3-[2-(2-chloro-4-{[3-(2,6-dichlorophenyl)-5-(propan-2-yl)-1,2-oxazol-4-yl]methoxy}phenyl)ethenyl]benzoic acid

• ChemBase ID: 154436
• Molecular Formular: C28H22Cl3NO4
• Molecular Mass: 542.83758
• Monoisotopic Mass: 541.06144123
• SMILES: CC(C)c1c(c(no1)c1c(cccc1Cl)Cl)COc1ccc(c(c1)Cl)/C=C/c1cccc(c1)C(=O)O
• Canonical SMILES: Clc1cc(ccc1/C=C/c1cccc(c1)C(=O)O)OCc1c(onc1c1c(Cl)cccc1Cl)C(C)C
• InChI: InChI=1S/C28H22Cl3NO4/c1-16(2)27-21(26(32-36-27)25-22(29)7-4-8-23(25)30)15-35-20-12-11-18(24(31)14-20)10-9-17-5-3-6-19(13-17)28(33)34/h3-14,16H,15H2,1-2H3,(H,33,34)
• InChIKey: BYTNEISLBIENSA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[2-(2-chloro-4-{[3-(2,6-dichlorophenyl)-5-(propan-2-yl)-1,2-oxazol-4-yl]methoxy}phenyl)ethenyl]benzoic acid; 3-[(E)-2-(2-chloro-4-{[3-(2,6-dichlorophenyl)-5-(propan-2-yl)-1,2-oxazol-4-yl]methoxy}phenyl)ethenyl]benzoic acid
• IUPAC Traditional name: 3-[2-(2-chloro-4-{[3-(2,6-dichlorophenyl)-5-isopropyl-1,2-oxazol-4-yl]methoxy}phenyl)ethenyl]benzoic acid; 3-[(E)-2-(2-chloro-4-{[3-(2,6-dichlorophenyl)-5-isopropyl-1,2-oxazol-4-yl]methoxy}phenyl)ethenyl]benzoic acid
• Synonyms: 3-(2,6-Dichlorophenyl)-4-(3’-carboxy-2-chlorostilben-4-yl)oxymethyl-5-isopropylisoxazole; GW4064; 3-[2-[2-Chloro-4-[[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methoxy]phenyl]ethenyl]-benzoic Acid; GW 4064

Database IDs

• CAS Number: 278779-30-9
• MDL Number: MFCD09971006
• PubChem SID: 162248575
• PubChem CID: 9893571

CALCULATED PROPERTIES

• Acid pKa: 4.0139914
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 7.33821
• LogD (pH = 7.4): 5.683282
• Log P: 8.834283
• Molar Refractivity: 144.6107 cm^3
• Polarizability: 55.96626 Å^3
• Polar Surface Area: 72.56 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: white powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319-H413
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: FXR

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C28H22Cl3NO4

DETAILS

Sigma Aldrich - G5172

Biochem/physiol Actions
GW4064 is a FXR agonist. GW4064 is a potent (EC50 = 15 nM), non-steroidal agonist of the orphan nuclear receptor FXR. It shows no activity on other nuclear receptors including RAR up to 1 mM. This is an important tool for the study of the involvment of FXR in a variety of biological activities.

Toronto Research Chemicals - G931000

A novel nonsteroidal FXR nuclear receptor agonist.

REFERENCES

• Makishima, M., et al.: Science, 284, 1362 (1999)
• Wang, H., et al.: Mol. Cell, 3, 543 (1999)
• Zhang, Y., et al.: J. Biol. Chem., 276, 43018 (1999)
• Carlton, V.E., et al.: Nat. Genet., 34, 91 (1999)