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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 18:03:52 UTC

Update Date

2019-07-23 07:14:42 UTC

HMDB ID

HMDB0060614

Secondary Accession Numbers

HMDB60614

Metabolite Identification

Common Name

Sulindac sulfide

Description

Sulindac sulfide 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). Sulindac sulfide is a weakly acidic compound (based on its pKa).

Structure

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

HMDB0060614
     RDKit          3D
Sulindac sulfide
 41 43  0  0  0  0  0  0  0  0999 V2000
    6.0827   -1.9068   -1.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9802   -0.9571    0.5088 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3265   -0.2858    0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0372    0.9420    0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7533    1.4672    0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7386    0.7890    0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4576    1.3808    1.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6434    0.9380    0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9994    1.4980    0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2760    2.6835    1.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8819    0.8446   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548    1.1448   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1271   -0.0064    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8493   -0.7089   -0.3669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0379   -0.3085    1.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1800   -0.2111   -0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6394   -1.1398   -1.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428   -2.0103   -2.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859   -2.9289   -3.1650 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -1.9705   -1.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0736   -1.0187   -1.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8202   -0.1524   -0.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0295   -0.4486    1.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2962   -0.9724    1.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1537   -2.4773   -1.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9987   -2.5211   -1.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1675   -1.2139   -1.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8330    1.4758   -0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5281    2.4304   -0.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3430    2.2787    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715    3.3477    1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4320    2.3826    2.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0964    3.2808    1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6112    1.2878   -1.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5660    2.0315    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0536   -1.2578    2.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7007   -1.1545   -1.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3210   -2.6406   -2.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1066   -0.9880   -0.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2240   -0.9677    1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5203   -1.9559    1.7031 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  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 22  8  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 15 36  1  0
 17 37  1  0
 20 38  1  0
 21 39  1  0
 23 40  1  0
 24 41  1  0
M  END


  Mrv0541 06151311012D          

 24 26  0  0  0  0            999 V2000
   -1.4534   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536    1.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1014    2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4507    2.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2577    2.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5126    1.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9606    1.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8097    3.2065    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167    3.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9606   -2.5916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1014   -3.5477    0.0000 O   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
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  4 19  1  0  0  0  0
 18 20  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060614

> <DATABASE_NAME>
hmdb

> <SMILES>
CSC1=CC=C(\C=C2\C(C)=C(CC(O)=O)C3=C2C=CC(F)=C3)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H17FO2S/c1-12-17(9-13-3-6-15(24-2)7-4-13)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>
LFWHFZJPXXOYNR-MFOYZWKCSA-N

> <FORMULA>
C20H17FO2S

> <MOLECULAR_WEIGHT>
340.411

> <EXACT_MASS>
340.093328683

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.610924832742974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.77

