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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 18:03:52 UTC
Update Date2019-07-23 07:14:42 UTC
HMDB IDHMDB0060614
Secondary Accession Numbers
  • HMDB60614
Metabolite Identification
Common NameSulindac sulfide
DescriptionSulindac 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
Data?1563866082
Synonyms
ValueSource
Sulindac sulphideGenerator
Sulindac sulfide, (Z)-isomerHMDB
Sulindac sulfide, sodium saltHMDB
Sulindac sulfide, (e)-isomerHMDB
Chemical FormulaC20H17FO2S
Average Molecular Weight340.411
Monoisotopic Molecular Weight340.093328683
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
CAS Registry NumberNot 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 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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+187.17730932474
DeepCCS[M-H]-184.81930932474
DeepCCS[M-2H]-218.90630932474
DeepCCS[M+Na]+194.13430932474
AllCCS[M+H]+180.432859911
AllCCS[M+H-H2O]+177.232859911
AllCCS[M+NH4]+183.332859911
AllCCS[M+Na]+184.232859911
AllCCS[M-H]-178.632859911
AllCCS[M+Na-2H]-177.832859911
AllCCS[M+HCOO]-177.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Sulindac sulfideCSC1=CC=C(\C=C2\C(C)=C(CC(O)=O)C3=C2C=CC(F)=C3)C=C14977.9Standard polar33892256
Sulindac sulfideCSC1=CC=C(\C=C2\C(C)=C(CC(O)=O)C3=C2C=CC(F)=C3)C=C12917.5Standard non polar33892256
Sulindac sulfideCSC1=CC=C(\C=C2\C(C)=C(CC(O)=O)C3=C2C=CC(F)=C3)C=C13059.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sulindac sulfide,1TMS,isomer #1CSC1=CC=C(/C=C2/C(C)=C(CC(=O)O[Si](C)(C)C)C3=CC(F)=CC=C23)C=C12989.3Semi standard non polar33892256
Sulindac sulfide,1TBDMS,isomer #1CSC1=CC=C(/C=C2/C(C)=C(CC(=O)O[Si](C)(C)C(C)(C)C)C3=CC(F)=CC=C23)C=C13209.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sulindac sulfide GC-MS (Non-derivatized) - 70eV, Positivesplash10-009y-1196000000-50ee17c1a16398b0046b2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulindac sulfide GC-MS (1 TMS) - 70eV, Positivesplash10-006t-9056000000-43782503c8c4aaa3d3072017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulindac sulfide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulindac sulfide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulindac sulfide 10V, Positive-QTOFsplash10-006x-0039000000-9dd2cb3f01fc46a3e07f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulindac sulfide 20V, Positive-QTOFsplash10-0002-0293000000-537033a398334f5481d42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulindac sulfide 40V, Positive-QTOFsplash10-00vj-3691000000-d879bfe476f8b19438652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulindac sulfide 10V, Negative-QTOFsplash10-0005-3093000000-04aab094d4a271cf9afe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulindac sulfide 20V, Negative-QTOFsplash10-0005-1092000000-35efb69dbd70f0ef004a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulindac sulfide 40V, Negative-QTOFsplash10-0002-9010000000-41b8fa35ebb0450896ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulindac sulfide 10V, Positive-QTOFsplash10-0002-0095000000-d7c3564f1bf23d6bf3842021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulindac sulfide 20V, Positive-QTOFsplash10-006w-0393000000-1fb1b3d71473194e8ac22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulindac sulfide 40V, Positive-QTOFsplash10-0012-1090000000-7c1f83cd23ca6418c5fa2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulindac sulfide 10V, Negative-QTOFsplash10-000b-0098000000-d9466c08006e9eeb43892021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulindac sulfide 20V, Negative-QTOFsplash10-0002-1090000000-9286255bce992fc68bdb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulindac sulfide 40V, Negative-QTOFsplash10-0002-1091000000-e6bbdbbffc304c285a142021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5352624
PDB IDNot Available
ChEBI ID75408
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]