UCSF

ZINC00968328

Substance Information

In ZINC since Heavy atoms Benign functionality
November 8th, 2004 25 No

Other Names:

(+ -)-5-[[4-2-(methyl]-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione,(Z)-2-butenedioate (1:1); (+-)-5-(p-(2-(Methyl-2-pyridylamino)ethoxy)benzyl)-2,4-thiazolidinedione maleate (1:1); 2,4-Thiazolidinedione, 5-((4-(2-(methyl-2-pyridinylamino)

(-)-rosiglitazone

glitazone

122320-73-4

122320-73-4; D08491; Gaudil (TN); Rosiglitazone (INN)

155141-29-0; Avandia (TN); D00596; Rosiglitazone maleate (JAN/USAN)

2,4-Thiazolidinedione, 5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-

2,4-Thiazolidinedione, 5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-; 2,4-Thiazolidinedione, 5-004-02-((((methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-; 5-((4-(2-Methyl-2-(pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione-2-butenedioa

2,4-Thiazolidinedione, 5-004-02-((((methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-

2,4-thiazolidinedione, 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-

2,4-Thiazolidinedione, 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]- (9CI)

5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione

5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione; BRL-49653

5-((4-(2-Methyl-2-(pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione-2-butenedioate

5-(4-(2-(Methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione

5-(4-(2-(Methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione hydrochloride

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

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

5-[4-[2-(N-Methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione

5-[4-[2-[methyl(2-pyridyl)amino]ethoxy]benzyl]thiazolidine-2,4-quinone

5-[[4-[2-(methyl-(2-pyridyl)amino)ethoxy]phenyl]methyl] thiazolidine-2,4-dione

5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]-phenyl]methyl]-2,4-thiazolidine-dione

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

AC-3459

AC1L2U9N

Avandia

Avandia;Rosiglitazone maleate;Rosiglizole

BRD-A97437073-001-02-3

BRD-A97437073-001-03-1

Brl 49653

BRL 49653C; rosiglitazone maleate

BRL-49653

BRL-49653; BRL-49653-C; BRL-49653C

BRL-49653C

BRL49653

BSPBio_002693

C18H19N3O3S

CHEBI:50124; CHEBI:41217

CID77999

CPD000471612; ROSIGLITAZONE MALEATE

CPD000471612; ROSIGLITAZONE MALEATE; SAM001246610

D08491

DAP000271

DB00412

FDA)

Gaudil

Gaudil (TN)

HMS1922J11

HMS2094O13

HSDB 7555

I06-0141

IDMB (1uM BRL49653, 1uM Dexamethasone, 0.5uM IBMX, 10ug/mL Insulin)

INN)

INN); Rosiglitazone maleate (FDA

INN); Rosiglitazone Maleate (USAN

KBio2_002183

KBio2_004751

KBio2_007319

KBio3_001913

KBioGR_001609

KBioSS_002183

LS-151340

LS-188034; METFORMIN HYDROCHLORIDE; ROSIGLITAZONE MALEATE; ROSIGLITAZONE MALEATE; METFORMIN HYDROCHLORIDE

MFCD00871760

MFCD03427306

MFCD04112701

MFCD09751028

MolPort-002-508-212

N/A

NA

NCGC00095124-01

NCGC00095124-02

NCGC00095124-03

Nyracta

QA-3573

RGZ

Rosi

Rosigilitazone

Rosigliazone maleate

rosiglitazona

rosiglitazona; rosiglitazone; rosiglitazonum

rosiglitazone (Avandia)

Rosiglitazone (BAN

Rosiglitazone (INN)

Rosiglitazone Hydrochloride

Rosiglitazone Maleate

Rosiglitazone Maleate (FDA

Rosiglitazone sodium

Rosiglitazone [INN:BAN]

Rosiglitazone(potassiumsalt)

rosiglitazone, 99%+

RosiglitazoneMaleate

rosiglitazonum

Rosiglizole

Rosigtitazone

RSG

S00306

SB-206846

SB-210232

SPBio_001142

SPECTRUM1504263

Spectrum2_001241

Spectrum3_000997

Spectrum4_001125

Spectrum5_001464

Spectrum_001703

STOCK6S-23924

TDZ 01

UNII-05V02F2KDG

USAN)

USAN); Rosiglitazone (BAN

Venvia

[3H]rosiglitazone

Download: MOL2 SDF SMILES Flexibase

Annotations

Vendors

Physical Representations

Type pH range xlogP Des A‑Pol Apolar desolvation (kcal/mol) Des Pol Polar desolvation (kcal/mol) H Don H-bond donors H Acc H-bond acceptors Chg Net charge tPSA (Ų) MWT Molecular weight (g/mol) RB Rotatable bonds DL
Ref Reference (pH 7) 2.35 7.4 -33.54 2 6 1 73 358.443 7
Mid Mid (pH 6-8) 2.35 7.28 -11.07 1 6 0 72 357.435 7

Vendor Notes

Note Type Comments Provided By
ALOGPS_SOLUBILITY 3.80e-02 g/l DrugBank-approved
purity 9.500000000000000e+001 Enamine Building Blocks Enamine Building Blocks
Purity 95% Fluorochem
Purity 98% Fluorochem
UniProt Database Links ABHDB_MOUSE; CIDEA_MOUSE; CIDEC_MOUSE; PLPL2_RAT ChEBI
Therapy antidiabetic SMDC MicroSource
Patent Database Links EP1088824; EP1136071; EP1254667; EP1258253; EP1338600; EP1354882; EP1391460; EP1411055; EP1468997; EP1491541; EP1493448; EP1514550; EP1522310; EP1537858; EP1538164; EP1559710; EP1595544; EP1607396; EP1625847; EP1634605; EP1642593; EP1652913; EP1688148; EP ChEBI
Patent Database Links EP1468997; EP1553091; EP1854794; EP1884513; US2005014798; US2006264639; US2007225337; US2007265313; WO2005095390; WO2005105794; WO2006010653; WO2006125402 ChEBI
PUBCHEM_SUBSTANCE_COMMENT NCC_SAMPLE_SUPPLIER : Sequoia Research Products Ltd.; NCC_SUPPLIER_STRUCTURE_ID : SRP01315r; 1 maleic acid NIH Clinical Collection via PubChem
Target PPAR Selleck Chemicals
Reactome Database Links REACT_15291; REACT_19346; REACT_19366; REACT_21412; REACT_22263; REACT_22436; REACT_27257 ChEBI
PUBCHEM_SUBSTANCE_COMMENT SAMPLE_SUPPLIER: Sequoia Research Products Ltd.; SUPPLIER_STRUCTURE_ID: SRP01315r; SALT: 1 maleic acid NIH Clinical Collection via PubChem

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
AOFB-2-E Monoamine Oxidase B (cluster #2 Of 8), Eukaryotic Eukaryotes 832 0.34 Binding ≤ 10μM
PPARA-1-E Peroxisome Proliferator-activated Receptor Alpha (cluster #1 Of 3), Eukaryotic Eukaryotes 4100 0.30 Binding ≤ 10μM
PPARD-2-E Peroxisome Proliferator-activated Receptor Delta (cluster #2 Of 2), Eukaryotic Eukaryotes 3620 0.30 Binding ≤ 10μM
PPARG-1-E Peroxisome Proliferator-activated Receptor Gamma (cluster #1 Of 2), Eukaryotic Eukaryotes 14 0.44 Binding ≤ 10μM
PPARG-1-E Peroxisome Proliferator-activated Receptor Gamma (cluster #1 Of 2), Eukaryotic Eukaryotes 60 0.40 Binding ≤ 10μM
RARG-1-E Retinoic Acid Receptor Gamma (cluster #1 Of 2), Eukaryotic Eukaryotes 10000 0.28 Binding ≤ 10μM
RXRA-1-E Retinoid X Receptor Alpha (cluster #1 Of 1), Eukaryotic Eukaryotes 325 0.36 Binding ≤ 10μM
PPARA-1-E Peroxisome Proliferator-activated Receptor Alpha (cluster #1 Of 2), Eukaryotic Eukaryotes 4100 0.30 Functional ≤ 10μM
PPARG-2-E Peroxisome Proliferator-activated Receptor Gamma (cluster #2 Of 2), Eukaryotic Eukaryotes 76 0.40 Functional ≤ 10μM
PPARG-2-E Peroxisome Proliferator-activated Receptor Gamma (cluster #2 Of 2), Eukaryotic Eukaryotes 210 0.37 Functional ≤ 10μM
Z80106-1-O COS-1 (Kidney Cells) (cluster #1 Of 1), Other Other 23 0.43 Functional ≤ 10μM
Z80169-1-O Huh-7 (Hepatocellular Carcinoma) (cluster #1 Of 1), Other Other 220 0.37 Functional ≤ 10μM
Z80561-1-O U2OS (Osteosarcoma Cells) (cluster #1 Of 1), Other Other 30 0.42 Functional ≤ 10μM
Z81117-1-O Keratinocytes (Keratinocytes) (cluster #1 Of 2), Other Other 8000 0.29 Functional ≤ 10μM
Z81135-4-O L6 (Skeletal Muscle Myoblast Cells) (cluster #4 Of 4), Other Other 5000 0.30 Functional ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
AOFB_HUMAN P27338 Monoamine Oxidase B, Human 832 0.34 Binding ≤ 1μM
PPARA_HUMAN Q07869 Peroxisome Proliferator-activated Receptor Alpha, Human 140 0.38 Binding ≤ 1μM
PPARG_HUMAN P37231 Peroxisome Proliferator-activated Receptor Gamma, Human 10 0.45 Binding ≤ 1μM
PPARG_RAT O88275 Peroxisome Proliferator-activated Receptor Gamma, Rat 325 0.36 Binding ≤ 1μM
RXRA_RAT Q05343 Retinoid X Receptor Alpha, Rat 325 0.36 Binding ≤ 1μM
AOFB_HUMAN P27338 Monoamine Oxidase B, Human 832 0.34 Binding ≤ 10μM
PPARA_HUMAN Q07869 Peroxisome Proliferator-activated Receptor Alpha, Human 140 0.38 Binding ≤ 10μM
PPARD_HUMAN Q03181 Peroxisome Proliferator-activated Receptor Delta, Human 3620 0.30 Binding ≤ 10μM
PPARG_HUMAN P37231 Peroxisome Proliferator-activated Receptor Gamma, Human 10 0.45 Binding ≤ 10μM
PPARG_RAT O88275 Peroxisome Proliferator-activated Receptor Gamma, Rat 325 0.36 Binding ≤ 10μM
RARG_HUMAN P13631 Retinoic Acid Receptor Gamma, Human 10000 0.28 Binding ≤ 10μM
RXRA_RAT Q05343 Retinoid X Receptor Alpha, Rat 325 0.36 Binding ≤ 10μM
Z80106 Z80106 COS-1 (Kidney Cells) 23 0.43 Functional ≤ 10μM
Z80169 Z80169 Huh-7 (Hepatocellular Carcinoma) 220 0.37 Functional ≤ 10μM
Z81117 Z81117 Keratinocytes (Keratinocytes) 8000 0.29 Functional ≤ 10μM
Z81135 Z81135 L6 (Skeletal Muscle Myoblast Cells) 5000 0.30 Functional ≤ 10μM
PPARA_HUMAN Q07869 Peroxisome Proliferator-activated Receptor Alpha, Human 10000 0.28 Functional ≤ 10μM
PPARG_MOUSE P37238 Peroxisome Proliferator-activated Receptor Gamma, Mouse 60 0.40 Functional ≤ 10μM
PPARG_HUMAN P37231 Peroxisome Proliferator-activated Receptor Gamma, Human 10 0.45 Functional ≤ 10μM
Z80561 Z80561 U2OS (Osteosarcoma Cells) 30 0.42 Functional ≤ 10μM

Direct Reactome Annotations (via ChEBI)

Description Species
Fatty Acids bound to GPR40 (FFAR1) regulate insulin secretion
Free fatty acid receptors
G alpha (q) signalling events
PPARA activates gene expression
Synthesis, secretion, and inactivation of Glucagon-like Peptide-1 (GLP-1)
Synthesis, secretion, and inactivation of Glucose-dependent Insulinotropic Polyp
Transcriptional Regulation of Adipocyte Differentiation in 3T3-L1 Pre-adipocytes
Transcriptional regulation of white adipocyte differentiation

Reactome Annotations from Targets (via Uniprot)

Description Species
Activation of gene expression by SREBF (SREBP)
BMAL1:CLOCK,NPAS2 activates circadian gene expression
Circadian Clock
Import of palmitoyl-CoA into the mitochondrial matrix
Monoamines are oxidized to aldehydes by MAOA and MAOB, producing NH3 and H2O2
Nuclear Receptor transcription pathway
PPARA activates gene expression
Regulation of lipid metabolism by Peroxisome proliferator-activated receptor alp
Regulation of pyruvate dehydrogenase (PDH) complex
REV-ERBA represses gene expression
RORA activates circadian gene expression
Transcriptional activation of mitochondrial biogenesis
Transcriptional regulation of white adipocyte differentiation
YAP1- and WWTR1 (TAZ)-stimulated gene expression

Analogs ( Draw Identity 99% 90% 80% 70% )