ContaminantDB: 5-Hydroxy Rosiglitazone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 03:30:50 UTC

Update Date

2016-10-28 10:04:18 UTC

Accession Number

CHEM021430

Identification

Common Name

5-Hydroxy Rosiglitazone

Class

Small Molecule

Description

para-hydroxyrosiglitazone 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)

Contaminant Sources

Suspected Compounds - Waste Water

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Hydroxyrosiglitazone	HMDB

Chemical Formula

C₁₈H₁₉N₃O₄S

Average Molecular Mass

373.426 g/mol

Monoisotopic Mass

373.110 g/mol

CAS Registry Number

Not Available

IUPAC Name

4-hydroxy-5-[(4-{2-[(5-hydroxypyridin-2-yl)(methyl)amino]ethoxy}phenyl)methyl]-2,5-dihydro-1,3-thiazol-2-one

Traditional Name

4-hydroxy-5-[(4-{2-[(5-hydroxypyridin-2-yl)(methyl)amino]ethoxy}phenyl)methyl]-5H-1,3-thiazol-2-one

SMILES

CN(CCOC1=CC=C(CC2SC(=O)N=C2O)C=C1)C1=NC=C(O)C=C1

InChI Identifier

InChI=1S/C18H19N3O4S/c1-21(16-7-4-13(22)11-19-16)8-9-25-14-5-2-12(3-6-14)10-15-17(23)20-18(24)26-15/h2-7,11,15,22H,8-10H2,1H3,(H,20,23,24)

InChI Key

AGQGGZNSVNKGDU-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol ethers

Alternative Parents

Substituents

Phenoxy compound
Phenol ether
Dialkylarylamine
Alkyl aryl ether
Aminopyridine
Hydroxypyridine
Thiazolidinedione
Monocyclic benzene moiety
Pyridine
Imidolactam
Dicarboximide
Heteroaromatic compound
Thiazolidine
Carbonic acid derivative
Thiocarbamic acid derivative
Carboxylic acid derivative
Ether
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	2.69	ALOGPS
logP	2.38	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	5.72	ChemAxon
pKa (Strongest Basic)	6.39	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.25 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	100.09 m³·mol⁻¹	ChemAxon
Polarizability	38.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05g0-3942000000-fc10c40b90234178d99d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0zir-6592050000-8dc5980a48c464d30de1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0329000000-402824245bbf3f868cf7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uk9-4958000000-1ea7f0acc33233f3e980	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-ad5f3201e0a83fb6e946	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-c160455495ce5cf1fa47	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fdo-4119000000-199103e7183f2597fe54	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-580b3d271ae99a434b7b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0119000000-cfcb5cc55351ac9b428f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0924000000-3d58818d4a0783fbf596	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-0910000000-d69e07efbe51090c154b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-0904000000-a448b41bc3f462e409d4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0917000000-dfe52a04454c09025f42	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-236c54e7fad831b39cee	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0060981

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

9864316

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

5-Hydroxy Rosiglitazone (CHEM021430)

Structure for CHEM021430: 5-Hydroxy Rosiglitazone