3-(4-{[(3-phenoxyphenyl)methyl]amino}phenyl)propanoic acid

• ChemBase编号: 154499
• 分子式: C22H21NO3
• 平均质量: 347.40704
• 单一同位素质量: 347.15214354
• SMILES: c1ccc(cc1)Oc1cccc(c1)CNc1ccc(cc1)CCC(=O)O
• Canonical SMILES: OC(=O)CCc1ccc(cc1)NCc1cccc(c1)Oc1ccccc1
• 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)
• InChIKey: DGENZVKCTGIDRZ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-(4-{[(3-phenoxyphenyl)methyl]amino}phenyl)propanoic acid
• IUPAC传统名: 3-(4-{[(3-phenoxyphenyl)methyl]amino}phenyl)propanoic acid
• 别名: 4-(3-Phenoxybenzylamino)phenylpropionic acid; GW9508; GW9508

登记号

• CAS号: 885101-89-3
• MDL号: MFCD09753282
• PubChem SID: 162248638
• PubChem CID: 11595431

理论计算性质

• Acid pKa: 3.4841511
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 3.7766879
• LogD (pH = 7.4): 2.070081
• Log P: 4.223595
• 摩尔折射率: 103.0138 cm^3
• 极化性: 39.26977 Å^3
• 极化表面积: 58.56 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: >20 mg/mL
• 外观: white powder

安全信息

• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 3077
• 德国WGK号: 3
• 联合国危险货物等级: 9
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 22-37/38-41-50/53
• 安全公开号: 26-39-60-61
• GHS危险品标识: GHS05; GHS07; GHS09
• GHS警示词: Danger
• GHS危险声明: H302-H315-H318-H335-H410
• GHS警示性声明: P261-P273-P280-P305 + P351 + P338-P501
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• 保存温度: 2-8°C

药理学性质

• 作用靶点: GPR

产品相关信息

• 纯度: ≥98% (HPLC)
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C22H21NO3

详细说明

Sigma Aldrich - G9797

Biochem/physiol Actions
GW9508 is a selective FFA1/GPR40 agonist. GPR40 was formerly an orphan G protein-coupled receptor whose endogenous ligands have now been identified as free fatty acids (FFAs). The receptor, named FFA receptor 1, has been implicated in the pathophysiology of type 2 diabetes and is a drug target because of its role in FFA-mediated enhancement of glucose-stimulated insulin release. GW9508 showed greater than 500-fold selectivity for GPR40 over GPR41 and GPR43 and possessed a good in vitro and in vivo profile with excellent bioavailability. GW9508 stimulated intracellular Ca2+ mobilization in human embryonic kidney HEK-293 cells expressing GPR40 or GPR120, but not in the parent HEK-293 cell line. GW9508 dose dependently potentiated glucose-stimulated insulin secretion in MIN6 cells, but not in primary rat or mouse islets. GW9508 potentiates the KCl-mediated increase in insulin secretion in MIN6 cells.