| Chemical & Physical Properties | |
|---|---|
| CAS Number | 885101-89-3 |
| Catalog No. | 2A-0127268 |
| Chinese Name | 4-[[(3-苯氧苯基)甲基]氨基]苯乙酸 |
| Synonyms | 3-{4-[(3-Phenoxybenzyl)amino]phenyl}propanoic acid; gw9508; GW-9508 |
| Molecular Formula | C22H21NO3 |
| Molecular Weight | 347.41 |
| Purity | 96+ |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 538.4±45.0 °C at 760 mmHg |
| Water Solubility | DMSO: >20mg/mL |
| Storage Condition | Store at RT |
| Application | GW9508 is an FFA1 (GPR40) agonist with a pEC50 of 7.32, which is 100 times more inhibitory than GPR120. It can stimulate insulin secretion in a glucose-sensitive manner. |
| EINECS | 0 |
| HTC | 0 |
| UN(IATA) | 0 |
| PubChem ID | 329799992 |
| MDL Number | MFCD09753282 |
| SMILES | O=C(O)CCc1ccc(NCc2cccc(Oc3ccccc3)c2)cc1 |
| InChI | InChI=1S/C22H21NO3/c24-22(25)14-11-17-9-12-19(13-10-17)23-16-18-5-4-8-21(15-18)26-20-6-2-1-3-7-20/h1-10,12-13,15,23H,11,14,16H2,(H,24,25) |
| InChI Key | DGENZVKCTGIDRZ-UHFFFAOYSA-N |
| NACRES Code | NA.25 |
| UNSPSC | 51111800 |
| Hazard Symbols | transportation |
| Bioactivity | GW9508 is a potent and selective agonist for FFA1 (GPR40) with pEC50 of 7.32, 100-fold selective against GPR120, stimulates insulin secretion in a glucose-sensitive manner.IC50 value: 7.32 (pEC50) [1]Target: GPR40GW9508 is shown to be at least 100-fold selective against 220 other GPCRs, 60 kinases, 63 proteases, seven integrins and 20 nuclear receptors including PPARα, δ and γ (pEC50 4.0, 4 and 4.9, respectively). GW9508 produces a concentration-dependent increase in intracellular Ca2+ concentrations via GPR40 receptor activation and the GPR120 receptor. GW9508 is active as an agonist at both GPR40 and GPR120, it is approximately 100-fold selective for GPR40 with respect to GPR120. GW9508 produces a concentration-dependent increase (pEC50=6.14) in glucose-stimulated insulin secretion at high glucose levels (25 mM). GW9508 dose dependently stimulated insulin secretion in a glucose-sensitive manner in MIN6 cells. Furthermore, GW9508 is able to potentiate the KCl-mediated increase in insulin secretion in MIN6 cells. [1] GW9508 induced hyperpolarization and opening of KATP channels in rat β-cells. [2] GW9508 inhibits CCL17 and CCL5 expression in a pertussis toxin-sensitive manner. GW9508 further suppresses expression of IL-11, IL-24, and IL-33 induced in HaCaT cells by TNF-α and IFN-γ. GW9508 also inhibits CCL5 and CXCL10 production by normal human epidermal keratinocytes. [3] Related Catalog Signaling Pathways >> GPCR/G Protein >> GPR40 Research Areas >> Metabolic Disease References [1]. Briscoe CP, et al. Pharmacological regulation of insulin secretion in MIN6 cells through the fatty acid receptor GPR40: identification of agonist and antagonist small molecules. Br J Pharmacol. 2006 Jul;148(5):619-28. [2]. Zhao YF, et al. Activation of ATP-sensitive potassium channels in rat pancreatic beta-cells by linoleic acid through both intracellular metabolites and membrane receptor signalling pathway. J Endocrinol, 2008, 198(3), 533-540. [3]. Fujita T, et al. A GPR40 agonist GW9508 suppresses CCL5, CCL17, and CXCL10 induction in keratinocytes and attenuates cutaneous immune inflammation. J Invest Dermatol, 2011, 131(8), 1660-1667. Chemical & Physical Properties Density 1.2±0.1 g/cm3 Boiling Point 538.4±45.0 °C at 760 mmHg Molecular Formula C22H21NO3 Molecular Weight 347.407 Flash Point 279.4±28.7 °C Exact Mass 347.152130 PSA 58.56000 LogP 4.74 Vapour Pressure 0.0±1.5 mmHg at 25°C Index of Refraction 1.641 InChIKey DGENZVKCTGIDRZ-UHFFFAOYSA-N SMILES O=C(O)CCc1ccc(NCc2cccc(Oc3ccccc3)c2)cc1 Storage condition Store at RT Water Solubility DMSO: >20mg/mL |
| Use of | Properties Articles11 Name 3-[4-[(3-phenoxyphenyl)methylamino]phenyl]propanoic acid Synonym More Synonyms GW9508 Biological Activity Related Catalog Signaling Pathways >> GPCR/G Protein >> GPR40 Research Areas >> Metabolic Disease References [2]. Zhao YF, et al. Activation of ATP-sensitive potassium channels in rat pancreatic beta-cells by linoleic acid through both intracellular metabolites and membrane receptor signalling pathway. J Endocrinol, 2008, 198(3), 533-540. [3]. Fujita T, et al. A GPR40 agonist GW9508 suppresses CCL5, CCL17, and CXCL10 induction in keratinocytes and attenuates cutaneous immune inflammation. J Invest Dermatol, 2011, 131(8), 1660-1667. Chemical & Physical Properties Molecular Formula C22H21NO3 Exact Mass 347.152130 PSA 58.56000 Index of Refraction 1.641 InChIKey DGENZVKCTGIDRZ-UHFFFAOYSA-N Storage condition Store at RT |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN number European Land Transport Danger Regulations: 3077 International Maritime Transport Danger Regulations: 3077 International Air Transport Danger Regulations: 3077 14.2 Names specified by the United Nations (UN) European land transport hazard regulations: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (4-(3- Phenoxybenzylamino)phenylpropionic acid) IMDG: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (4-(3- Phenoxybenzylamino)phenylpropionic acid) International air transport hazard regulations: Environmentally hazardous substance, solid, n.o.s. (4-(3- Phenoxybenzylamino)phenylpropionic acid) 14.3 Transport hazard categories European land transport Dangerous Regulations: 9 International sea transport Dangerous Regulations: 9 International air transport Dangerous Regulations: 9 14.4 Package group European Land Transport Danger Regulations: III International Maritime Transport Danger Regulations: III International Air Transport Danger Regulations: III 14.5 Environmental hazards European Land Transport Dangerous Regulations: Yes International Maritime Transport Dangerous Regulations Maritime Pollutants: Yes International Air Transport Dangerous Regulations: Yes 14.6 Special reminder to users further information Dangerous goods are individually packaged, with liquids exceeding 5 liters or solids exceeding 5 kilograms. The outer packaging of each independent package and the combined independent inner package must have EHS on it. Identification (according to European ADR Regulation 2.2.9.1.10, IMDG Regulation 2.10.3), |
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