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

• ChemBase ID: 154499
• Molecular Formular: C22H21NO3
• Molecular Mass: 347.40704
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-{[(3-phenoxyphenyl)methyl]amino}phenyl)propanoic acid
• IUPAC Traditional name: 3-(4-{[(3-phenoxyphenyl)methyl]amino}phenyl)propanoic acid
• Synonyms: 4-(3-Phenoxybenzylamino)phenylpropionic acid; GW9508; GW9508

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 3.4841511
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.7766879
• LogD (pH = 7.4): 2.070081
• Log P: 4.223595
• Molar Refractivity: 103.0138 cm^3
• Polarizability: 39.26977 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white powder

Safety Information

• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 22-37/38-41-50/53
• Safety Statements: 26-39-60-61
• GHS Pictograms: GHS05; GHS07; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H318-H335-H410
• GHS Precautionary statements: P261-P273-P280-P305 + P351 + P338-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: GPR

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C22H21NO3

DETAILS

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.