> <JCHEM_LOGP>
4.8209571376666664

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.158019573321595

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
97.9561

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3Z)-6-fluoro-2-methyl-3-{[4-(methylsulfanyl)phenyl]methylidene}inden-1-yl]acetic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060614
     RDKit          3D
Sulindac sulfide
 41 43  0  0  0  0  0  0  0  0999 V2000
    6.0827   -1.9068   -1.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9802   -0.9571    0.5088 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3265   -0.2858    0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0372    0.9420    0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7533    1.4672    0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7386    0.7890    0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4576    1.3808    1.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6434    0.9380    0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9994    1.4980    0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2760    2.6835    1.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8819    0.8446   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548    1.1448   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1271   -0.0064    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8493   -0.7089   -0.3669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0379   -0.3085    1.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1800   -0.2111   -0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6394   -1.1398   -1.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428   -2.0103   -2.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859   -2.9289   -3.1650 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -1.9705   -1.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0736   -1.0187   -1.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8202   -0.1524   -0.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0295   -0.4486    1.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2962   -0.9724    1.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1537   -2.4773   -1.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9987   -2.5211   -1.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1675   -1.2139   -1.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8330    1.4758   -0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5281    2.4304   -0.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3430    2.2787    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715    3.3477    1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4320    2.3826    2.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0964    3.2808    1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6112    1.2878   -1.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5660    2.0315    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0536   -1.2578    2.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7007   -1.1545   -1.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3210   -2.6406   -2.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1066   -0.9880   -0.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2240   -0.9677    1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5203   -1.9559    1.7031 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  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 22  8  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 15 36  1  0
 17 37  1  0
 20 38  1  0
 21 39  1  0
 23 40  1  0
 24 41  1  0
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0      -2.713  -1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.287   2.552   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.189   4.017   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.841   5.161   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.348   4.841   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.824   3.376   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.793   2.232   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0       3.378   5.985   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       4.885   5.665   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   20  F   UNK     0       5.198  -2.843   0.000  0.00  0.00           F+0
HETATM   21  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.287  -5.158   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.793  -4.838   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.189  -6.622   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11   15                                                       
CONECT   15   14                                                            
CONECT   16    5   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18    4                                                       
CONECT   20   18                                                            
CONECT   21    3   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0060614
HETATM    1  C1  UNL     1       6.083  -1.907  -1.027  1.00  0.00           C  
HETATM    2  S1  UNL     1       5.980  -0.957   0.509  1.00  0.00           S  
HETATM    3  C2  UNL     1       4.327  -0.286   0.624  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.037   0.942   0.078  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.753   1.467   0.170  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.739   0.789   0.802  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.458   1.381   1.004  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.643   0.938   0.443  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.999   1.498   0.625  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.276   2.683   1.516  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.882   0.845  -0.092  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.355   1.145  -0.147  1.00  0.00           C  
HETATM   13  C12 UNL     1      -5.127  -0.006   0.379  1.00  0.00           C  
HETATM   14  O1  UNL     1      -5.849  -0.709  -0.367  1.00  0.00           O  
HETATM   15  O2  UNL     1      -5.038  -0.309   1.724  1.00  0.00           O  
HETATM   16  C13 UNL     1      -2.180  -0.211  -0.823  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.639  -1.140  -1.710  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.743  -2.010  -2.283  1.00  0.00           C  
HETATM   19  F1  UNL     1      -2.186  -2.929  -3.165  1.00  0.00           F  
HETATM   20  C16 UNL     1      -0.402  -1.970  -1.989  1.00  0.00           C  
HETATM   21  C17 UNL     1       0.074  -1.019  -1.076  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.820  -0.152  -0.500  1.00  0.00           C  
HETATM   23  C19 UNL     1       2.030  -0.449   1.352  1.00  0.00           C  
HETATM   24  C20 UNL     1       3.296  -0.972   1.263  1.00  0.00           C  
HETATM   25  H1  UNL     1       5.154  -2.477  -1.137  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.999  -2.521  -1.058  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.168  -1.214  -1.914  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.833   1.476  -0.418  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.528   2.430  -0.259  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.343   2.279   1.663  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.372   3.348   1.502  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.432   2.383   2.548  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.096   3.281   1.061  1.00  0.00           H  
HETATM   34  H10 UNL     1      -4.611   1.288  -1.227  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.566   2.031   0.453  1.00  0.00           H  
HETATM   36  H12 UNL     1      -5.054  -1.258   2.060  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.701  -1.155  -1.933  1.00  0.00           H  
HETATM   38  H14 UNL     1       0.321  -2.641  -2.429  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.107  -0.988  -0.895  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.224  -0.968   1.843  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.520  -1.956   1.703  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   24
CONECT    4    5   28
CONECT    5    6    6   29
CONECT    6    7   23
CONECT    7    8    8   30
CONECT    8    9   22
CONECT    9   10   11   11
CONECT   10   31   32   33
CONECT   11   12   16
CONECT   12   13   34   35
CONECT   13   14   14   15
CONECT   15   36
CONECT   16   17   17   22
CONECT   17   18   37
CONECT   18   19   20   20
CONECT   20   21   38
CONECT   21   22   22   39
CONECT   23   24   24   40
CONECT   24   41
END

HMDB0060614
     RDKit          3D
Sulindac sulfide
 41 43  0  0  0  0  0  0  0  0999 V2000
    6.0827   -1.9068   -1.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9802   -0.9571    0.5088 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3265   -0.2858    0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0372    0.9420    0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7533    1.4672    0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7386    0.7890    0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4576    1.3808    1.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6434    0.9380    0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9994    1.4980    0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2760    2.6835    1.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8819    0.8446   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548    1.1448   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1271   -0.0064    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8493   -0.7089   -0.3669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0379   -0.3085    1.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1800   -0.2111   -0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6394   -1.1398   -1.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428   -2.0103   -2.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859   -2.9289   -3.1650 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -1.9705   -1.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0736   -1.0187   -1.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8202   -0.1524   -0.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0295   -0.4486    1.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2962   -0.9724    1.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1537   -2.4773   -1.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9987   -2.5211   -1.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1675   -1.2139   -1.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8330    1.4758   -0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5281    2.4304   -0.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3430    2.2787    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715    3.3477    1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4320    2.3826    2.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0964    3.2808    1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6112    1.2878   -1.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5660    2.0315    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0536   -1.2578    2.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7007   -1.1545   -1.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3210   -2.6406   -2.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1066   -0.9880   -0.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2240   -0.9677    1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5203   -1.9559    1.7031 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  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 22  8  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 15 36  1  0
 17 37  1  0
 20 38  1  0
 21 39  1  0
 23 40  1  0
 24 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Sulindac sulphide	Generator
Sulindac sulfide, (Z)-isomer	HMDB
Sulindac sulfide, sodium salt	HMDB
Sulindac sulfide, (e)-isomer	HMDB

Chemical Formula

C₂₀H₁₇FO₂S

Average Molecular Weight

340.411

Monoisotopic Molecular Weight

340.093328683

IUPAC Name

2-[(1Z)-5-fluoro-2-methyl-1-{[4-(methylsulfanyl)phenyl]methylidene}-1H-inden-3-yl]acetic acid

Traditional Name

[(3Z)-6-fluoro-2-methyl-3-{[4-(methylsulfanyl)phenyl]methylidene}inden-1-yl]acetic acid

CAS Registry Number

Not Available

SMILES

CSC1=CC=C(\C=C2\C(C)=C(CC(O)=O)C3=C2C=CC(F)=C3)C=C1

InChI Identifier

InChI=1S/C20H17FO2S/c1-12-17(9-13-3-6-15(24-2)7-4-13)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

LFWHFZJPXXOYNR-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

Indene
Aryl thioether
Thiophenol ether
Alkylarylthioether
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Carboxylic acid derivative
Carboxylic acid
Sulfenyl compound
Monocarboxylic acid or derivatives
Thioether
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organohalogen compound
Organofluoride
Organooxygen compound
Organosulfur compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:75408 )
monocarboxylic acid (CHEBI:75408 )
aryl sulfide (CHEBI:75408 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060614)

Organ

Kidney (HMDB: HMDB0060614)
Liver (HMDB: HMDB0060614)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060614)

Cellular substructure

Cytoplasm (HMDB: HMDB0060614)
Membrane (HMDB: HMDB0060614)

Source

Endogenous

Endogenous (HMDB: HMDB0060614)

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	4.77	ALOGPS
logP	4.82	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.96 m³·mol⁻¹	ChemAxon
Polarizability	36.61 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	187.177	30932474
DeepCCS	[M-H]-	184.819	30932474
DeepCCS	[M-2H]-	218.906	30932474
DeepCCS	[M+Na]+	194.134	30932474
AllCCS	[M+H]+	180.4	32859911
AllCCS	[M+H-H2O]+	177.2	32859911
AllCCS	[M+NH4]+	183.3	32859911
AllCCS	[M+Na]+	184.2	32859911
AllCCS	[M-H]-	178.6	32859911
AllCCS	[M+Na-2H]-	177.8	32859911
AllCCS	[M+HCOO]-	177.1	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.	9.24 minutes	32390414
Predicted by Siyang on May 30, 2022	19.6686 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.84 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3264.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	617.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	235.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	336.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	451.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	955.0 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	948.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	132.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1838.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	678.4 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	1712.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	623.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	512.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	427.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	344.4 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sulindac sulfide	CSC1=CC=C(\C=C2\C(C)=C(CC(O)=O)C3=C2C=CC(F)=C3)C=C1	4977.9	Standard polar	33892256
Sulindac sulfide	CSC1=CC=C(\C=C2\C(C)=C(CC(O)=O)C3=C2C=CC(F)=C3)C=C1	2917.5	Standard non polar	33892256
Sulindac sulfide	CSC1=CC=C(\C=C2\C(C)=C(CC(O)=O)C3=C2C=CC(F)=C3)C=C1	3059.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sulindac sulfide,1TMS,isomer #1	CSC1=CC=C(/C=C2/C(C)=C(CC(=O)O[Si](C)(C)C)C3=CC(F)=CC=C23)C=C1	2989.3	Semi standard non polar	33892256
Sulindac sulfide,1TBDMS,isomer #1	CSC1=CC=C(/C=C2/C(C)=C(CC(=O)O[Si](C)(C)C(C)(C)C)C3=CC(F)=CC=C23)C=C1	3209.6	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 sulfide GC-MS (Non-derivatized) - 70eV, Positive	splash10-009y-1196000000-50ee17c1a16398b0046b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulindac sulfide GC-MS (1 TMS) - 70eV, Positive	splash10-006t-9056000000-43782503c8c4aaa3d307	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulindac sulfide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulindac sulfide 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 - Sulindac sulfide 10V, Positive-QTOF	splash10-006x-0039000000-9dd2cb3f01fc46a3e07f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac sulfide 20V, Positive-QTOF	splash10-0002-0293000000-537033a398334f5481d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac sulfide 40V, Positive-QTOF	splash10-00vj-3691000000-d879bfe476f8b1943865	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac sulfide 10V, Negative-QTOF	splash10-0005-3093000000-04aab094d4a271cf9afe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac sulfide 20V, Negative-QTOF	splash10-0005-1092000000-35efb69dbd70f0ef004a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac sulfide 40V, Negative-QTOF	splash10-0002-9010000000-41b8fa35ebb0450896ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac sulfide 10V, Positive-QTOF	splash10-0002-0095000000-d7c3564f1bf23d6bf384	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac sulfide 20V, Positive-QTOF	splash10-006w-0393000000-1fb1b3d71473194e8ac2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac sulfide 40V, Positive-QTOF	splash10-0012-1090000000-7c1f83cd23ca6418c5fa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac sulfide 10V, Negative-QTOF	splash10-000b-0098000000-d9466c08006e9eeb4389	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac sulfide 20V, Negative-QTOF	splash10-0002-1090000000-9286255bce992fc68bdb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulindac sulfide 40V, Negative-QTOF	splash10-0002-1091000000-e6bbdbbffc304c285a14	2021-10-12	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

5352624

PDB ID

Not Available

ChEBI ID

75408

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

Chiou SK, Hoa N, Hodges A: Sulindac sulfide induces autophagic death in gastric epithelial cells via survivin down-regulation: a mechanism of NSAIDs-induced gastric injury. Biochem Pharmacol. 2011 Jun 1;81(11):1317-23. doi: 10.1016/j.bcp.2011.03.019. Epub 2011 Mar 30. [PubMed:21458423 ]
Guillen-Ahlers H, Tan J, Castellino FJ, Ploplis VA: Effect of sulindac sulfide on metallohydrolases in the human colon cancer cell line HT-29. PLoS One. 2011;6(10):e25725. doi: 10.1371/journal.pone.0025725. Epub 2011 Oct 3. [PubMed:21991341 ]
Gurpinar E, Grizzle WE, Shacka JJ, Mader BJ, Li N, Piazza NA, Russo S, Keeton AB, Piazza GA: A novel sulindac derivative inhibits lung adenocarcinoma cell growth through suppression of Akt/mTOR signaling and induction of autophagy. Mol Cancer Ther. 2013 May;12(5):663-74. doi: 10.1158/1535-7163.MCT-12-0785. Epub 2013 Feb 26. [PubMed:23443799 ]

Showing metabocard for Sulindac sulfide (HMDB0060614)

MOL for HMDB0060614 (Sulindac sulfide)

3D MOL for HMDB0060614 (Sulindac sulfide)

3D SDF for HMDB0060614 (Sulindac sulfide)

3D-SDF for HMDB0060614 (Sulindac sulfide)

PDB for HMDB0060614 (Sulindac sulfide)

3D PDB for HMDB0060614 (Sulindac sulfide)

SMILES for HMDB0060614 (Sulindac sulfide)

INCHI for HMDB0060614 (Sulindac sulfide)

Structure for HMDB0060614 (Sulindac sulfide)

3D Structure for HMDB0060614 (Sulindac sulfide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra