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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015565

Secondary Accession Numbers

HMDB15565

Metabolite Identification

Common Name

Etoricoxib

Description

Etoricoxib, also known as L791456 or MK-663, belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other. Etoricoxib is a drug which is used for the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout. In humans, etoricoxib is involved in the etoricoxib action pathway. Etoricoxib is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on Etoricoxib.

Structure

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

HMDB0015565
     RDKit          3D
Etoricoxib
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.3188   -3.5416    0.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8995   -2.1761    0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9218   -1.1481    1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499    0.1224    1.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1329    0.4115   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7674    1.7986   -0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7156    2.7436   -0.6906 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4329    4.0243   -0.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121    4.3881   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030    6.0775   -1.4363 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1180    3.4765   -0.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4535    2.1371   -0.6634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6762    1.2425   -0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0303    0.2921   -1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1412   -0.5435   -1.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799   -0.3741   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2827   -1.3737    0.2093 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.8947   -2.8659    1.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3104   -0.6258    1.0202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8452   -1.7742   -1.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5480    0.5871    0.8613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4442    1.3838    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1158   -0.6056   -1.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4899   -1.8370   -0.7843 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090   -4.0224   -0.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0604   -3.5201    1.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4461   -4.1087    1.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484   -1.3586    2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5562    0.9490    1.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1736    4.8005   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9092    3.7456   -1.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4557    0.1640   -2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4351   -1.2972   -1.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0130   -3.4015    0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7888   -3.5478    0.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8416   -2.6727    2.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1309    0.7216    1.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023    2.1289    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8045   -0.4000   -2.1744 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  0
  5  6  1  0
  6  7  2  0
  7  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  1  0
 17 19  2  0
 17 20  2  0
 16 21  1  0
 21 22  2  0
  5 23  1  0
 23 24  2  0
 24  2  1  0
 12  6  1  0
 22 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  8 30  1  0
 11 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
M  END

1628
  Mrv0541 02231215362D          

 24 26  0  0  0  0            999 V2000
    6.6513   -2.8875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3973    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0473    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  2  0  0  0  0
  2  9  1  0  0  0  0
  2 17  1  0  0  0  0
  5 10  1  0  0  0  0
  5 21  2  0  0  0  0
  6 20  1  0  0  0  0
  6 23  2  0  0  0  0
  7  8  1  0  0  0  0
  7 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 10  2  0  0  0  0
  8 16  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 15 18  1  0  0  0  0
 15 20  2  0  0  0  0
 16 19  2  0  0  0  0
 18 22  2  0  0  0  0
 19 21  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015565

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NC=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H15ClN2O2S/c1-12-3-4-14(10-20-12)18-17(9-15(19)11-21-18)13-5-7-16(8-6-13)24(2,22)23/h3-11H,1-2H3

> <INCHI_KEY>
MNJVRJDLRVPLFE-UHFFFAOYSA-N

> <FORMULA>
C18H15ClN2O2S

> <MOLECULAR_WEIGHT>
358.842

> <EXACT_MASS>
358.054276131

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.416912303869665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-chloro-3-(4-methanesulfonylphenyl)-2-(6-methylpyridin-3-yl)pyridine

> <ALOGPS_LOGP>
3.70

> <JCHEM_LOGP>
2.7939253993333337

> <ALOGPS_LOGS>
-5.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.69310175275668

> <JCHEM_PKA_STRONGEST_BASIC>
4.960388315113536

> <JCHEM_POLAR_SURFACE_AREA>
59.92

> <JCHEM_REFRACTIVITY>
95.04450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
etoricoxib

