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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8)transporters (1) Show 9 proteins XML

enzymes (8)transporters (1) Show 9 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:43 UTC

HMDB ID

HMDB0014743

Secondary Accession Numbers

HMDB14743

Metabolite Identification

Common Name

Sulindac

Description

Sulindac is a nonsteroidal anti-inflammatory agent (NSAIA) of the arylalkanoic acid class that is marketed in the U.S. by Merck as Clinoril. Like other NSAIAs, it may be used in the treatment of acute or chronic inflammatory conditions. Sulindac is a prodrug, derived from sulfinylindene, that is converted in vivo to an active sulfide compound by liver enzymes. The sulfide metabolite then undergoes enterohepatic circulation; it is excreted in the bile and then reabsorbed from the intestine. This is thought to help maintain constant blood levels with reduced gastrointestinal side effects. Some studies have shown sulindac to be relatively less irritating to the stomach than other NSAIA's except for drugs of the cyclooxygenase-2 (COX-2) inhibitor class. The exact mechanism of its NSAIA properties is unknown, but it is thought to act on enzymes COX-1 and COX-2, inhibiting prostaglandin synthesis.

Structure

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

HMDB0014743
     RDKit          3D
Sulindac
 42 44  0  0  0  0  0  0  0  0999 V2000
    2.4392   -2.8831    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689   -1.4523   -0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -0.5279   -0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -0.8315   -0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2714   -0.2445    0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8660    0.8464    0.7820 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2835   -0.9291    2.0420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094    0.7808   -0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0386    2.0422   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2082    3.1429   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393    4.3857   -0.7787 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552    2.9520   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732    1.6964   -0.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1215    0.6212   -0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8525   -0.7769   -0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2806   -1.3905    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5470   -0.7299    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1646   -0.3281   -0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4135    0.2926   -0.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0322    0.5069    0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6296    1.2953    0.3697 S   0  0  0  0  0  4  0  0  0  0  0  0
   -6.8944    0.0312    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7270    1.9473    1.7546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4165    0.1053    1.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1772   -0.5089    1.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1089   -3.2847   -0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -3.0397    1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5188   -3.4845    0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462   -1.9304   -0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9313   -0.4024   -1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1220   -1.9410    2.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0934    2.2384   -0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232    3.8219   -0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7765    1.6725   -0.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239   -2.4997    0.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7113   -0.4757   -1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    0.6071   -1.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6736    0.2790   -0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3650   -0.1236    1.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4212   -0.9582   -0.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9368    0.2916    2.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214   -0.8139    2.3010 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  1  0
  5  6  2  0
  5  7  1  0
  3  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 20 24  1  0
 24 25  2  0
 15  2  1  0
 25 17  1  0
 14  8  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 22 38  1  0
 22 39  1  0
 22 40  1  0
 24 41  1  0
 25 42  1  0
M  END


  Mrv0541 04191212132D          

 25 27  0  0  0  0            999 V2000
   10.8582   -5.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5256   -4.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2707   -4.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4457   -4.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1908   -4.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8937   -3.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0867   -3.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8317   -4.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3838   -4.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8582   -6.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1437   -6.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4292   -6.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7148   -6.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7148   -7.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4292   -7.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1437   -7.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0003   -7.7630    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0003   -8.5880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2858   -7.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8540   -3.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6509   -3.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2343   -3.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9370   -4.4274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5033   -2.9935    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.3225   -5.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  1  5  1  0  0  0  0
  6  4  2  0  0  0  0
  5  4  1  0  0  0  0
  9  5  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  1 10  2  0  0  0  0
 10 11  1  0  0  0  0
 16 11  2  0  0  0  0
 12 11  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
  7 24  1  0  0  0  0
  2 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014743

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(C=C1)S(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H17FO3S/c1-12-17(9-13-3-6-15(7-4-13)25(2)24)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-

> <INCHI_KEY>
MLKXDPUZXIRXEP-MFOYZWKCSA-N

> <FORMULA>
C20H17FO3S

> <MOLECULAR_WEIGHT>
356.411

> <EXACT_MASS>
356.088243305

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.20104119112119

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1Z)-5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1H-inden-3-yl]acetic acid

