Sulindac sulfide (CHEM020287)

Record Information
Version1.0
Creation Date2016-05-22 06:58:48 UTC
Update Date2026-08-20 04:58:58 UTC
Accession NumberCHEM020287
Identification
Common NameSulindac sulfide
ClassSmall Molecule
Description
An aryl sulfide that is a metabolite of sulindac. A non-steroidal anti-inflammatory drug, which also has anticancer activity.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Sulindac sulphideGenerator
Sulindac sulfide, (Z)-isomerHMDB
Sulindac sulfide, sodium saltHMDB
Sulindac sulfide, (e)-isomerHMDB
Chemical FormulaC20H17FO2S
Average Molecular Mass340.411 g/mol
Monoisotopic Mass340.093 g/mol
CAS Registry Number49627-27-2
IUPAC Name2-[(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
SMILESCSC1=CC=C(\C=C2\C(C)=C(CC(O)=O)C3=C2C=CC(F)=C3)C=C1
InChI IdentifierInChI=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 KeyLFWHFZJPXXOYNR-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).
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndenes and isoindenes
Sub ClassNot Available
Direct ParentIndenes 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 FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0035 g/LALOGPS
logP4.77ALOGPS
logP4.82ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity97.96 m³·mol⁻¹ChemAxon
Polarizability36.61 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0060614
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID75408
PubChem Compound ID5352624
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21458423
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21991341
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23202471
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23280445
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23443799
6. 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.
7. 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.
8. 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.