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015565
     RDKit          3D
Etoricoxib
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.3188   -3.5416    0.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8995   -2.1761    0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9218   -1.1481    1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499    0.1224    1.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1329    0.4115   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7674    1.7986   -0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7156    2.7436   -0.6906 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4329    4.0243   -0.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121    4.3881   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030    6.0775   -1.4363 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1180    3.4765   -0.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4535    2.1371   -0.6634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6762    1.2425   -0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0303    0.2921   -1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1412   -0.5435   -1.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799   -0.3741   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2827   -1.3737    0.2093 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.8947   -2.8659    1.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3104   -0.6258    1.0202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8452   -1.7742   -1.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5480    0.5871    0.8613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4442    1.3838    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1158   -0.6056   -1.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4899   -1.8370   -0.7843 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090   -4.0224   -0.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0604   -3.5201    1.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4461   -4.1087    1.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484   -1.3586    2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5562    0.9490    1.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1736    4.8005   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9092    3.7456   -1.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4557    0.1640   -2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4351   -1.2972   -1.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0130   -3.4015    0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7888   -3.5478    0.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8416   -2.6727    2.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1309    0.7216    1.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023    2.1289    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8045   -0.4000   -2.1744 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  0
  5  6  1  0
  6  7  2  0
  7  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  1  0
 17 19  2  0
 17 20  2  0
 16 21  1  0
 21 22  2  0
  5 23  1  0
 23 24  2  0
 24  2  1  0
 12  6  1  0
 22 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  8 30  1  0
 11 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1628                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      12.416  -5.390   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0       9.748   3.850   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       8.208   3.850   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.288   3.850   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.415  -4.620   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       5.747   0.000   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.748  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.748  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.082   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.747  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.081  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.748  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.414  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2    3    4    9   17                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5   10   21                                                       
CONECT    6   20   23                                                       
CONECT    7    8   11   12                                                  
CONECT    8    7   10   16                                                  
CONECT    9    2   13   14                                                  
CONECT   10    5    8   15                                                  
CONECT   11    7   13                                                       
CONECT   12    7   14                                                       
CONECT   13    9   11                                                       
CONECT   14    9   12                                                       
CONECT   15   10   18   20                                                  
CONECT   16    8   19                                                       
CONECT   17    2                                                            
CONECT   18   15   22                                                       
CONECT   19    1   16   21                                                  
CONECT   20    6   15                                                       
CONECT   21    5   19                                                       
CONECT   22   18   23                                                       
CONECT   23    6   22   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0015565
HETATM    1  C1  UNL     1       3.319  -3.542   0.851  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.899  -2.176   0.448  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.922  -1.148   1.380  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.550   0.122   1.058  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.133   0.412  -0.245  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.767   1.799  -0.542  1.00  0.00           C  
HETATM    7  N1  UNL     1       2.716   2.744  -0.691  1.00  0.00           N  
HETATM    8  C7  UNL     1       2.433   4.024  -0.957  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.112   4.388  -1.085  1.00  0.00           C  
HETATM   10 CL1  UNL     1       0.703   6.077  -1.436  1.00  0.00          CL  
HETATM   11  C9  UNL     1       0.118   3.476  -0.945  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.454   2.137  -0.663  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.676   1.243  -0.522  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.030   0.292  -1.425  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.141  -0.544  -1.234  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.880  -0.374  -0.085  1.00  0.00           C  
HETATM   17  S1  UNL     1      -4.283  -1.374   0.209  1.00  0.00           S  
HETATM   18  C15 UNL     1      -3.895  -2.866   1.067  1.00  0.00           C  
HETATM   19  O1  UNL     1      -5.310  -0.626   1.020  1.00  0.00           O  
HETATM   20  O2  UNL     1      -4.845  -1.774  -1.142  1.00  0.00           O  
HETATM   21  C16 UNL     1      -2.548   0.587   0.861  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.444   1.384   0.625  1.00  0.00           C  
HETATM   23  C18 UNL     1       2.116  -0.606  -1.150  1.00  0.00           C  
HETATM   24  N2  UNL     1       2.490  -1.837  -0.784  1.00  0.00           N  
HETATM   25  H1  UNL     1       3.809  -4.022  -0.037  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.060  -3.520   1.674  1.00  0.00           H  
HETATM   27  H3  UNL     1       2.446  -4.109   1.223  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.248  -1.359   2.411  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.556   0.949   1.767  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.174   4.800  -1.081  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.909   3.746  -1.042  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.456   0.164  -2.331  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.435  -1.297  -1.932  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.013  -3.401   0.658  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.789  -3.548   0.947  1.00  0.00           H  
HETATM   36  H12 UNL     1      -3.842  -2.673   2.158  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.131   0.722   1.768  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.202   2.129   1.380  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.805  -0.400  -2.174  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3   24
CONECT    3    4   28
CONECT    4    5    5   29
CONECT    5    6   23
CONECT    6    7    7   12
CONECT    7    8
CONECT    8    9    9   30
CONECT    9   10   11
CONECT   11   12   12   31
CONECT   12   13
CONECT   13   14   14   22
CONECT   14   15   32
CONECT   15   16   16   33
CONECT   16   17   21
CONECT   17   18   19   19   20
CONECT   17   20
CONECT   18   34   35   36
CONECT   21   22   22   37
CONECT   22   38
CONECT   23   24   24   39
END

HMDB0015565
     RDKit          3D
Etoricoxib
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.3188   -3.5416    0.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8995   -2.1761    0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9218   -1.1481    1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499    0.1224    1.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1329    0.4115   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7674    1.7986   -0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7156    2.7436   -0.6906 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4329    4.0243   -0.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121    4.3881   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030    6.0775   -1.4363 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1180    3.4765   -0.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4535    2.1371   -0.6634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6762    1.2425   -0.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0303    0.2921   -1.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1412   -0.5435   -1.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799   -0.3741   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2827   -1.3737    0.2093 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.8947   -2.8659    1.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3104   -0.6258    1.0202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8452   -1.7742   -1.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5480    0.5871    0.8613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4442    1.3838    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1158   -0.6056   -1.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4899   -1.8370   -0.7843 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090   -4.0224   -0.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0604   -3.5201    1.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4461   -4.1087    1.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484   -1.3586    2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5562    0.9490    1.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1736    4.8005   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9092    3.7456   -1.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4557    0.1640   -2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4351   -1.2972   -1.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0130   -3.4015    0.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7888   -3.5478    0.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8416   -2.6727    2.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1309    0.7216    1.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023    2.1289    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8045   -0.4000   -2.1744 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  0
  5  6  1  0
  6  7  2  0
  7  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  1  0
 17 19  2  0
 17 20  2  0
 16 21  1  0
 21 22  2  0
  5 23  1  0
 23 24  2  0
 24  2  1  0
 12  6  1  0
 22 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  8 30  1  0
 11 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Chloro-2-(6-methylpyridin-3-yl)-3-(4-(methylsulfonyl)phenyl)pyridine	ChEBI
5-Chloro-3-(4-methanesulfonyl-phenyl)-6'-methyl-[2,3']bipyridinyl	ChEBI
5-Chloro-6'-methyl-3-(p-(methylsulfonyl)phenyl)-2,3'-bipyridine	ChEBI
Etoricoxibum	ChEBI
L791456	ChEBI
5-Chloro-2-(6-methylpyridin-3-yl)-3-(4-(methylsulphonyl)phenyl)pyridine	Generator
5-Chloro-3-(4-methanesulphonyl-phenyl)-6'-methyl-[2,3']bipyridinyl	Generator
5-Chloro-6'-methyl-3-(p-(methylsulphonyl)phenyl)-2,3'-bipyridine	Generator
MK-663	HMDB
Arcoxia	HMDB

Chemical Formula

C₁₈H₁₅ClN₂O₂S

Average Molecular Weight

358.842

Monoisotopic Molecular Weight

358.054276131

IUPAC Name

5-chloro-3-(4-methanesulfonylphenyl)-2-(6-methylpyridin-3-yl)pyridine

Traditional Name

etoricoxib

CAS Registry Number

202409-33-4

SMILES

CC1=NC=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O

InChI Identifier

InChI=1S/C18H15ClN2O2S/c1-12-3-4-14(10-20-12)18-17(9-15(19)11-21-18)13-5-7-16(8-6-13)24(2,22)23/h3-11H,1-2H3

InChI Key

MNJVRJDLRVPLFE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Bipyridines and oligopyridines

Direct Parent

Bipyridines and oligopyridines

Alternative Parents

Substituents

Bipyridine
3-phenylpyridine
Benzenesulfonyl group
Methylpyridine
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Sulfone
Sulfonyl
Heteroaromatic compound
Azacycle
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfone (CHEBI:6339 )
organochlorine compound (CHEBI:6339 )
bipyridines (CHEBI:6339 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015565)
Membrane (HMDB: HMDB0015565)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Etoricoxib Action Pathway (PathBank: SMP0000695)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0033 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0033 g/L	ALOGPS
logP	3.7	ALOGPS
logP	2.79	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	19.69	ChemAxon
pKa (Strongest Basic)	4.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	59.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.04 m³·mol⁻¹	ChemAxon
Polarizability	36.42 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]+	185.999	30932474
DeepCCS	[M-H]-	183.641	30932474
DeepCCS	[M-2H]-	217.536	30932474
DeepCCS	[M+Na]+	192.763	30932474
AllCCS	[M+H]+	182.5	32859911
AllCCS	[M+H-H2O]+	179.3	32859911
AllCCS	[M+NH4]+	185.5	32859911
AllCCS	[M+Na]+	186.4	32859911
AllCCS	[M-H]-	180.9	32859911
AllCCS	[M+Na-2H]-	180.6	32859911
AllCCS	[M+HCOO]-	180.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Etoricoxib	CC1=NC=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O	4444.7	Standard polar	33892256
Etoricoxib	CC1=NC=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O	3145.9	Standard non polar	33892256
Etoricoxib	CC1=NC=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O	3209.4	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 - Etoricoxib GC-MS (Non-derivatized) - 70eV, Positive	splash10-00c3-1195000000-a6512b3342a7ab34b539	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoricoxib GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoricoxib 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 - Etoricoxib 10V, Positive-QTOF	splash10-0a4i-0009000000-f7a7b2b391bf2c553bee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 20V, Positive-QTOF	splash10-0a4i-0019000000-ee3806388a3685ebb2ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 40V, Positive-QTOF	splash10-014l-1093000000-f6befa9e036305228b8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 10V, Negative-QTOF	splash10-0a4i-0009000000-50b1220eaafc5cd21ae9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 20V, Negative-QTOF	splash10-0a4i-0019000000-7f9d7c868b2e84a344d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 40V, Negative-QTOF	splash10-004i-7193000000-02c1e0800c4c34dc4627	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 10V, Positive-QTOF	splash10-0a4i-0009000000-fa58affcccc87c3233cb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 20V, Positive-QTOF	splash10-0a4i-0009000000-dcccff10c50c0a3a450b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 40V, Positive-QTOF	splash10-00pr-1092000000-eccb7f42163f67d408a9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 10V, Negative-QTOF	splash10-0a4i-0009000000-6292d183612a368493ec	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 20V, Negative-QTOF	splash10-053r-9005000000-b2f21f92017e3512dfc2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 40V, Negative-QTOF	splash10-0059-9030000000-9d3d76f515503b2f8eba	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Etoricoxib Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01628	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01628	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01628

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

110209

KEGG Compound ID

C11718

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Etoricoxib

METLIN ID

Not Available

PubChem Compound

123619

PDB ID

Not Available

ChEBI ID

6339

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 Etoricoxib (HMDB0015565)

MOL for HMDB0015565 (Etoricoxib)

3D MOL for HMDB0015565 (Etoricoxib)

3D SDF for HMDB0015565 (Etoricoxib)

3D-SDF for HMDB0015565 (Etoricoxib)

PDB for HMDB0015565 (Etoricoxib)

3D PDB for HMDB0015565 (Etoricoxib)

SMILES for HMDB0015565 (Etoricoxib)

INCHI for HMDB0015565 (Etoricoxib)

Structure for HMDB0015565 (Etoricoxib)

3D Structure for HMDB0015565 (Etoricoxib)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra