Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:02:38 UTC
Update Date2021-09-14 14:58:38 UTC
HMDB IDHMDB0060836
Secondary Accession Numbers
  • HMDB60836
Metabolite Identification
Common NameN-Desmethyl-O-hydroxy rosiglitazone
DescriptionN-Desmethyl-O-hydroxy rosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)
Structure
Data?1563866111
SynonymsNot Available
Chemical FormulaC17H17N3O4S
Average Molecular Weight359.4
Monoisotopic Molecular Weight359.093976737
IUPAC Name5-[(4-{2-[(3-hydroxypyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
Traditional Name5-[(4-{2-[(3-hydroxypyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
CAS Registry NumberNot Available
SMILES
OC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C1
InChI Identifier
InChI=1S/C17H17N3O4S/c21-13-2-1-7-18-15(13)19-8-9-24-12-5-3-11(4-6-12)10-14-16(22)20-17(23)25-14/h1-7,14,21H,8-10H2,(H,18,19)(H,20,22,23)
InChI KeyGWVBGLUFILBNNY-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
  • Aminopyridine
  • Hydroxypyridine
  • Thiazolidinedione
  • Secondary aliphatic/aromatic amine
  • Monocyclic benzene moiety
  • Imidolactam
  • Pyridine
  • Dicarboximide
  • Heteroaromatic compound
  • Thiazolidine
  • Amino acid or derivatives
  • Carbonic acid derivative
  • Thiocarbamic acid derivative
  • Carboxylic acid derivative
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
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 Solubility0.067 g/LALOGPS
logP2.33ALOGPS
logP1.41ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)7.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.55 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity95.54 m³·mol⁻¹ChemAxon
Polarizability36.87 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+183.16231661259
DarkChem[M-H]-178.59431661259
DeepCCS[M+H]+182.62330932474
DeepCCS[M-H]-180.15630932474
DeepCCS[M-2H]-214.03130932474
DeepCCS[M+Na]+189.5230932474
AllCCS[M+H]+183.432859911
AllCCS[M+H-H2O]+180.632859911
AllCCS[M+NH4]+186.132859911
AllCCS[M+Na]+186.932859911
AllCCS[M-H]-182.132859911
AllCCS[M+Na-2H]-181.932859911
AllCCS[M+HCOO]-181.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Desmethyl-O-hydroxy rosiglitazoneOC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C14645.5Standard polar33892256
N-Desmethyl-O-hydroxy rosiglitazoneOC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C13477.0Standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazoneOC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C13521.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Desmethyl-O-hydroxy rosiglitazone,1TMS,isomer #1C[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)NC2=O)C=C13704.5Semi standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,1TMS,isomer #2C[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=NC=CC=C1O3605.3Semi standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,1TMS,isomer #3C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCNC3=NC=CC=C3O)C=C2)C1=O3528.6Semi standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #1C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C3608.1Semi standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #1C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C3296.2Standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #1C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C4755.9Standard polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #2C[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C13523.8Semi standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #2C[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C13213.7Standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #2C[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C14442.0Standard polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #3C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C)C=C2)C1=O3371.8Semi standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #3C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C)C=C2)C1=O3295.4Standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #3C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C)C=C2)C1=O4402.1Standard polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,3TMS,isomer #1C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)[Si](C)(C)C3407.8Semi standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,3TMS,isomer #1C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)[Si](C)(C)C3287.2Standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,3TMS,isomer #1C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)[Si](C)(C)C4021.4Standard polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)NC2=O)C=C13956.8Semi standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=NC=CC=C1O3864.2Semi standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCNC3=NC=CC=C3O)C=C2)C1=O3803.8Semi standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C(C)(C)C4020.9Semi standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C(C)(C)C3649.6Standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C(C)(C)C4757.9Standard polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C13960.7Semi standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C13625.7Standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C14458.4Standard polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C(C)(C)C)C=C2)C1=O3860.1Semi standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C(C)(C)C)C=C2)C1=O3688.0Standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C(C)(C)C)C=C2)C1=O4373.8Standard polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)[Si](C)(C)C(C)(C)C4022.2Semi standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)[Si](C)(C)C(C)(C)C3845.8Standard non polar33892256
N-Desmethyl-O-hydroxy rosiglitazone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)[Si](C)(C)C(C)(C)C4135.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1961000000-bdb89099b5ab84dcf7432017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone GC-MS (1 TMS) - 70eV, Positivesplash10-00di-2955100000-bde6b78fb75b701962ad2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 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 - N-Desmethyl-O-hydroxy rosiglitazone 10V, Positive-QTOFsplash10-03di-0219000000-ab50299314a212f098be2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 20V, Positive-QTOFsplash10-000i-0974000000-2a33994dcccc3756ef032017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 40V, Positive-QTOFsplash10-01p9-3920000000-113ee2a6bfbed1aca6d52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 10V, Negative-QTOFsplash10-0a4i-0549000000-36b7007e3a7548658c8c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 20V, Negative-QTOFsplash10-0pbl-4591000000-9fddd5ced0e5ddb88dd52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 40V, Negative-QTOFsplash10-0006-9400000000-571bdbdbd29573e6abf82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 10V, Negative-QTOFsplash10-05fr-1098000000-7fbb6159e0a3d11a1b952021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 20V, Negative-QTOFsplash10-0006-9121000000-cac1b8fa1563e2c426d62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 40V, Negative-QTOFsplash10-0006-9200000000-2572c44b8781aa19bef12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 10V, Positive-QTOFsplash10-03di-0009000000-82b3876182bcc2781eaf2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 20V, Positive-QTOFsplash10-03dr-0977000000-a22398adddc85a82a31e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 40V, Positive-QTOFsplash10-00sa-2900000000-4b8e0a5a07e1cc80c35d2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 Compound86278298
PDB IDNot Available
ChEBI IDNot Available
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 ReferencesNot Available