Sulindac sulfide (CHEM020287)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:58:48 UTC
Update Date2016-11-09 01:16:10 UTC
Accession NumberCHEM020287
Identification
Common NameSulindac sulfide
ClassSmall Molecule
DescriptionAn 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
Thumb
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-009y-1196000000-50ee17c1a16398b0046bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006t-9056000000-43782503c8c4aaa3d307Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0039000000-9dd2cb3f01fc46a3e07fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0293000000-537033a398334f5481d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00vj-3691000000-d879bfe476f8b1943865Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0005-3093000000-04aab094d4a271cf9afeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-1092000000-35efb69dbd70f0ef004aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9010000000-41b8fa35ebb0450896baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0095000000-d7c3564f1bf23d6bf384Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006w-0393000000-1fb1b3d71473194e8ac2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0012-1090000000-7c1f83cd23ca6418c5faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-0098000000-d9466c08006e9eeb4389Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1090000000-9286255bce992fc68bdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1091000000-e6bbdbbffc304c285a14Spectrum
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
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.