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
2.9261546376666665

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.371149972919564

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.090206179286022

> <JCHEM_PKA_STRONGEST_BASIC>
-6.655325429806263

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
99.5588

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulindac

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014743
     RDKit          3D
Sulindac
 42 44  0  0  0  0  0  0  0  0999 V2000
    2.4392   -2.8831    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689   -1.4523   -0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -0.5279   -0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -0.8315   -0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2714   -0.2445    0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8660    0.8464    0.7820 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2835   -0.9291    2.0420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094    0.7808   -0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0386    2.0422   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2082    3.1429   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393    4.3857   -0.7787 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552    2.9520   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732    1.6964   -0.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1215    0.6212   -0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8525   -0.7769   -0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2806   -1.3905    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5470   -0.7299    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1646   -0.3281   -0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4135    0.2926   -0.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0322    0.5069    0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6296    1.2953    0.3697 S   0  0  0  0  0  4  0  0  0  0  0  0
   -6.8944    0.0312    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7270    1.9473    1.7546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4165    0.1053    1.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1772   -0.5089    1.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1089   -3.2847   -0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -3.0397    1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5188   -3.4845    0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462   -1.9304   -0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9313   -0.4024   -1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1220   -1.9410    2.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0934    2.2384   -0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232    3.8219   -0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7765    1.6725   -0.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239   -2.4997    0.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7113   -0.4757   -1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    0.6071   -1.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6736    0.2790   -0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3650   -0.1236    1.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4212   -0.9582   -0.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9368    0.2916    2.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214   -0.8139    2.3010 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  1  0
  5  6  2  0
  5  7  1  0
  3  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 20 24  1  0
 24 25  2  0
 15  2  1  0
 25 17  1  0
 14  8  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 22 38  1  0
 22 39  1  0
 22 40  1  0
 24 41  1  0
 25 42  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      20.269  -9.871   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.514  -8.966   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.039  -7.501   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.499  -7.501   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.023  -8.966   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.468  -6.357   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.962  -6.677   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.486  -8.141   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.516  -9.286   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.269 -11.411   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.935 -12.181   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.601 -11.411   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.268 -12.181   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.268 -13.721   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.601 -14.491   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.935 -13.721   0.000  0.00  0.00           C+0
HETATM   17  S   UNK     0      14.934 -14.491   0.000  0.00  0.00           S+0
