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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:07:38 UTC

Update Date

2019-07-23 07:15:23 UTC

HMDB ID

HMDB0060926

Secondary Accession Numbers

HMDB60926

Metabolite Identification

Common Name

Etoricoxib 1'-N'-oxide

Description

Etoricoxib 1'-N'-oxide is a metabolite of etoricoxib. Etoricoxib (brand name NUSHIN MASCOT HEALTH SERIES Arcoxia worldwide; also Algix and Tauxib in Italy, Nucoxia in India) is a COX-2 selective inhibitor (approx. 106.0 times more selective for COX-2 inhibition over COX-1) from Merck & Co. Currently it is approved in more than 70 countries worldwide but not in the US, where the Food and Drug Administration (FDA) requires additional safety and efficacy data for etoricoxib before it will issue approval. (Wikipedia)

Structure

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

HMDB0060926
     RDKit          3D
Etoricoxib 1'-N'-oxide
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.5887   -1.7168    2.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0178   -1.0169    1.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077    0.2134    1.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879    0.8260    0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9782    0.2087   -0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4530    0.8071   -2.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2716    1.1259   -3.0950 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8380    1.6726   -4.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    1.9308   -4.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281    2.6495   -5.8254 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618    1.6106   -3.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    1.0451   -2.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446    0.6943   -0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8519   -0.6073   -0.5390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6444   -0.9601    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3783   -0.0165    1.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -0.4004    2.5836 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.0416   -0.8179    2.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7744   -1.4982    3.3834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5082    0.8236    3.4841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2814    1.2897    0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837    1.6339   -0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5959   -1.0212   -0.8778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0957   -1.6048    0.2399 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.7033   -2.8361    0.1415 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.4071   -2.8138    2.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0834   -1.3474    3.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6783   -1.4896    2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3267    0.7140    2.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252    1.7764    0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4916    1.9247   -5.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4155    1.8113   -3.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2815   -1.3627   -1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7133   -1.9828    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3811   -0.1627    1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1354   -1.8771    1.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7101   -0.6550    2.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549    2.0382    1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4007    2.6607   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6704   -1.5094   -1.8301 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 25  1  0
 24  2  1  0
 12  6  1  0
 22 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  8 31  1  0
 11 32  1  0
 14 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 21 38  1  0
 22 39  1  0
 23 40  1  0
M  CHG  2  24   1  25  -1
M  END


  Mrv0541 07091309072D          

 25 27  0  0  0  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743    2.5855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993    4.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 12  1  1  0  0  0  0
 12  3  1  0  0  0  0
 13  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14  4  1  0  0  0  0
 14 11  2  0  0  0  0
 15  9  2  0  0  0  0
 15 10  1  0  0  0  0
 16  7  2  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 18 17  2  0  0  0  0
 19 15  1  0  0  0  0
 20 10  2  0  0  0  0
 20 18  1  0  0  0  0
 21 11  1  0  0  0  0
 21 12  2  0  0  0  0
 22 21  2  0  0  0  0
 25  2  1  0  0  0  0
 25 16  1  0  0  0  0
 25 23  2  0  0  0  0
 25 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060926

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H15ClN2O3S/c1-12-3-4-14(11-21(12)22)18-17(9-15(19)10-20-18)13-5-7-16(8-6-13)25(2,23)24/h3-11H,1-2H3

> <INCHI_KEY>
KMLFAHIIJSUUPX-UHFFFAOYSA-N

> <FORMULA>
C18H15ClN2O3S

> <MOLECULAR_WEIGHT>
374.841

> <EXACT_MASS>
374.049190753

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
37.34265462581242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[5-chloro-3-(4-methanesulfonylphenyl)pyridin-2-yl]-2-methyl-1λ⁵-pyridin-1-one

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
2.119546589666667

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.693089779341896

> <JCHEM_PKA_STRONGEST_BASIC>
1.9367658169415147

> <JCHEM_POLAR_SURFACE_AREA>
72.49000000000001

> <JCHEM_REFRACTIVITY>
99.26069999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[5-chloro-3-(4-methanesulfonylphenyl)pyridin-2-yl]-2-methyl-1λ⁵-pyridin-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060926
     RDKit          3D
Etoricoxib 1'-N'-oxide
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.5887   -1.7168    2.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0178   -1.0169    1.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077    0.2134    1.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879    0.8260    0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9782    0.2087   -0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4530    0.8071   -2.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2716    1.1259   -3.0950 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8380    1.6726   -4.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    1.9308   -4.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281    2.6495   -5.8254 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618    1.6106   -3.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    1.0451   -2.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446    0.6943   -0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8519   -0.6073   -0.5390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6444   -0.9601    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3783   -0.0165    1.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -0.4004    2.5836 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.0416   -0.8179    2.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7744   -1.4982    3.3834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5082    0.8236    3.4841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2814    1.2897    0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837    1.6339   -0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5959   -1.0212   -0.8778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0957   -1.6048    0.2399 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.7033   -2.8361    0.1415 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.4071   -2.8138    2.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0834   -1.3474    3.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6783   -1.4896    2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3267    0.7140    2.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252    1.7764    0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4916    1.9247   -5.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4155    1.8113   -3.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2815   -1.3627   -1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7133   -1.9828    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3811   -0.1627    1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1354   -1.8771    1.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7101   -0.6550    2.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549    2.0382    1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4007    2.6607   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6704   -1.5094   -1.8301 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 25  1  0
 24  2  1  0
 12  6  1  0
 22 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  8 31  1  0
 11 32  1  0
 14 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 21 38  1  0
 22 39  1  0
 23 40  1  0
M  CHG  2  24   1  25  -1
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       1.334  13.090   0.000  0.00  0.00          Cl+0
HETATM   20  N   UNK     0       0.000   9.240   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       0.000   4.620   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.232   4.826   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.772   7.494   0.000  0.00  0.00           O+0
HETATM   25  S   UNK     0       8.002   6.160   0.000  0.00  0.00           S+0
CONECT    1   12                                                            
CONECT    2   25                                                            
CONECT    3    4   12                                                       
CONECT    4    3   14                                                       
CONECT    5    7   13                                                       
CONECT    6    8   13                                                       
CONECT    7    5   16                                                       
CONECT    8    6   16                                                       
CONECT    9   15   17                                                       
CONECT   10   15   20                                                       
CONECT   11   14   21                                                       
CONECT   12    1    3   21                                                  
CONECT   13    5    6   17                                                  
CONECT   14    4   11   18                                                  
CONECT   15    9   10   19                                                  
CONECT   16    7    8   25                                                  
CONECT   17    9   13   18                                                  
CONECT   18   14   17   20                                                  
CONECT   19   15                                                            
CONECT   20   10   18                                                       
CONECT   21   11   12   22                                                  
CONECT   22   21                                                            
CONECT   23   25                                                            
CONECT   24   25                                                            
CONECT   25    2   16   23   24                                             
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0060926
HETATM    1  C1  UNL     1       3.589  -1.717   2.643  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.018  -1.017   1.452  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.408   0.213   1.533  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.888   0.826   0.387  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.978   0.209  -0.840  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.453   0.807  -2.051  1.00  0.00           C  
HETATM    7  N1  UNL     1       2.272   1.126  -3.095  1.00  0.00           N  
HETATM    8  C7  UNL     1       1.838   1.673  -4.228  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.467   1.931  -4.346  1.00  0.00           C  
HETATM   10 CL1  UNL     1      -0.128   2.649  -5.825  1.00  0.00          CL  
HETATM   11  C9  UNL     1      -0.362   1.611  -3.295  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.098   1.045  -2.127  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.745   0.694  -0.990  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.852  -0.607  -0.539  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.644  -0.960   0.535  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.378  -0.016   1.219  1.00  0.00           C  
HETATM   17  S1  UNL     1      -3.395  -0.400   2.584  1.00  0.00           S  
HETATM   18  C15 UNL     1      -5.042  -0.818   2.083  1.00  0.00           C  
HETATM   19  O1  UNL     1      -2.774  -1.498   3.383  1.00  0.00           O  
HETATM   20  O2  UNL     1      -3.508   0.824   3.484  1.00  0.00           O  
HETATM   21  C16 UNL     1      -2.281   1.290   0.781  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.484   1.634  -0.297  1.00  0.00           C  
HETATM   23  C18 UNL     1       2.596  -1.021  -0.878  1.00  0.00           C  
HETATM   24  N2  UNL     1       3.096  -1.605   0.240  1.00  0.00           N1+
HETATM   25  O3  UNL     1       3.703  -2.836   0.142  1.00  0.00           O1-
HETATM   26  H1  UNL     1       3.407  -2.814   2.595  1.00  0.00           H  
HETATM   27  H2  UNL     1       3.083  -1.347   3.554  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.678  -1.490   2.764  1.00  0.00           H  
HETATM   29  H4  UNL     1       2.327   0.714   2.483  1.00  0.00           H  
HETATM   30  H5  UNL     1       1.425   1.776   0.496  1.00  0.00           H  
HETATM   31  H6  UNL     1       2.492   1.925  -5.056  1.00  0.00           H  
HETATM   32  H7  UNL     1      -1.415   1.811  -3.391  1.00  0.00           H  
HETATM   33  H8  UNL     1      -0.281  -1.363  -1.066  1.00  0.00           H  
HETATM   34  H9  UNL     1      -1.713  -1.983   0.868  1.00  0.00           H  
HETATM   35  H10 UNL     1      -5.381  -0.163   1.256  1.00  0.00           H  
HETATM   36  H11 UNL     1      -5.135  -1.877   1.768  1.00  0.00           H  
HETATM   37  H12 UNL     1      -5.710  -0.655   2.942  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.855   2.038   1.313  1.00  0.00           H  
HETATM   39  H14 UNL     1      -1.401   2.661  -0.650  1.00  0.00           H  
HETATM   40  H15 UNL     1       2.670  -1.509  -1.830  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    3   24
CONECT    3    4   29
CONECT    4    5    5   30
CONECT    5    6   23
CONECT    6    7    7   12
CONECT    7    8
CONECT    8    9    9   31
CONECT    9   10   11
CONECT   11   12   12   32
CONECT   12   13
CONECT   13   14   14   22
CONECT   14   15   33
CONECT   15   16   16   34
CONECT   16   17   21
CONECT   17   18   19   19   20
CONECT   17   20
CONECT   18   35   36   37
CONECT   21   22   22   38
CONECT   22   39
CONECT   23   24   24   40
CONECT   24   25
END

HMDB0060926
     RDKit          3D
Etoricoxib 1'-N'-oxide
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.5887   -1.7168    2.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0178   -1.0169    1.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077    0.2134    1.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879    0.8260    0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9782    0.2087   -0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4530    0.8071   -2.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2716    1.1259   -3.0950 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8380    1.6726   -4.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    1.9308   -4.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281    2.6495   -5.8254 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618    1.6106   -3.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    1.0451   -2.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446    0.6943   -0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8519   -0.6073   -0.5390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6444   -0.9601    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3783   -0.0165    1.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -0.4004    2.5836 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.0416   -0.8179    2.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7744   -1.4982    3.3834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5082    0.8236    3.4841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2814    1.2897    0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837    1.6339   -0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5959   -1.0212   -0.8778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0957   -1.6048    0.2399 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.7033   -2.8361    0.1415 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.4071   -2.8138    2.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0834   -1.3474    3.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6783   -1.4896    2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3267    0.7140    2.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252    1.7764    0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4916    1.9247   -5.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4155    1.8113   -3.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2815   -1.3627   -1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7133   -1.9828    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3811   -0.1627    1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1354   -1.8771    1.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7101   -0.6550    2.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549    2.0382    1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4007    2.6607   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6704   -1.5094   -1.8301 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 25  1  0
 24  2  1  0
 12  6  1  0
 22 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  8 31  1  0
 11 32  1  0
 14 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 21 38  1  0
 22 39  1  0
 23 40  1  0
M  CHG  2  24   1  25  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₁₅ClN₂O₃S

Average Molecular Weight

374.841

Monoisotopic Molecular Weight

374.049190753

IUPAC Name

5-[5-chloro-3-(4-methanesulfonylphenyl)pyridin-2-yl]-2-methyl-1λ⁵-pyridin-1-one

Traditional Name

5-[5-chloro-3-(4-methanesulfonylphenyl)pyridin-2-yl]-2-methyl-1λ⁵-pyridin-1-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H15ClN2O3S/c1-12-3-4-14(11-21(12)22)18-17(9-15(19)10-20-18)13-5-7-16(8-6-13)25(2,23)24/h3-11H,1-2H3

InChI Key

KMLFAHIIJSUUPX-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
Pyridinium
Heteroaromatic compound
Sulfonyl
Sulfone
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060926)
Liver (HMDB: HMDB0060926)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060926)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060926)

Cellular substructure

Cytoplasm (HMDB: HMDB0060926)
Membrane (HMDB: HMDB0060926)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0035 g/L	ALOGPS
logP	2.19	ALOGPS
logP	2.12	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	19.69	ChemAxon
pKa (Strongest Basic)	1.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	72.49 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.26 m³·mol⁻¹	ChemAxon
Polarizability	37.34 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]+	185.442	30932474
DeepCCS	[M-H]-	183.084	30932474
DeepCCS	[M-2H]-	216.27	30932474
DeepCCS	[M+Na]+	191.535	30932474
AllCCS	[M+H]+	185.1	32859911
AllCCS	[M+H-H2O]+	182.0	32859911
AllCCS	[M+NH4]+	188.0	32859911
AllCCS	[M+Na]+	188.9	32859911
AllCCS	[M-H]-	183.0	32859911
AllCCS	[M+Na-2H]-	182.7	32859911
AllCCS	[M+HCOO]-	182.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Etoricoxib 1'-N'-oxide	CC1=N(=O)C=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O	4661.3	Standard polar	33892256
Etoricoxib 1'-N'-oxide	CC1=N(=O)C=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O	3159.8	Standard non polar	33892256
Etoricoxib 1'-N'-oxide	CC1=N(=O)C=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O	3516.2	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 - Etoricoxib 1'-N'-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-052b-2196000000-28d0a8eebab555612422	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoricoxib 1'-N'-oxide 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 1'-N'-oxide 10V, Positive-QTOF	splash10-004i-0009000000-ea86b98358ff2807256a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 1'-N'-oxide 20V, Positive-QTOF	splash10-004j-0159000000-5676d1ba524f39f83c28	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 1'-N'-oxide 40V, Positive-QTOF	splash10-0h00-3291000000-e81800c3c5e625517551	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 1'-N'-oxide 10V, Negative-QTOF	splash10-00di-0009000000-4f29b67d80e27eaafe32	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 1'-N'-oxide 20V, Negative-QTOF	splash10-00di-0119000000-2b0ffae7046472470d00	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoricoxib 1'-N'-oxide 40V, Negative-QTOF	splash10-004j-9071000000-93da31a02baa761ef613	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44266508

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Etoricoxib 1'-N'-oxide (HMDB0060926)

MOL for HMDB0060926 (Etoricoxib 1'-N'-oxide)

3D MOL for HMDB0060926 (Etoricoxib 1'-N'-oxide)

3D SDF for HMDB0060926 (Etoricoxib 1'-N'-oxide)

3D-SDF for HMDB0060926 (Etoricoxib 1'-N'-oxide)

PDB for HMDB0060926 (Etoricoxib 1'-N'-oxide)

3D PDB for HMDB0060926 (Etoricoxib 1'-N'-oxide)

SMILES for HMDB0060926 (Etoricoxib 1'-N'-oxide)

INCHI for HMDB0060926 (Etoricoxib 1'-N'-oxide)

Structure for HMDB0060926 (Etoricoxib 1'-N'-oxide)

3D Structure for HMDB0060926 (Etoricoxib 1'-N'-oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra