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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 21:48:36 UTC
Update Date2022-11-23 22:29:21 UTC
HMDB IDHMDB0259292
Secondary Accession NumbersNone
Metabolite Identification
Common NameTroglitazone
DescriptionTroglitazone, also known as rezulin, belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. Troglitazone is a drug which is used for the treatment of type ii diabetes mellitus. it is used alone or in combination with a sulfonylurea, metformin, or insulin as an adjunct to diet and exercise. Based on a literature review very few articles have been published on Troglitazone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Troglitazone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Troglitazone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
RezulinChEBI
RomglizoneChEBI
TroglitazonaChEBI
TroglitazonumChEBI
PrelayMeSH
Warner-lambert brand OF troglitazoneMeSH
Parke davis brand OF troglitazoneMeSH
Chemical FormulaC24H27NO5S
Average Molecular Weight441.54
Monoisotopic Molecular Weight441.160993669
IUPAC Name5-({4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
Traditional Nametroglitazone
CAS Registry NumberNot Available
SMILES
CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)NC4=O)C=C3)O2)C(C)=C1O
InChI Identifier
InChI=1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28)
InChI KeyGXPHKUHSUJUWKP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent1-benzopyrans
Alternative Parents
Substituents
  • 1-benzopyran
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Thiazolidinedione
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboximide
  • Thiazolidine
  • Carbonic acid derivative
  • Thiocarbamic acid derivative
  • Carboxylic acid derivative
  • Ether
  • Oxacycle
  • Azacycle
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP4.16ALOGPS
logP5.5ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)6.61ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.86 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.99 m³·mol⁻¹ChemAxon
Polarizability47.08 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+207.67730932474
DeepCCS[M-H]-205.31930932474
DeepCCS[M-2H]-239.15930932474
DeepCCS[M+Na]+214.97330932474
AllCCS[M+H]+208.032859911
AllCCS[M+H-H2O]+205.832859911
AllCCS[M+NH4]+210.132859911
AllCCS[M+Na]+210.632859911
AllCCS[M-H]-202.732859911
AllCCS[M+Na-2H]-202.932859911
AllCCS[M+HCOO]-203.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
troglitazoneCC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)NC4=O)C=C3)O2)C(C)=C1O5283.1Standard polar33892256
troglitazoneCC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)NC4=O)C=C3)O2)C(C)=C1O3857.0Standard non polar33892256
troglitazoneCC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)NC4=O)C=C3)O2)C(C)=C1O3996.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
troglitazone,2TMS,isomer #1CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C3787.1Semi standard non polar33892256
troglitazone,2TMS,isomer #1CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C3580.1Standard non polar33892256
troglitazone,2TMS,isomer #1CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C4173.1Standard polar33892256
troglitazone,2TBDMS,isomer #1CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C(C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C(C)(C)C4226.5Semi standard non polar33892256
troglitazone,2TBDMS,isomer #1CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C(C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C(C)(C)C3959.0Standard non polar33892256
troglitazone,2TBDMS,isomer #1CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)N([Si](C)(C)C(C)(C)C)C4=O)C=C3)O2)C(C)=C1O[Si](C)(C)C(C)(C)C4270.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Troglitazone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-1889600000-e7d440741c30fa7019972021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troglitazone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troglitazone GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troglitazone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troglitazone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troglitazone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Troglitazone 60V, Negative-QTOFsplash10-0f6t-1900000000-b41d1d9b00383779a8be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Troglitazone 45V, Negative-QTOFsplash10-0f6t-0900000000-ab7c5539034df635ac142021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Troglitazone 75V, Negative-QTOFsplash10-0fr2-1900000000-1a1e22916ed5413720eb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Troglitazone 90V, Negative-QTOFsplash10-014j-2900000000-52697cbd413c9fbe49f82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Troglitazone 30V, Negative-QTOFsplash10-0005-1507900000-4f7d34b5dc4e0c481b682021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Troglitazone 15V, Negative-QTOFsplash10-0006-0000900000-8c86a1f2bb9af73c4ae92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Troglitazone 60V, Positive-QTOFsplash10-014i-1900000000-c7a1ca757fec1b1a4e5e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Troglitazone 75V, Positive-QTOFsplash10-014i-3900000000-c72fbe14217a1770ef4d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troglitazone 10V, Positive-QTOFsplash10-0006-0430900000-ceb18bd79d0f6da79e7d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troglitazone 20V, Positive-QTOFsplash10-014i-0912100000-c1ddd0b2276cc0642c282016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troglitazone 40V, Positive-QTOFsplash10-0bt9-0910000000-70eed845667711a7ff742016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troglitazone 10V, Negative-QTOFsplash10-0006-0133900000-d4c360adbc610d5363cf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troglitazone 20V, Negative-QTOFsplash10-0v4l-4759300000-7eda5e5df7869dbcd5692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troglitazone 40V, Negative-QTOFsplash10-0006-9700000000-bbf919843d75c50ea8132016-08-03Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00197
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5389
KEGG Compound IDNot Available
BioCyc IDCPD-11439
BiGG IDNot Available
Wikipedia LinkTroglitazone
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID9753
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]