HETATM   18  O   UNK     0      14.934 -16.031   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      13.600 -13.721   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.127  -6.412   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.615  -6.811   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      24.704  -5.722   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      24.149  -8.264   0.000  0.00  0.00           O+0
HETATM   24  F   UNK     0      15.873  -5.588   0.000  0.00  0.00           F+0
HETATM   25  C   UNK     0      23.002  -9.364   0.000  0.00  0.00           C+0
CONECT    1    2    5   10                                                  
CONECT    2    1    3   25                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    6    5                                                  
CONECT    5    1    4    9                                                  
CONECT    6    4    7                                                       
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    5    8                                                       
CONECT   10    1   11                                                       
CONECT   11   10   16   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   11   15                                                       
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    3   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    7                                                            
CONECT   25    2                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0014743
HETATM    1  C1  UNL     1       2.439  -2.883   0.076  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.169  -1.452  -0.067  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.117  -0.528  -0.247  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.572  -0.831  -0.326  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.271  -0.245   0.825  1.00  0.00           C  
HETATM    6  O1  UNL     1       5.866   0.846   0.782  1.00  0.00           O  
HETATM    7  O2  UNL     1       5.283  -0.929   2.042  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.509   0.781  -0.351  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.039   2.042  -0.536  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.208   3.143  -0.591  1.00  0.00           C  
HETATM   11  F1  UNL     1       2.739   4.386  -0.779  1.00  0.00           F  
HETATM   12  C9  UNL     1       0.855   2.952  -0.457  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.273   1.696  -0.269  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.122   0.621  -0.222  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.853  -0.777  -0.041  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.281  -1.391   0.143  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.547  -0.730   0.157  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.165  -0.328  -0.995  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.414   0.293  -0.934  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.032   0.507   0.274  1.00  0.00           C  
HETATM   21  S1  UNL     1      -5.630   1.295   0.370  1.00  0.00           S  
HETATM   22  C18 UNL     1      -6.894   0.031   0.226  1.00  0.00           C  
HETATM   23  O3  UNL     1      -5.727   1.947   1.755  1.00  0.00           O  
HETATM   24  C19 UNL     1      -3.417   0.105   1.447  1.00  0.00           C  
HETATM   25  C20 UNL     1      -2.177  -0.509   1.359  1.00  0.00           C  
HETATM   26  H1  UNL     1       3.109  -3.285  -0.718  1.00  0.00           H  
HETATM   27  H2  UNL     1       2.944  -3.040   1.073  1.00  0.00           H  
HETATM   28  H3  UNL     1       1.519  -3.485   0.061  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.746  -1.930  -0.301  1.00  0.00           H  
HETATM   30  H5  UNL     1       4.931  -0.402  -1.289  1.00  0.00           H  
HETATM   31  H6  UNL     1       5.122  -1.941   2.018  1.00  0.00           H  
HETATM   32  H7  UNL     1       4.093   2.238  -0.656  1.00  0.00           H  
HETATM   33  H8  UNL     1       0.223   3.822  -0.503  1.00  0.00           H  
HETATM   34  H9  UNL     1      -0.777   1.672  -0.151  1.00  0.00           H  
HETATM   35  H10 UNL     1      -0.224  -2.500   0.293  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.711  -0.476  -1.951  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.890   0.607  -1.870  1.00  0.00           H  
HETATM   38  H13 UNL     1      -7.674   0.279  -0.525  1.00  0.00           H  
HETATM   39  H14 UNL     1      -7.365  -0.124   1.213  1.00  0.00           H  
HETATM   40  H15 UNL     1      -6.421  -0.958  -0.048  1.00  0.00           H  
HETATM   41  H16 UNL     1      -3.937   0.292   2.378  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.721  -0.814   2.301  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    3   15
CONECT    3    4    8
CONECT    4    5   29   30
CONECT    5    6    6    7
CONECT    7   31
CONECT    8    9    9   14
CONECT    9   10   32
CONECT   10   11   12   12
CONECT   12   13   33
CONECT   13   14   14   34
CONECT   14   15
CONECT   15   16   16
CONECT   16   17   35
CONECT   17   18   18   25
CONECT   18   19   36
CONECT   19   20   20   37
CONECT   20   21   24
CONECT   21   22   23   23
CONECT   22   38   39   40
CONECT   24   25   25   41
CONECT   25   42
END

HMDB0014743
     RDKit          3D
Sulindac
 42 44  0  0  0  0  0  0  0  0999 V2000
    2.4392   -2.8831    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689   -1.4523   -0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -0.5279   -0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -0.8315   -0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2714   -0.2445    0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8660    0.8464    0.7820 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2835   -0.9291    2.0420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094    0.7808   -0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0386    2.0422   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2082    3.1429   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393    4.3857   -0.7787 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552    2.9520   -0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732    1.6964   -0.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1215    0.6212   -0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8525   -0.7769   -0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2806   -1.3905    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5470   -0.7299    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1646   -0.3281   -0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4135    0.2926   -0.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0322    0.5069    0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6296    1.2953    0.3697 S   0  0  0  0  0  4  0  0  0  0  0  0
   -6.8944    0.0312    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7270    1.9473    1.7546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4165    0.1053    1.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1772   -0.5089    1.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1089   -3.2847   -0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -3.0397    1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5188   -3.4845    0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462   -1.9304   -0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9313   -0.4024   -1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1220   -1.9410    2.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0934    2.2384   -0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232    3.8219   -0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7765    1.6725   -0.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239   -2.4997    0.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7113   -0.4757   -1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    0.6071   -1.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6736    0.2790   -0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3650   -0.1236    1.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4212   -0.9582   -0.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9368    0.2916    2.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214   -0.8139    2.3010 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  1  0
  5  6  2  0
  5  7  1  0
  3  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 20 24  1  0
 24 25  2  0
 15  2  1  0
 25 17  1  0
 14  8  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 22 38  1  0
 22 39  1  0
 22 40  1  0
 24 41  1  0
 25 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Z)-5-Fluoro-2-methyl-1-((p-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid	ChEBI
cis-5-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid	ChEBI
cis-5-Fluoro-2-methyl-1-((p-methylsulfinyl)benzylidene)indene-3-acetic acid	ChEBI
Clinoril	ChEBI
Sulindaco	ChEBI
Sulindacum	ChEBI
(Z)-5-Fluoro-2-methyl-1-((p-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetate	Generator
(Z)-5-Fluoro-2-methyl-1-((p-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetate	Generator
(Z)-5-Fluoro-2-methyl-1-((p-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetic acid	Generator
cis-5-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetate	Generator
cis-5-Fluoro-2-methyl-1-((4-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetate	Generator
cis-5-Fluoro-2-methyl-1-((4-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetic acid	Generator
cis-5-Fluoro-2-methyl-1-((p-methylsulfinyl)benzylidene)indene-3-acetate	Generator
cis-5-Fluoro-2-methyl-1-((p-methylsulphinyl)benzylidene)indene-3-acetate	Generator
cis-5-Fluoro-2-methyl-1-((p-methylsulphinyl)benzylidene)indene-3-acetic acid	Generator
Aclin	HMDB
Arthrobid	HMDB
Cahill may roberts brand OF sulindac	HMDB
Chemia brand OF sulindac	HMDB
Copal	HMDB
Novo-sundac	HMDB
Nu pharm brand OF sulindac	HMDB
Sulindal	HMDB
Apo-sulin	HMDB
Kendrick brand OF sulindac	HMDB
Merck sharp and dohme brand OF sulindac	HMDB
Apotex brand OF sulindac	HMDB
Arthrocine	HMDB
Chibret	HMDB
Kenalin	HMDB
Klinoril	HMDB
Novo sundac	HMDB
Novopharm brand OF sulindac	HMDB
Alphapharm brand OF sulindac	HMDB
Apo sulin	HMDB
Merck brand OF sulindac	HMDB
Nu sulindac	HMDB
Nu-pharm brand OF sulindac	HMDB
Nu-sulindac	HMDB

Chemical Formula

C₂₀H₁₇FO₃S

Average Molecular Weight

356.411

Monoisotopic Molecular Weight

356.088243305

IUPAC Name

2-[(1Z)-5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1H-inden-3-yl]acetic acid

Traditional Name

sulindac

CAS Registry Number

38194-50-2

SMILES

CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(C=C1)S(C)=O

InChI Identifier

InChI=1S/C20H17FO3S/c1-12-17(9-13-3-6-15(7-4-13)25(2)24)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-

InChI Key

MLKXDPUZXIRXEP-MFOYZWKCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indenes and isoindenes. Indenes and isoindenes are compounds containing an indene moiety(which consists of a cyclopentadiene fused to a benzene ring), or a isoindene moiety (which consists of a cyclopentadiene fused to cyclohexadiene ring).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Indenes and isoindenes

Sub Class

Not Available

Direct Parent

Indenes and isoindenes

Alternative Parents

Substituents

Phenyl sulfoxide
Indene
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Sulfoxide
Sulfinyl compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organohalogen compound
Organofluoride
Organooxygen compound
Organosulfur compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:9352 )
monocarboxylic acid (CHEBI:9352 )
sulfoxide (CHEBI:9352 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Sulindac Action Pathway (PathBank: SMP0000094)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	183 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.025 g/L	Not Available
LogP	3.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	192.6	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	2.96	ALOGPS
logP	2.93	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.56 m³·mol⁻¹	ChemAxon
Polarizability	37.2 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]+	179.541	30932474
DeepCCS	[M-H]-	177.184	30932474
DeepCCS	[M-2H]-	211.276	30932474
DeepCCS	[M+Na]+	186.503	30932474
AllCCS	[M+H]+	184.1	32859911
AllCCS	[M+H-H2O]+	181.0	32859911
AllCCS	[M+NH4]+	186.9	32859911
AllCCS	[M+Na]+	187.8	32859911
AllCCS	[M-H]-	183.5	32859911
AllCCS	[M+Na-2H]-	183.1	32859911
AllCCS	[M+HCOO]-	182.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sulindac	CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(C=C1)S(C)=O	5165.5	Standard polar	33892256
Sulindac	CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(C=C1)S(C)=O	2895.9	Standard non polar	33892256
Sulindac	CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(C=C1)S(C)=O	3195.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sulindac,1TMS,isomer #1	CC1=C(CC(=O)O[Si](C)(C)C)C2=CC(F)=CC=C2/C1=C\C1=CC=C(S(C)=O)C=C1	3131.3	Semi standard non polar	33892256
Sulindac,1TBDMS,isomer #1	CC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C2=CC(F)=CC=C2/C1=C\C1=CC=C(S(C)=O)C=C1	3365.6	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 - Sulindac GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-2049000000-ee0d75c6250b16c1d750	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulindac GC-MS (1 TMS) - 70eV, Positive	splash10-03ki-9026500000-09ffdf8287c75b771d27	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulindac 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulindac LC-ESI-qTof , Positive-QTOF	splash10-001j-1290000000-33b23a68145a3ef2000c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulindac LC-ESI-QQ , positive-QTOF	splash10-0a4i-0019000000-fec3a7dbf1ba6b64f03e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulindac LC-ESI-QQ , positive-QTOF	splash10-0a4i-0019000000-6a9b19701aa1af58166d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulindac LC-ESI-QQ , positive-QTOF	splash10-001l-0095000000-1aef30e1f36f3fcc9ea2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulindac LC-ESI-QQ , positive-QTOF	splash10-001j-0090000000-4f30705a14fab7bb25e0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulindac LC-ESI-QQ , positive-QTOF	splash10-001i-0090000000-8bf873219e6e4353be1e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulindac LC-ESI-IT , positive-QTOF	splash10-000y-0095000000-0a507959838acf3f73cb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulindac , positive-QTOF	splash10-0a4i-0059000000-3ad0cecc4eb73cce225e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulindac , positive-QTOF	splash10-0a4i-0069000000-be643d55172bd2292511	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulindac , positive-QTOF	splash10-001j-1290000000-33b23a68145a3ef2000c	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac 10V, Positive-QTOF	splash10-0a4r-0009000000-aa01817d10171df35e25	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac 20V, Positive-QTOF	splash10-03di-0229000000-cf8ae62ab9c9a2b04d59	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac 40V, Positive-QTOF	splash10-0002-3591000000-a4e5854feef934299dce	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac 10V, Negative-QTOF	splash10-0bt9-2029000000-1008aba76fe664bb42e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac 20V, Negative-QTOF	splash10-08fr-4059000000-059edf52b4661bfc81ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac 40V, Negative-QTOF	splash10-03dl-9031000000-f66b9288554dc37968c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac 10V, Positive-QTOF	splash10-0a4r-0009000000-72d296d26dcda3b7ae09	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac 20V, Positive-QTOF	splash10-0bti-0009000000-892fc6f6c746c9f48f15	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac 40V, Positive-QTOF	splash10-0005-0191000000-4bbbf45eea7d16fde5bf	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac 10V, Negative-QTOF	splash10-08fr-0009000000-f37cc66528ef3b96ffcb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac 20V, Negative-QTOF	splash10-08fr-2009000000-e7c5432f2cda09c51a8e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac 40V, Negative-QTOF	splash10-0292-4093000000-259994ac6b903c437345	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Sulindac 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 DB00605	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00605	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00605

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1265915

KEGG Compound ID

C01531

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulindac

METLIN ID

Not Available

PubChem Compound

1548887

PDB ID

Not Available

ChEBI ID

9352

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)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. Aldose reductase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:: AKR1B1
Uniprot ID:: P15121
Molecular weight:: 35853.125

References

Sharma YR, Vajpayee RB, Bhatnagar R, Mohan M, Azad RV, Kumar M, Nath R: Topical sulindac therapy in diabetic senile cataracts: cataract-IV. Indian J Ophthalmol. 1989 Jul-Sep;37(3):127-33. [PubMed:2632448 ]
Crabbe MJ, Freeman G, Halder AB, Bron AJ: The inhibition of bovine lens aldose reductase by Clinoril, its absorption into the human red cell and its effect on human red cell aldose reductase activity. Ophthalmic Res. 1985;17(2):85-9. [PubMed:3920599 ]
Chaudhry PS, Cabrera J, Juliani HR, Varma SD: Inhibition of human lens aldose reductase by flavonoids, sulindac and indomethacin. Biochem Pharmacol. 1983 Jul 1;32(13):1995-8. [PubMed:6409111 ]
Jacobson M, Sharma YR, Cotlier E, Hollander JD: Diabetic complications in lens and nerve and their prevention by sulindac or sorbinil: two novel aldose reductase inhibitors. Invest Ophthalmol Vis Sci. 1983 Oct;24(10):1426-9. [PubMed:6413448 ]
van der Sloot P, Mizisin A, Zochodne D: Sulindac in established experimental diabetes: a follow-up study. Can J Neurol Sci. 1995 Aug;22(3):198-201. [PubMed:8529171 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Giuliano F, Warner TD: Ex vivo assay to determine the cyclooxygenase selectivity of non-steroidal anti-inflammatory drugs. Br J Pharmacol. 1999 Apr;126(8):1824-30. [PubMed:10372826 ]
Molina MA, Sitja-Arnau M, Lemoine MG, Frazier ML, Sinicrope FA: Increased cyclooxygenase-2 expression in human pancreatic carcinomas and cell lines: growth inhibition by nonsteroidal anti-inflammatory drugs. Cancer Res. 1999 Sep 1;59(17):4356-62. [PubMed:10485483 ]
Yip-Schneider MT, Barnard DS, Billings SD, Cheng L, Heilman DK, Lin A, Marshall SJ, Crowell PL, Marshall MS, Sweeney CJ: Cyclooxygenase-2 expression in human pancreatic adenocarcinomas. Carcinogenesis. 2000 Feb;21(2):139-46. [PubMed:10657949 ]
Fosslien E: Biochemistry of cyclooxygenase (COX)-2 inhibitors and molecular pathology of COX-2 in neoplasia. Crit Rev Clin Lab Sci. 2000 Oct;37(5):431-502. [PubMed:11078056 ]
Taylor MT, Lawson KR, Ignatenko NA, Marek SE, Stringer DE, Skovan BA, Gerner EW: Sulindac sulfone inhibits K-ras-dependent cyclooxygenase-2 expression in human colon cancer cells. Cancer Res. 2000 Dec 1;60(23):6607-10. [PubMed:11118042 ]

Enzyme Details

3. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Giuliano F, Warner TD: Ex vivo assay to determine the cyclooxygenase selectivity of non-steroidal anti-inflammatory drugs. Br J Pharmacol. 1999 Apr;126(8):1824-30. [PubMed:10372826 ]
Lim JT, Piazza GA, Han EK, Delohery TM, Li H, Finn TS, Buttyan R, Yamamoto H, Sperl GJ, Brendel K, Gross PH, Pamukcu R, Weinstein IB: Sulindac derivatives inhibit growth and induce apoptosis in human prostate cancer cell lines. Biochem Pharmacol. 1999 Oct 1;58(7):1097-107. [PubMed:10484067 ]
Soriano AF, Helfrich B, Chan DC, Heasley LE, Bunn PA Jr, Chou TC: Synergistic effects of new chemopreventive agents and conventional cytotoxic agents against human lung cancer cell lines. Cancer Res. 1999 Dec 15;59(24):6178-84. [PubMed:10626810 ]
Cheng ZJ, Tikkanen I, Vapaatalo H, Mervaala EM: Vascular effects of COX inhibition and AT1 receptor blockade in transgenic rats harboring mouse renin-2 gene. J Physiol Pharmacol. 2002 Dec;53(4 Pt 1):597-613. [PubMed:12512695 ]
Cheng ZJ, Finckenberg P, Louhelainen M, Merasto S, Tikkanen I, Vapaatalo H, Mervaala EM: Cardiovascular and renal effects of cyclooxygenase inhibition in transgenic rats harboring mouse renin-2 gene (TGR[mREN2]27). Eur J Pharmacol. 2003 Feb 14;461(2-3):159-69. [PubMed:12586211 ]

Enzyme Details

4. Mitogen-activated protein kinase 3

General function:: Involved in MAP kinase activity
Specific function:: Involved in both the initiation and regulation of meiosis, mitosis, and postmitotic functions in differentiated cells by phosphorylating a number of transcription factors such as ELK-1. Phosphorylates EIF4EBP1; required for initiation of translation. Phosphorylates microtubule-associated protein 2 (MAP2). Phosphorylates SPZ1. Phosphorylates heat shock factor protein 4 (HSF4)
Gene Name:: MAPK3
Uniprot ID:: P27361
Molecular weight:: 43135.2

