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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:44 UTC

Update Date

2020-02-26 21:39:19 UTC

HMDB ID

HMDB0013988

Secondary Accession Numbers

HMDB13988

Metabolite Identification

Common Name

N-Deschlorobenzoyl indomethacin

Description

N-Deschlorobenzoyl indomethacin, also known as DBI or 5-methoxy-methylindoleacetic acid, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. Based on a literature review a significant number of articles have been published on N-Deschlorobenzoyl indomethacin.

Structure

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

HMDB0013988
     RDKit          3D
N-Deschlorobenzoyl indomethacin
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.7192   -0.6843   -0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3863   -1.1590   -0.8929 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358   -0.2943   -0.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6173    1.0427   -0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5938    1.8949   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2834    1.4621   -0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9014    2.0550    0.2233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8979    1.1318    0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3236    1.4628    0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3399   -0.0858   -0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1313   -1.3334   -0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5553   -1.9170    0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2480   -1.3542    1.9516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859   -3.0782    0.9136 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    0.1306   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0291   -0.7358   -0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9221    0.0653   -1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3651   -1.5998   -1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9741   -0.2344    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6433    1.3950   -0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7374    2.9565    0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0111    3.0648    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6444    2.1402   -0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4780    1.9673    1.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9276    0.5358    0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -2.0437   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0824   -1.0144   -0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9481   -3.9975    0.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8059   -1.7731   -0.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 10 15  1  0
 15 16  2  0
 16  3  1  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 16 29  1  0
M  END


  Mrv0541 11291309302D          

 16 17  0  0  0  0            999 V2000
    6.9595   -3.6368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8453   -5.6582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7815   -4.7039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8836   -2.1479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8836   -3.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1030   -3.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1030   -2.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3651   -2.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1397   -4.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3885   -3.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3885   -1.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1900   -2.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6740   -3.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6740   -2.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5887   -4.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2449   -3.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  1 16  1  0  0  0  0
  2 15  1  0  0  0  0
  3 15  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6  7  2  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 15  1  0  0  0  0
 10 13  2  0  0  0  0
 11 14  2  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013988

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(NC(C)=C2CC(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H13NO3/c1-7-9(6-12(14)15)10-5-8(16-2)3-4-11(10)13-7/h3-5,13H,6H2,1-2H3,(H,14,15)

> <INCHI_KEY>
TXWGINUZLBAKDF-UHFFFAOYSA-N

> <FORMULA>
C12H13NO3

> <MOLECULAR_WEIGHT>
219.2365

> <EXACT_MASS>
219.089543287

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.104359095456687

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(5-methoxy-2-methyl-1H-indol-3-yl)acetic acid

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
1.7516461556666658

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.7105990393807

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.382389760819119

> <JCHEM_PKA_STRONGEST_BASIC>
-4.830633599929029

> <JCHEM_POLAR_SURFACE_AREA>
62.32

> <JCHEM_REFRACTIVITY>
60.06500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5-methoxy-2-methyl-1H-indol-3-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013988
     RDKit          3D
N-Deschlorobenzoyl indomethacin
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.7192   -0.6843   -0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3863   -1.1590   -0.8929 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358   -0.2943   -0.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6173    1.0427   -0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5938    1.8949   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2834    1.4621   -0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9014    2.0550    0.2233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8979    1.1318    0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3236    1.4628    0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3399   -0.0858   -0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1313   -1.3334   -0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5553   -1.9170    0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2480   -1.3542    1.9516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859   -3.0782    0.9136 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    0.1306   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0291   -0.7358   -0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9221    0.0653   -1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3651   -1.5998   -1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9741   -0.2344    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6433    1.3950   -0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7374    2.9565    0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0111    3.0648    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6444    2.1402   -0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4780    1.9673    1.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9276    0.5358    0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -2.0437   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0824   -1.0144   -0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9481   -3.9975    0.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8059   -1.7731   -0.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 10 15  1  0
 15 16  2  0
 16  3  1  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 29-NOV-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-NOV-13         0                                  
HETATM    1  O   UNK     0      12.991  -6.789   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      18.378 -10.562   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      16.392  -8.781   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      18.449  -4.009   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      18.449  -6.488   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.992  -6.019   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.992  -4.479   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.348  -5.249   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.927  -7.952   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.659  -6.789   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.659  -3.709   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.888  -5.249   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.325  -6.019   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.325  -4.479   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.899  -9.098   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.657  -6.019   0.000  0.00  0.00           C+0
CONECT    1   13   16                                                       
CONECT    2   15                                                            
CONECT    3   15                                                            
CONECT    4    7    8                                                       
CONECT    5    6    8    9                                                  
CONECT    6    5    7   10                                                  
CONECT    7    4    6   11                                                  
CONECT    8    4    5   12                                                  
CONECT    9    5   15                                                       
CONECT   10    6   13                                                       
CONECT   11    7   14                                                       
CONECT   12    8                                                            
CONECT   13    1   10   14                                                  
CONECT   14   11   13                                                       
CONECT   15    2    3    9                                                  
CONECT   16    1                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0013988
HETATM    1  C1  UNL     1       4.719  -0.684  -0.910  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.386  -1.159  -0.893  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.336  -0.294  -0.604  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.617   1.043  -0.338  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.594   1.895  -0.054  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.283   1.462  -0.024  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.901   2.055   0.223  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.898   1.132   0.119  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.324   1.463   0.331  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.340  -0.086  -0.203  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.131  -1.333  -0.387  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.555  -1.917   0.884  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.248  -1.354   1.952  1.00  0.00           O  
HETATM   14  O3  UNL     1      -3.286  -3.078   0.914  1.00  0.00           O  
HETATM   15  C11 UNL     1       0.012   0.131  -0.289  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.029  -0.736  -0.576  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.922   0.065  -1.693  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.365  -1.600  -1.017  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.974  -0.234   0.095  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.643   1.395  -0.358  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.737   2.957   0.165  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.011   3.065   0.456  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.644   2.140  -0.486  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.478   1.967   1.322  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.928   0.536   0.384  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.650  -2.044  -1.091  1.00  0.00           H  
HETATM   27  H11 UNL     1      -3.082  -1.014  -0.912  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.948  -3.998   0.628  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.806  -1.773  -0.782  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4   16
CONECT    4    5   20
CONECT    5    6    6   21
CONECT    6    7   15
CONECT    7    8   22
CONECT    8    9   10   10
CONECT    9   23   24   25
CONECT   10   11   15
CONECT   11   12   26   27
CONECT   12   13   13   14
CONECT   14   28
CONECT   15   16   16
CONECT   16   29
END

HMDB0013988
     RDKit          3D
N-Deschlorobenzoyl indomethacin
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.7192   -0.6843   -0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3863   -1.1590   -0.8929 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358   -0.2943   -0.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6173    1.0427   -0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5938    1.8949   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2834    1.4621   -0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9014    2.0550    0.2233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8979    1.1318    0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3236    1.4628    0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3399   -0.0858   -0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1313   -1.3334   -0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5553   -1.9170    0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2480   -1.3542    1.9516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859   -3.0782    0.9136 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    0.1306   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0291   -0.7358   -0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9221    0.0653   -1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3651   -1.5998   -1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9741   -0.2344    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6433    1.3950   -0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7374    2.9565    0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0111    3.0648    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6444    2.1402   -0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4780    1.9673    1.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9276    0.5358    0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -2.0437   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0824   -1.0144   -0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9481   -3.9975    0.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8059   -1.7731   -0.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 10 15  1  0
 15 16  2  0
 16  3  1  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 16 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Des-4-chlorobenzoyl)indomethacin	HMDB
DBI	HMDB
Deschlorobenzoylindomethacin	HMDB
5-Methoxy-methylindoleacetic acid	HMDB
2-(5-Methoxy-2-methyl-1H-indol-3-yl)acetate	HMDB
5-Methoxy-2-methyl-3-indoleacetic acid	HMDB
5-Methoxy-2-methyl-3-indoleacetate	HMDB

Chemical Formula

C₁₂H₁₃NO₃

Average Molecular Weight

219.2365

Monoisotopic Molecular Weight

219.089543287

IUPAC Name

2-(5-methoxy-2-methyl-1H-indol-3-yl)acetic acid

Traditional Name

(5-methoxy-2-methyl-1H-indol-3-yl)acetic acid

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(NC(C)=C2CC(O)=O)C=C1

InChI Identifier

InChI=1S/C12H13NO3/c1-7-9(6-12(14)15)10-5-8(16-2)3-4-11(10)13-7/h3-5,13H,6H2,1-2H3,(H,14,15)

InChI Key

TXWGINUZLBAKDF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indole-3-acetic acid derivatives

Alternative Parents

Substituents

Indole-3-acetic acid derivative
3-alkylindole
Indole
Anisole
Alkyl aryl ether
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013988)

Organ

Liver (HMDB: HMDB0013988)
Kidney (HMDB: HMDB0013988)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Source

Endogenous

Endogenous (HMDB: HMDB0013988)

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	0.37 g/L	ALOGPS
logP	1.93	ALOGPS
logP	1.75	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.38	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.06 m³·mol⁻¹	ChemAxon
Polarizability	23.1 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	151.525	31661259
DarkChem	[M-H]-	152.301	31661259
DeepCCS	[M+H]+	150.262	30932474
DeepCCS	[M-H]-	147.904	30932474
DeepCCS	[M-2H]-	180.915	30932474
DeepCCS	[M+Na]+	156.356	30932474
AllCCS	[M+H]+	148.1	32859911
AllCCS	[M+H-H2O]+	144.1	32859911
AllCCS	[M+NH4]+	151.9	32859911
AllCCS	[M+Na]+	153.0	32859911
AllCCS	[M-H]-	150.7	32859911
AllCCS	[M+Na-2H]-	150.7	32859911
AllCCS	[M+HCOO]-	150.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.99 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8929 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.12 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1776.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	325.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	129.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	483.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	471.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	94.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	810.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	424.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1273.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	345.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	340.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	430.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	268.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	187.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Deschlorobenzoyl indomethacin	COC1=CC2=C(NC(C)=C2CC(O)=O)C=C1	3599.2	Standard polar	33892256
N-Deschlorobenzoyl indomethacin	COC1=CC2=C(NC(C)=C2CC(O)=O)C=C1	2059.4	Standard non polar	33892256
N-Deschlorobenzoyl indomethacin	COC1=CC2=C(NC(C)=C2CC(O)=O)C=C1	2250.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Deschlorobenzoyl indomethacin,1TMS,isomer #1	COC1=CC=C2[NH]C(C)=C(CC(=O)O[Si](C)(C)C)C2=C1	2153.1	Semi standard non polar	33892256
N-Deschlorobenzoyl indomethacin,1TMS,isomer #2	COC1=CC=C2C(=C1)C(CC(=O)O)=C(C)N2[Si](C)(C)C	2298.7	Semi standard non polar	33892256
N-Deschlorobenzoyl indomethacin,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C)=C(C)N2[Si](C)(C)C	2264.7	Semi standard non polar	33892256
N-Deschlorobenzoyl indomethacin,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C)=C(C)N2[Si](C)(C)C	2160.7	Standard non polar	33892256
N-Deschlorobenzoyl indomethacin,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C)=C(C)N2[Si](C)(C)C	2437.9	Standard polar	33892256
N-Deschlorobenzoyl indomethacin,1TBDMS,isomer #1	COC1=CC=C2[NH]C(C)=C(CC(=O)O[Si](C)(C)C(C)(C)C)C2=C1	2403.3	Semi standard non polar	33892256
N-Deschlorobenzoyl indomethacin,1TBDMS,isomer #2	COC1=CC=C2C(=C1)C(CC(=O)O)=C(C)N2[Si](C)(C)C(C)(C)C	2469.2	Semi standard non polar	33892256
N-Deschlorobenzoyl indomethacin,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C(C)N2[Si](C)(C)C(C)(C)C	2653.1	Semi standard non polar	33892256
N-Deschlorobenzoyl indomethacin,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C(C)N2[Si](C)(C)C(C)(C)C	2595.6	Standard non polar	33892256
N-Deschlorobenzoyl indomethacin,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C(C)N2[Si](C)(C)C(C)(C)C	2646.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Deschlorobenzoyl indomethacin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g6r-1930000000-c902052d62113a2bd761	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Deschlorobenzoyl indomethacin GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9450000000-20eed150b22817573dc8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Deschlorobenzoyl indomethacin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Deschlorobenzoyl indomethacin 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 - N-Deschlorobenzoyl indomethacin 10V, Positive-QTOF	splash10-0fk9-0490000000-1b6deba39ddb200d9630	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Deschlorobenzoyl indomethacin 20V, Positive-QTOF	splash10-00di-0920000000-1bd60de0b34548e151ba	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Deschlorobenzoyl indomethacin 40V, Positive-QTOF	splash10-06yo-0900000000-cd0848a732e4440898d7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Deschlorobenzoyl indomethacin 10V, Negative-QTOF	splash10-014i-0590000000-adb7e0d176d49d9314ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Deschlorobenzoyl indomethacin 20V, Negative-QTOF	splash10-01b9-0970000000-1a706f68bf9e2ef7d2af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Deschlorobenzoyl indomethacin 40V, Negative-QTOF	splash10-0pb9-1910000000-96d4d8083944929c5985	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Deschlorobenzoyl indomethacin 10V, Positive-QTOF	splash10-00di-0920000000-a734885077ff73c55646	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Deschlorobenzoyl indomethacin 20V, Positive-QTOF	splash10-00di-0900000000-925c26cea4d102697a13	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Deschlorobenzoyl indomethacin 40V, Positive-QTOF	splash10-0006-0900000000-ee0e85ff60928e828063	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Deschlorobenzoyl indomethacin 10V, Negative-QTOF	splash10-00di-0910000000-3e0cbfd5ef74b48932a1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Deschlorobenzoyl indomethacin 20V, Negative-QTOF	splash10-0ab9-0900000000-a7fa463a4f3dad8fbca5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Deschlorobenzoyl indomethacin 40V, Negative-QTOF	splash10-0a4i-0900000000-5cdf26ac94b470037139	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

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	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	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

68635

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76151

PDB ID

Not Available

ChEBI ID

235459

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 N-Deschlorobenzoyl indomethacin (HMDB0013988)

MOL for HMDB0013988 (N-Deschlorobenzoyl indomethacin)

3D MOL for HMDB0013988 (N-Deschlorobenzoyl indomethacin)

3D SDF for HMDB0013988 (N-Deschlorobenzoyl indomethacin)

3D-SDF for HMDB0013988 (N-Deschlorobenzoyl indomethacin)

PDB for HMDB0013988 (N-Deschlorobenzoyl indomethacin)

3D PDB for HMDB0013988 (N-Deschlorobenzoyl indomethacin)

SMILES for HMDB0013988 (N-Deschlorobenzoyl indomethacin)

INCHI for HMDB0013988 (N-Deschlorobenzoyl indomethacin)

Structure for HMDB0013988 (N-Deschlorobenzoyl indomethacin)

3D Structure for HMDB0013988 (N-Deschlorobenzoyl indomethacin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra