10-1-3-11(4-2-10)21(35)39-22-18(32)16(30)17(31)19(38-22)20(33)34/h1-9,16-19,22,30-32H,(H,33,34)(H2,27,36,37)/t16-,17-,18+,19-,22-/m0/s1

> <INCHI_KEY>
ZSTBSABHKHAHNU-QUXXCFOZSA-N

> <FORMULA>
C23H20F3N3O10S

> <MOLECULAR_WEIGHT>
587.48

> <EXACT_MASS>
587.082149519

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
52.38032576688269

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[1-(4-sulfamoylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]benzoyloxy}oxane-2-carboxylic acid

> <JCHEM_LOGP>
1.4058097376666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.686857497885596

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.173421475053044

> <JCHEM_PKA_STRONGEST_BASIC>
-0.002583535768856726

> <JCHEM_POLAR_SURFACE_AREA>
211.49999999999997

> <JCHEM_REFRACTIVITY>
126.74779999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[2-(4-sulfamoylphenyl)-5-(trifluoromethyl)pyrazol-3-yl]benzoyloxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061132
     RDKit          3D
Celecoxib glucuronide
 60 63  0  0  0  0  0  0  0  0999 V2000
   -6.1343    0.7963   -4.2017 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0738   -0.0574   -3.0465 S   0  0  0  0  0  6  0  0  0  0  0  0
   -8.3113    0.7493   -2.7474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5014   -1.4066   -3.5762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1568   -0.2245   -1.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4456   -1.3532   -1.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7496   -1.4254   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7272   -0.3919    0.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0483   -0.4792    2.1399 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6778   -0.7410    3.3053 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8437   -0.8002    4.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2215   -1.0802    5.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7869   -2.3378    5.7732 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1660   -0.1760    6.1649 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0845   -1.0989    6.5336 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5953   -0.5670    3.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7602   -0.3674    2.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6398   -0.1291    1.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3443   -0.2685    2.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7786   -0.0586    1.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6227    0.3161   -0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8374    0.4974   -0.8777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7182    0.8509   -2.0736 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0931    0.2921   -0.3636 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838    0.4346   -1.0664 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9486   -0.8131   -1.0863 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0611   -0.8069   -1.8865 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7400   -2.1197   -1.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7680   -2.3408   -2.4358 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2157   -3.0970   -0.9607 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0756    0.2383   -1.4720 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0303    0.3177   -2.4987 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4162    1.5929   -1.2625 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3858    2.4182   -0.6931 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2452    1.3884   -0.3465 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6028    2.5823   -0.0340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6369    0.4667   -0.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7461    0.2433    0.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4438    0.7523    0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1405    0.8291   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3772    1.8268   -4.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1211    0.6446   -4.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4419   -2.1926   -1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1890   -2.3294    0.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6673   -0.5362    4.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1921   -0.5593    3.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7882   -0.1760    1.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0947    0.7353   -2.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7361   -0.5896   -2.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2514   -2.9932   -0.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5255   -0.0638   -0.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8015    0.8323   -2.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0316    1.9902   -2.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1513    2.5684    0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5890    0.8414    0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0281    2.9228    0.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817    0.7654   -1.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6904    0.3948   -0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4260    1.5716    1.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6981    1.7207   -0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 27 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 21 37  1  0
 37 38  2  0
  8 39  1  0
 39 40  2  0
 40  5  1  0
 17  9  1  0
 38 18  1  0
 35 25  1  0
  1 41  1  0
  1 42  1  0
  6 43  1  0
  7 44  1  0
 16 45  1  0
 19 46  1  0
 20 47  1  0
 25 48  1  6
 27 49  1  6
 30 50  1  0
 31 51  1  1
 32 52  1  0
 33 53  1  6
 34 54  1  0
 35 55  1  1
 36 56  1  0
 37 57  1  0
 38 58  1  0
 39 59  1  0
 40 60  1  0
M  END

HEADER    PROTEIN                                 01-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-NOV-19         0                                  
HETATM    1  S   UNK     0       6.001  -4.502   0.000  0.00  0.00           S+0
HETATM    2  F   UNK     0       3.080   4.368   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       5.572   6.179   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0       3.421   6.520   0.000  0.00  0.00           F+0
HETATM    5  O   UNK     0       7.541  -4.502   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.461  -4.502   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       6.001   1.658   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.755   2.563   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       6.001  -6.042   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.247   2.563   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.001   0.118   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.712   2.087   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.771   4.028   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.231   4.028   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.335  -0.652   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.668  -0.652   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.001  -2.962   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.032   0.581   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.856   3.118   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.335  -2.192   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.668  -2.192   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.641   1.135   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.497   0.105   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.321   2.642   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.326   5.274   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.106   0.660   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.195   1.749   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      13.465  -0.838   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      15.682   1.350   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.158  -0.114   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      17.664  -0.435   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      18.695   0.710   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.219   2.174   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.713   2.494   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      19.250   3.319   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      18.140  -1.899   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      16.237   3.959   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      20.201   0.389   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      17.110  -3.044   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      19.647  -2.219   0.000  0.00  0.00           O+0
CONECT    1    5    6    9   17                                             
CONECT    2   25                                                            
CONECT    3   25                                                            
CONECT    4   25                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    8   10   11                                                  
CONECT    8    7   14                                                       
CONECT    9    1                                                            
CONECT   10    7   12   13                                                  
CONECT   11    7   15   16                                                  
CONECT   12   10   18   19                                                  
CONECT   13   10   14                                                       
CONECT   14    8   13   25                                                  
CONECT   15   11   20                                                       
CONECT   16   11   21                                                       
CONECT   17    1   20   21                                                  
CONECT   18   12   23                                                       
CONECT   19   12   24                                                       
CONECT   20   15   17                                                       
CONECT   21   16   17                                                       
CONECT   22   23   24   26                                                  
CONECT   23   18   22                                                       
CONECT   24   19   22                                                       
CONECT   25    2    3    4   14                                             
CONECT   26   22   27   28                                                  
CONECT   27   26   29                                                       
CONECT   28   26                                                            
CONECT   29   34   30   27                                                  
CONECT   30   31   29                                                       
CONECT   31   32   30   36                                                  
CONECT   32   31   33   38                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33   29   37                                                  
CONECT   35   33                                                            
CONECT   36   31   40   39                                                  
CONECT   37   34                                                            
CONECT   38   32                                                            
CONECT   39   36                                                            
CONECT   40   36                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

COMPND    HMDB0061132
HETATM    1  N1  UNL     1      -6.134   0.796  -4.202  1.00  0.00           N  
HETATM    2  S1  UNL     1      -7.074  -0.057  -3.046  1.00  0.00           S  
HETATM    3  O1  UNL     1      -8.311   0.749  -2.747  1.00  0.00           O  
HETATM    4  O2  UNL     1      -7.501  -1.407  -3.576  1.00  0.00           O  
HETATM    5  C1  UNL     1      -6.157  -0.225  -1.555  1.00  0.00           C  
HETATM    6  C2  UNL     1      -5.446  -1.353  -1.218  1.00  0.00           C  
HETATM    7  C3  UNL     1      -4.750  -1.425  -0.024  1.00  0.00           C  
HETATM    8  C4  UNL     1      -4.727  -0.392   0.881  1.00  0.00           C  
HETATM    9  N2  UNL     1      -4.048  -0.479   2.140  1.00  0.00           N  
HETATM   10  N3  UNL     1      -4.678  -0.741   3.305  1.00  0.00           N  
HETATM   11  C5  UNL     1      -3.844  -0.800   4.325  1.00  0.00           C  
HETATM   12  C6  UNL     1      -4.222  -1.080   5.760  1.00  0.00           C  
HETATM   13  F1  UNL     1      -4.787  -2.338   5.773  1.00  0.00           F  
HETATM   14  F2  UNL     1      -5.166  -0.176   6.165  1.00  0.00           F  
HETATM   15  F3  UNL     1      -3.084  -1.099   6.534  1.00  0.00           F  
HETATM   16  C7  UNL     1      -2.595  -0.567   3.825  1.00  0.00           C  
HETATM   17  C8  UNL     1      -2.760  -0.367   2.442  1.00  0.00           C  
HETATM   18  C9  UNL     1      -1.640  -0.129   1.531  1.00  0.00           C  
HETATM   19  C10 UNL     1      -0.344  -0.269   2.009  1.00  0.00           C  
HETATM   20  C11 UNL     1       0.779  -0.059   1.248  1.00  0.00           C  
HETATM   21  C12 UNL     1       0.623   0.316  -0.082  1.00  0.00           C  
HETATM   22  C13 UNL     1       1.837   0.497  -0.878  1.00  0.00           C  
HETATM   23  O3  UNL     1       1.718   0.851  -2.074  1.00  0.00           O  
HETATM   24  O4  UNL     1       3.093   0.292  -0.364  1.00  0.00           O  
HETATM   25  C14 UNL     1       4.284   0.435  -1.066  1.00  0.00           C  
HETATM   26  O5  UNL     1       4.949  -0.813  -1.086  1.00  0.00           O  
HETATM   27  C15 UNL     1       6.061  -0.807  -1.887  1.00  0.00           C  
HETATM   28  C16 UNL     1       6.740  -2.120  -1.786  1.00  0.00           C  
HETATM   29  O6  UNL     1       7.768  -2.341  -2.436  1.00  0.00           O  
HETATM   30  O7  UNL     1       6.216  -3.097  -0.961  1.00  0.00           O  
HETATM   31  C17 UNL     1       7.076   0.238  -1.472  1.00  0.00           C  
HETATM   32  O8  UNL     1       8.030   0.318  -2.499  1.00  0.00           O  
HETATM   33  C18 UNL     1       6.416   1.593  -1.263  1.00  0.00           C  
HETATM   34  O9  UNL     1       7.386   2.418  -0.693  1.00  0.00           O  
HETATM   35  C19 UNL     1       5.245   1.388  -0.346  1.00  0.00           C  
HETATM   36  O10 UNL     1       4.603   2.582  -0.034  1.00  0.00           O  
HETATM   37  C20 UNL     1      -0.637   0.467  -0.592  1.00  0.00           C  
HETATM   38  C21 UNL     1      -1.746   0.243   0.218  1.00  0.00           C  
HETATM   39  C22 UNL     1      -5.444   0.752   0.545  1.00  0.00           C  
HETATM   40  C23 UNL     1      -6.141   0.829  -0.646  1.00  0.00           C  
HETATM   41  H1  UNL     1      -6.377   1.827  -4.173  1.00  0.00           H  
HETATM   42  H2  UNL     1      -5.121   0.645  -4.140  1.00  0.00           H  
HETATM   43  H3  UNL     1      -5.442  -2.193  -1.916  1.00  0.00           H  
HETATM   44  H4  UNL     1      -4.189  -2.329   0.233  1.00  0.00           H  
HETATM   45  H5  UNL     1      -1.667  -0.536   4.358  1.00  0.00           H  
HETATM   46  H6  UNL     1      -0.192  -0.559   3.030  1.00  0.00           H  
HETATM   47  H7  UNL     1       1.788  -0.176   1.654  1.00  0.00           H  
HETATM   48  H8  UNL     1       4.095   0.735  -2.102  1.00  0.00           H  
HETATM   49  H9  UNL     1       5.736  -0.590  -2.946  1.00  0.00           H  
HETATM   50  H10 UNL     1       5.251  -2.993  -0.603  1.00  0.00           H  
HETATM   51  H11 UNL     1       7.525  -0.064  -0.504  1.00  0.00           H  
HETATM   52  H12 UNL     1       8.801   0.832  -2.152  1.00  0.00           H  
HETATM   53  H13 UNL     1       6.032   1.990  -2.219  1.00  0.00           H  
HETATM   54  H14 UNL     1       7.151   2.568   0.267  1.00  0.00           H  
HETATM   55  H15 UNL     1       5.589   0.841   0.570  1.00  0.00           H  
HETATM   56  H16 UNL     1       5.028   2.923   0.788  1.00  0.00           H  
HETATM   57  H17 UNL     1      -0.782   0.765  -1.636  1.00  0.00           H  
HETATM   58  H18 UNL     1      -2.690   0.395  -0.228  1.00  0.00           H  
HETATM   59  H19 UNL     1      -5.426   1.572   1.257  1.00  0.00           H  
HETATM   60  H20 UNL     1      -6.698   1.721  -0.905  1.00  0.00           H  
CONECT    1    2   41   42
CONECT    2    3    3    4    4
CONECT    2    5
CONECT    5    6    6   40
CONECT    6    7   43
CONECT    7    8    8   44
CONECT    8    9   39
CONECT    9   10   17
CONECT   10   11   11
CONECT   11   12   16
CONECT   12   13   14   15
CONECT   16   17   17   45
CONECT   17   18
CONECT   18   19   19   38
CONECT   19   20   46
CONECT   20   21   21   47
CONECT   21   22   37
CONECT   22   23   23   24
CONECT   24   25
CONECT   25   26   35   48
CONECT   26   27
CONECT   27   28   31   49
CONECT   28   29   29   30
CONECT   30   50
CONECT   31   32   33   51
CONECT   32   52
CONECT   33   34   35   53
CONECT   34   54
CONECT   35   36   55
CONECT   36   56
CONECT   37   38   38   57
CONECT   38   58
CONECT   39   40   40   59
CONECT   40   60
END

HMDB0061132
     RDKit          3D
Celecoxib glucuronide
 60 63  0  0  0  0  0  0  0  0999 V2000
   -6.1343    0.7963   -4.2017 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0738   -0.0574   -3.0465 S   0  0  0  0  0  6  0  0  0  0  0  0
   -8.3113    0.7493   -2.7474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5014   -1.4066   -3.5762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1568   -0.2245   -1.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4456   -1.3532   -1.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7496   -1.4254   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7272   -0.3919    0.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0483   -0.4792    2.1399 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6778   -0.7410    3.3053 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8437   -0.8002    4.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2215   -1.0802    5.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7869   -2.3378    5.7732 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1660   -0.1760    6.1649 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0845   -1.0989    6.5336 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5953   -0.5670    3.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7602   -0.3674    2.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6398   -0.1291    1.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3443   -0.2685    2.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7786   -0.0586    1.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6227    0.3161   -0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8374    0.4974   -0.8777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7182    0.8509   -2.0736 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0931    0.2921   -0.3636 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838    0.4346   -1.0664 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9486   -0.8131   -1.0863 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0611   -0.8069   -1.8865 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7400   -2.1197   -1.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7680   -2.3408   -2.4358 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2157   -3.0970   -0.9607 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0756    0.2383   -1.4720 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0303    0.3177   -2.4987 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4162    1.5929   -1.2625 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3858    2.4182   -0.6931 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2452    1.3884   -0.3465 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6028    2.5823   -0.0340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6369    0.4667   -0.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7461    0.2433    0.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4438    0.7523    0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1405    0.8291   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3772    1.8268   -4.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1211    0.6446   -4.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4419   -2.1926   -1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1890   -2.3294    0.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6673   -0.5362    4.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1921   -0.5593    3.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7882   -0.1760    1.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0947    0.7353   -2.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7361   -0.5896   -2.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2514   -2.9932   -0.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5255   -0.0638   -0.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8015    0.8323   -2.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0316    1.9902   -2.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1513    2.5684    0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5890    0.8414    0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0281    2.9228    0.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817    0.7654   -1.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6904    0.3948   -0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4260    1.5716    1.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6981    1.7207   -0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 27 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 21 37  1  0
 37 38  2  0
  8 39  1  0
 39 40  2  0
 40  5  1  0
 17  9  1  0
 38 18  1  0
 35 25  1  0
  1 41  1  0
  1 42  1  0
  6 43  1  0
  7 44  1  0
 16 45  1  0
 19 46  1  0
 20 47  1  0
 25 48  1  6
 27 49  1  6
 30 50  1  0
 31 51  1  1
 32 52  1  0
 33 53  1  6
 34 54  1  0
 35 55  1  1
 36 56  1  0
 37 57  1  0
 38 58  1  0
 39 59  1  0
 40 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Celecoxib beta-D-glucopyranuronide	HMDB
Celecoxib glucuronide	HMDB
Celecoxib β-D-glucopyranuronide	HMDB

Chemical Formula

C₂₃H₂₀F₃N₃O₁₀S

Average Molecular Weight

587.48

Monoisotopic Molecular Weight

587.082149519

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[1-(4-sulfamoylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]benzoyloxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[2-(4-sulfamoylphenyl)-5-(trifluoromethyl)pyrazol-3-yl]benzoyloxy}oxane-2-carboxylic acid

CAS Registry Number

264236-79-5

SMILES

NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(C=C1)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C(F)(F)F

InChI Identifier

InChI=1S/C23H20F3N3O10S/c24-23(25,26)15-9-14(29(28-15)12-5-7-13(8-6-12)40(27,36)37)10-1-3-11(4-2-10)21(35)39-22-18(32)16(30)17(31)19(38-22)20(33)34/h1-9,16-19,22,30-32H,(H,33,34)(H2,27,36,37)/t16-,17-,18+,19-,22-/m0/s1

InChI Key

ZSTBSABHKHAHNU-QUXXCFOZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

O-glucuronide
1-o-glucuronide
Phenylpyrazole
Benzenesulfonamide
Benzoate ester
Benzoic acid or derivatives
Benzenesulfonyl group
Benzoyl
Beta-hydroxy acid
Benzenoid
Monosaccharide
Hydroxy acid
Organosulfonic acid amide
Dicarboxylic acid or derivatives
Oxane
Monocyclic benzene moiety
Pyran
Azole
Heteroaromatic compound
Aminosulfonyl compound
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Pyrazole
Secondary alcohol
Carboxylic acid ester
Polyol
Acetal
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organoheterocyclic compound
Carbonyl group
Organohalogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organosulfur compound
Organonitrogen compound
Organofluoride
Alkyl fluoride
Alkyl halide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Liver (HMDB: HMDB0061132)
Kidney (HMDB: HMDB0061132)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061132)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061132)

Cellular substructure

Cytoplasm (HMDB: HMDB0061132)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Celecoxib Action Pathway (PathBank: SMP0000096)

Metabolic pathway

Celecoxib Metabolism Pathway (PathBank: SMP0000644)

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	0.053 g/L	ALOGPS
logP	1.41	ChemAxon
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	-0.0026	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	211.5 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	126.75 m³·mol⁻¹	ChemAxon
Polarizability	52.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	208.103	30932474
DeepCCS	[M-H]-	206.278	30932474
DeepCCS	[M-2H]-	239.844	30932474
DeepCCS	[M+Na]+	213.709	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Celecoxib glucuronide	NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(C=C1)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C(F)(F)F	6795.4	Standard polar	33892256
Celecoxib glucuronide	NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(C=C1)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C(F)(F)F	4069.1	Standard non polar	33892256
Celecoxib glucuronide	NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(C=C1)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C(F)(F)F	4571.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Celecoxib glucuronide,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O)[C@H]1O	4412.9	Semi standard non polar	33892256
Celecoxib glucuronide,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)O[C@H](C(=O)O)[C@H]1O	4406.2	Semi standard non polar	33892256
Celecoxib glucuronide,1TMS,isomer #3	C[Si](C)(C)O[C@H]1[C@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)O[C@H](C(=O)O)[C@@H](O)[C@@H]1O	4415.8	Semi standard non polar	33892256
Celecoxib glucuronide,1TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O)[C@@H](O)[C@@H]1O	4374.1	Semi standard non polar	33892256
Celecoxib glucuronide,1TMS,isomer #5	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)C=C2)C=C1	4449.4	Semi standard non polar	33892256
Celecoxib glucuronide,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	4364.0	Semi standard non polar	33892256
Celecoxib glucuronide,2TMS,isomer #10	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]3O)C=C2)C=C1	4375.4	Semi standard non polar	33892256
Celecoxib glucuronide,2TMS,isomer #11	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)C=C2)C=C1	4412.4	Semi standard non polar	33892256
Celecoxib glucuronide,2TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O[Si](C)(C)C)[C@H]1O	4398.8	Semi standard non polar	33892256
Celecoxib glucuronide,2TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O)[C@H]1O[Si](C)(C)C	4387.6	Semi standard non polar	33892256
Celecoxib glucuronide,2TMS,isomer #4	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]3O)C=C2)C=C1	4391.9	Semi standard non polar	33892256
Celecoxib glucuronide,2TMS,isomer #5	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](C(=O)O)O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@@H]1O[Si](C)(C)C	4390.1	Semi standard non polar	33892256
Celecoxib glucuronide,2TMS,isomer #6	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	4345.9	Semi standard non polar	33892256
Celecoxib glucuronide,2TMS,isomer #7	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O)C=C2)C=C1	4387.1	Semi standard non polar	33892256
Celecoxib glucuronide,2TMS,isomer #8	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	4358.7	Semi standard non polar	33892256
Celecoxib glucuronide,2TMS,isomer #9	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O[Si](C)(C)C)C=C2)C=C1	4392.5	Semi standard non polar	33892256
Celecoxib glucuronide,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	4376.5	Semi standard non polar	33892256
Celecoxib glucuronide,3TMS,isomer #10	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O)C=C2)C=C1	4352.8	Semi standard non polar	33892256
Celecoxib glucuronide,3TMS,isomer #11	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C3)C=C2)O[C@H](C(=O)O)[C@H]1O	4387.1	Semi standard non polar	33892256
Celecoxib glucuronide,3TMS,isomer #12	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]3O[Si](C)(C)C)C=C2)C=C1	4356.6	Semi standard non polar	33892256
Celecoxib glucuronide,3TMS,isomer #13	C[Si](C)(C)O[C@H]1[C@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C3)C=C2)O[C@H](C(=O)O)[C@@H](O)[C@@H]1O	4392.7	Semi standard non polar	33892256
Celecoxib glucuronide,3TMS,isomer #14	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C3)C=C2)[C@H](O)[C@@H](O)[C@@H]1O	4373.4	Semi standard non polar	33892256
Celecoxib glucuronide,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	4370.7	Semi standard non polar	33892256
Celecoxib glucuronide,3TMS,isomer #3	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]3O)C=C2)C=C1	4372.0	Semi standard non polar	33892256
Celecoxib glucuronide,3TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)O[C@H](C(=O)O)[C@H]1O[Si](C)(C)C	4407.6	Semi standard non polar	33892256
Celecoxib glucuronide,3TMS,isomer #5	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]3O[Si](C)(C)C)C=C2)C=C1	4380.3	Semi standard non polar	33892256
Celecoxib glucuronide,3TMS,isomer #6	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]3O)C=C2)C=C1	4374.1	Semi standard non polar	33892256
Celecoxib glucuronide,3TMS,isomer #7	C[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C3)C=C2)[C@H](O)[C@H]1O	4399.1	Semi standard non polar	33892256
Celecoxib glucuronide,3TMS,isomer #8	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	4369.2	Semi standard non polar	33892256
Celecoxib glucuronide,3TMS,isomer #9	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)C=C2)C=C1	4368.1	Semi standard non polar	33892256
Celecoxib glucuronide,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	4402.5	Semi standard non polar	33892256
Celecoxib glucuronide,4TMS,isomer #10	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C3)C=C2)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	4379.5	Semi standard non polar	33892256