References

Rice PL, Goldberg RJ, Ray EC, Driggers LJ, Ahnen DJ: Inhibition of extracellular signal-regulated kinase 1/2 phosphorylation and induction of apoptosis by sulindac metabolites. Cancer Res. 2001 Feb 15;61(4):1541-7. [PubMed:11245463 ]
Rice PL, Washington M, Schleman S, Beard KS, Driggers LJ, Ahnen DJ: Sulindac sulfide inhibits epidermal growth factor-induced phosphorylation of extracellular-regulated kinase 1/2 and Bad in human colon cancer cells. Cancer Res. 2003 Feb 1;63(3):616-20. [PubMed:12566304 ]
Rice PL, Beard KS, Driggers LJ, Ahnen DJ: Inhibition of extracellular-signal regulated kinases 1/2 is required for apoptosis of human colon cancer cells in vitro by sulindac metabolites. Cancer Res. 2004 Nov 15;64(22):8148-51. [PubMed:15548677 ]
Pangburn HA, Kraus H, Ahnen DJ, Rice PL: Sulindac metabolites inhibit epidermal growth factor receptor activation and expression. J Carcinog. 2005 Sep 2;4:16. [PubMed:16138927 ]
Rice PL, Peters SL, Beard KS, Ahnen DJ: Sulindac independently modulates extracellular signal-regulated kinase 1/2 and cyclic GMP-dependent protein kinase signaling pathways. Mol Cancer Ther. 2006 Mar;5(3):746-54. [PubMed:16546990 ]

Enzyme Details

5. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

7. Peroxisome proliferator-activated receptor delta

General function:: Involved in DNA binding
Specific function:: Ligand-activated transcription factor. Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-linoleic acid and eicosapentanoic acid. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the acyl-CoA oxidase gene. Decreases expression of NPC1L1 once activated by a ligand
Gene Name:: PPARD
Uniprot ID:: Q03181
Molecular weight:: 49903.0

References

He TC, Chan TA, Vogelstein B, Kinzler KW: PPARdelta is an APC-regulated target of nonsteroidal anti-inflammatory drugs. Cell. 1999 Oct 29;99(3):335-45. [PubMed:10555149 ]
Babbar N, Ignatenko NA, Casero RA Jr, Gerner EW: Cyclooxygenase-independent induction of apoptosis by sulindac sulfone is mediated by polyamines in colon cancer. J Biol Chem. 2003 Nov 28;278(48):47762-75. Epub 2003 Sep 23. [PubMed:14506281 ]
Jarvis MC, Gray TJ, Palmer CN: Both PPARgamma and PPARdelta influence sulindac sulfide-mediated p21WAF1/CIP1 upregulation in a human prostate epithelial cell line. Oncogene. 2005 Dec 8;24(55):8211-5. [PubMed:16091736 ]
Kim DJ, Prabhu KS, Gonzalez FJ, Peters JM: Inhibition of chemically induced skin carcinogenesis by sulindac is independent of peroxisome proliferator-activated receptor-beta/delta (PPARbeta/delta). Carcinogenesis. 2006 May;27(5):1105-12. Epub 2006 Jan 16. [PubMed:16418176 ]
Liou JY, Ghelani D, Yeh S, Wu KK: Nonsteroidal anti-inflammatory drugs induce colorectal cancer cell apoptosis by suppressing 14-3-3epsilon. Cancer Res. 2007 Apr 1;67(7):3185-91. [PubMed:17409426 ]

Enzyme Details

8. Putative G-protein coupled receptor 44

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Orphan receptor
Gene Name:: GPR44
Uniprot ID:: Q9Y5Y4
Molecular weight:: 43267.2

References

Hata AN, Lybrand TP, Marnett LJ, Breyer RM: Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2. Mol Pharmacol. 2005 Mar;67(3):640-7. Epub 2004 Nov 24. [PubMed:15563582 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. [PubMed:9880528 ]

Showing metabocard for Sulindac (HMDB0014743)

MOL for HMDB0014743 (Sulindac)

3D MOL for HMDB0014743 (Sulindac)

3D SDF for HMDB0014743 (Sulindac)

3D-SDF for HMDB0014743 (Sulindac)

PDB for HMDB0014743 (Sulindac)

3D PDB for HMDB0014743 (Sulindac)

SMILES for HMDB0014743 (Sulindac)

INCHI for HMDB0014743 (Sulindac)

Structure for HMDB0014743 (Sulindac)

3D Structure for HMDB0014743 (Sulindac)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

Transporters

References