Ciglitizone (CHEM017608)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:29:39 UTC
Update Date2016-11-09 01:15:37 UTC
Accession NumberCHEM017608
Identification
Common NameCiglitizone
ClassSmall Molecule
DescriptionAn aromatic ether that consists of 1,3-thiazolidine-2,4-dione with position 5 substituted by a 4-benzyl group. A selective PPARgamma agonist.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(+-)-5-(p-((1-Methylcyclohexyl)methoxy)benzyl)-2,4-thiazolidinedioneChEBI
CiglitazonaChEBI
CiglitazonumChEBI
5-(4-(1-Methylcyclohexylmethoxy)benzyl)thiazolidine-2,4-dioneMeSH
CiglitizoneMeSH
Chemical FormulaC18H23NO3S
Average Molecular Mass333.450 g/mol
Monoisotopic Mass333.140 g/mol
CAS Registry Number74772-77-3
IUPAC Name5-({4-[(1-methylcyclohexyl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
Traditional Nameciglitazone
SMILESCC1(COC2=CC=C(CC3SC(=O)NC3=O)C=C2)CCCCC1
InChI IdentifierInChI=1S/C18H23NO3S/c1-18(9-3-2-4-10-18)12-22-14-7-5-13(6-8-14)11-15-16(20)19-17(21)23-15/h5-8,15H,2-4,9-12H2,1H3,(H,19,20,21)
InChI KeyYZFWTZACSRHJQD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Thiazolidinedione
  • Monocyclic benzene moiety
  • Dicarboximide
  • Thiazolidine
  • Thiocarbamic acid derivative
  • Carbonic acid derivative
  • Organoheterocyclic compound
  • Ether
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility0.0053 g/LALOGPS
logP3.93ALOGPS
logP4.28ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)6.61ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.4 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity91.26 m³·mol⁻¹ChemAxon
Polarizability36.36 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-7391000000-ae2a3af7ade94373a27fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1429000000-28e1f85607c05c8f4472Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2693000000-031d8ee657c7a0bde80cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-9610000000-b64415d0e331ca4bcacaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0179000000-bc180035e574e278e038Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4392000000-3b161add5ed819dfc42eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-3d9dfa97e4767c61a9d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-cb620b44b0b90e4a2419Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0292000000-4d00ec17a64b535c764aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9100000000-b827d741badd527053abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1019000000-aac91586dd95f8aa046bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9050000000-ed6920b734f9c97ef743Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-27eec2858ac76d50831aSpectrum
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 IDDB09201
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCiglitazone
Chemspider IDNot Available
ChEBI ID64227
PubChem Compound ID2750
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=20596077
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21067863
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21344384
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21354099
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21485077
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21508362
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21681689
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21882481
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22007221
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22131991
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22174792
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22177955
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22192353
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22193206
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22268140