4-[5-(4-butylcyclohexyl)-1,2,4-oxadiazol-3-yl]pyridine

• ChemBase ID: 129169
• Molecular Formular: C17H23N3O
• Molecular Mass: 285.38402
• Monoisotopic Mass: 285.18411237
• SMILES: C1CC(CCCC)CCC1c1onc(n1)c1ccncc1
• Canonical SMILES: CCCCC1CCC(CC1)c1onc(n1)c1ccncc1
• InChI: InChI=1S/C17H23N3O/c1-2-3-4-13-5-7-15(8-6-13)17-19-16(20-21-17)14-9-11-18-12-10-14/h9-13,15H,2-8H2,1H3
• InChIKey: OAVLEYPTWABFLF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[5-(4-butylcyclohexyl)-1,2,4-oxadiazol-3-yl]pyridine
• IUPAC Traditional name: 4-[5-(4-butylcyclohexyl)-1,2,4-oxadiazol-3-yl]pyridine
• Synonyms: PSN-375,963; 4-[5-(4-butylcyclohexyl)-1,2,4-oxadiazol-3-yl]-pyridine; PSN-375963

Database IDs

• CAS Number: 388575-52-8
• MDL Number: MFCD01829706
• PubChem SID: 162223466
• PubChem CID: 2875918
• Wikipedia Title: PSN-375,963

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.667191
• LogD (pH = 7.4): 4.667768
• Log P: 4.667775
• Molar Refractivity: 93.9228 cm^3
• Polarizability: 32.427986 Å^3
• Polar Surface Area: 51.81 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white powder

Safety Information

• German water hazard class: nwg
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H23N3O

DETAILS

Sigma Aldrich - P0028

Biochem/physiol Actions
PSN-375963 is a GPR119 partial agonist. GPR119 is an orphan GPCR, expressed predominantly in pancreas and GI tract, that has been characterized. Its endogenous ligands are oleoylethanolamide (OEA) and oleoyl-lysophosphatidylcholine, lipid signaling molecules that regulate food intake and body weight. OEA decreases food intake, so GPR119 agonists are potential therapies for obesity. Initial studies showed that PSN-375963 has similar potency and partial efficacy compared to OEA. Further studies revealed that although OEA and PSN-375963 are GPR119 agonists, they have divergent effects on insulin secretion, calcium signaling, and cAMP production.