Bovine Metabolome Database: Showing metabocard for Rosiglitazone (BMDB0005031)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:14:49 UTC

Update Date

2020-04-22 15:15:10 UTC

BMDB ID

BMDB0005031

Secondary Accession Numbers

BMDB05031

Metabolite Identification

Common Name

Rosiglitazone

Description

Rosiglitazone, also known as BRL-49653 or gaudil, belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. Rosiglitazone is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-((4-(2-(Methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione	ChEBI
BRL-49653	ChEBI
Rosiglitazona	ChEBI
Rosiglitazonum	ChEBI
Gaudil	Kegg
Avandia	HMDB
Rosiglitazone maleate	HMDB
Rosiglizole	HMDB
5-((4-(2-Methyl-2-(pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione-2-butenedioate	HMDB
GlaxoSmithKline brand OF rosiglitazone maleate	HMDB
SmithKline beecham brand OF rosiglitazone maleate	HMDB
Glaxo wellcome brand OF rosiglitazone maleate	HMDB

Chemical Formula

C₁₈H₁₉N₃O₃S

Average Molecular Weight

357.427

Monoisotopic Molecular Weight

357.114712179

IUPAC Name

5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione

Traditional Name

rosiglitazone

CAS Registry Number

122320-73-4

SMILES

CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1

InChI Identifier

InChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)

InChI Key

YASAKCUCGLMORW-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
Monocyclic benzene moiety
Pyridine
Imidolactam
Heteroaromatic compound
Meta-thiazoline
Carbonic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aminopyridine (CHEBI:50122 )
thiazolidenediones (CHEBI:50122 )

Ontology

Status

Expected but not Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.95	ALOGPS
logP	2.45	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	6.84	ChemAxon
pKa (Strongest Basic)	6.23	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	97.79 m³·mol⁻¹	ChemAxon
Polarizability	37.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-6931000000-a3ad698c8739c8f57e74	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0a4i-0109000000-d527d5c2b5f1de352264	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-0109000000-d527d5c2b5f1de352264	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4r-1609000000-585d240b82e4a1918a29	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-0309000000-a9fa2307075b611cffcc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-1009000000-991ab6592f05f0e9b3b4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-052r-0906000000-d2389ebced7cec4a890e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0119000000-afcd19b8a0a922a55f1a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0941000000-369864aa78ee259dca92	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-1910000000-f9a7e77fcdf7ededf79c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0439000000-ab505f9372d95dd2a762	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0k9l-4792000000-bfe60ce181bc6c7314cb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9500000000-9699ab9cf1188cacce3f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1159000000-cd81e0c7b3e3f0631336	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9242000000-b5f05b953b17b8f5dc01	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-1495c41f9621c21b07f3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0902000000-914f8b56c690e9af074d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0579000000-0ae28d63488de9c942ee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05g0-0910000000-de9d0cd74d041cf2fe82	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0005031

DrugBank ID

DB00412

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023598

KNApSAcK ID

Not Available

Chemspider ID

70383

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rosiglitazone

METLIN ID

Not Available

PubChem Compound

77999

PDB ID

Not Available

ChEBI ID

50122

References

Synthesis Reference

Manne Reddy, "Amorphous form of rosiglitazone maleate and process for preparation thereof." U.S. Patent US20040242658, issued December 02, 2004.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Rosiglitazone (BMDB0005031)

Structure for BMDB0005031 (Rosiglitazone)