Celecoxib glucuronide,4TMS,isomer #11	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C3)C=C2)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	4380.9	Semi standard non polar	33892256
Celecoxib glucuronide,4TMS,isomer #2	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]3O[Si](C)(C)C)C=C2)C=C1	4377.3	Semi standard non polar	33892256
Celecoxib glucuronide,4TMS,isomer #3	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]3O)C=C2)C=C1	4374.9	Semi standard non polar	33892256
Celecoxib glucuronide,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C3)C=C2)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	4396.4	Semi standard non polar	33892256
Celecoxib glucuronide,4TMS,isomer #5	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)C=C2)C=C1	4403.2	Semi standard non polar	33892256
Celecoxib glucuronide,4TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C3)C=C2)[C@H](O[Si](C)(C)C)[C@H]1O	4399.4	Semi standard non polar	33892256
Celecoxib glucuronide,4TMS,isomer #7	C[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C3)C=C2)[C@H](O)[C@H]1O[Si](C)(C)C	4407.9	Semi standard non polar	33892256
Celecoxib glucuronide,4TMS,isomer #8	C[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)C=C2)C=C1	4371.4	Semi standard non polar	33892256
Celecoxib glucuronide,4TMS,isomer #9	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](C(=O)O)O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C3)C=C2)[C@@H]1O[Si](C)(C)C	4393.9	Semi standard non polar	33892256
Celecoxib glucuronide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O)[C@H]1O	4621.7	Semi standard non polar	33892256
Celecoxib glucuronide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)O[C@H](C(=O)O)[C@H]1O	4623.5	Semi standard non polar	33892256
Celecoxib glucuronide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)O[C@H](C(=O)O)[C@@H](O)[C@@H]1O	4624.6	Semi standard non polar	33892256
Celecoxib glucuronide,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O)[C@@H](O)[C@@H]1O	4614.9	Semi standard non polar	33892256
Celecoxib glucuronide,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)C=C2)C=C1	4672.7	Semi standard non polar	33892256
Celecoxib glucuronide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	4776.1	Semi standard non polar	33892256
Celecoxib glucuronide,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]3O)C=C2)C=C1	4788.5	Semi standard non polar	33892256
Celecoxib glucuronide,2TBDMS,isomer #11	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)C=C2)C=C1	4867.2	Semi standard non polar	33892256
Celecoxib glucuronide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4793.9	Semi standard non polar	33892256
Celecoxib glucuronide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4782.1	Semi standard non polar	33892256
Celecoxib glucuronide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]3O)C=C2)C=C1	4790.1	Semi standard non polar	33892256
Celecoxib glucuronide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](C(=O)O)O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	4773.5	Semi standard non polar	33892256
Celecoxib glucuronide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	4764.3	Semi standard non polar	33892256
Celecoxib glucuronide,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)C=C2)C=C1	4796.1	Semi standard non polar	33892256
Celecoxib glucuronide,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)C2=CC=C(C3=CC(C(F)(F)F)=NN3C3=CC=C(S(N)(=O)=O)C=C3)C=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	4772.4	Semi standard non polar	33892256
Celecoxib glucuronide,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC=C(N2N=C(C(F)(F)F)C=C2C2=CC=C(C(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)C=C2)C=C1	4787.2	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 - Celecoxib glucuronide GC-MS ("Celecoxib glucuronide,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Celecoxib glucuronide GC-MS (TMS_3_8) - 70eV, Positive	Not Available	2021-10-15	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 - Celecoxib glucuronide 10V, Negative-QTOF	splash10-000i-2400390000-47bb7e48ac2fdcf2f248	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celecoxib glucuronide 20V, Negative-QTOF	splash10-03xr-9201740000-26873834942f6c631d21	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celecoxib glucuronide 40V, Negative-QTOF	splash10-07yi-9000230000-e303c394800479e94333	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celecoxib glucuronide 10V, Positive-QTOF	splash10-0006-0309030000-7533ac10582ef03d2b93	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celecoxib glucuronide 20V, Positive-QTOF	splash10-0006-0209110000-43d14aa119944594bf23	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Celecoxib glucuronide 40V, Positive-QTOF	splash10-014l-1329200000-e9bd4849fc82c9d950b2	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Celecoxib Action Pathway		Not Available
Celecoxib Metabolism Pathway		Not Available

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

8591384

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10415951

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

Paulson SK, Hribar JD, Liu NW, Hajdu E, Bible RH Jr, Piergies A, Karim A: Metabolism and excretion of [(14)C]celecoxib in healthy male volunteers. Drug Metab Dispos. 2000 Mar;28(3):308-14. [PubMed:10681375 ]

Showing metabocard for Celecoxib glucuronide (HMDB0061132)

MOL for HMDB0061132 (Celecoxib glucuronide)

3D MOL for HMDB0061132 (Celecoxib glucuronide)

3D SDF for HMDB0061132 (Celecoxib glucuronide)

3D-SDF for HMDB0061132 (Celecoxib glucuronide)

PDB for HMDB0061132 (Celecoxib glucuronide)

3D PDB for HMDB0061132 (Celecoxib glucuronide)

SMILES for HMDB0061132 (Celecoxib glucuronide)

INCHI for HMDB0061132 (Celecoxib glucuronide)

Structure for HMDB0061132 (Celecoxib glucuronide)

3D Structure for HMDB0061132 (Celecoxib glucuronide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra