5-(4-chlorophenyl)-3-phenylpent-2-enoic acid

• ChemBase ID: 154745
• Molecular Formular: C17H15ClO2
• Molecular Mass: 286.7528
• Monoisotopic Mass: 286.0760574
• SMILES: c1ccc(cc1)/C(=C\C(=O)O)/CCc1ccc(cc1)Cl
• Canonical SMILES: OC(=O)/C=C(\c1ccccc1)/CCc1ccc(cc1)Cl
• InChI: InChI=1S/C17H15ClO2/c18-16-10-7-13(8-11-16)6-9-15(12-17(19)20)14-4-2-1-3-5-14/h1-5,7-8,10-12H,6,9H2,(H,19,20)
• InChIKey: LLJYFDRQFPQGNY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(4-chlorophenyl)-3-phenylpent-2-enoic acid
• IUPAC Traditional name: 5-(4-chlorophenyl)-3-phenylpent-2-enoic acid
• Synonyms: 5-(4-Chloro-phenyl)-3-phenyl-pent-2-enoic acid; PS48

Database IDs

• CAS Number: 1180676-32-7
• MDL Number: MFCD17215962
• PubChem SID: 162248883
• PubChem CID: 44141940

CALCULATED PROPERTIES

• Acid pKa: 4.59182
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.1047344
• LogD (pH = 7.4): 2.329152
• Log P: 5.0624666
• Molar Refractivity: 81.4437 cm^3
• Polarizability: 31.249666 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: protect from light
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H15ClO2

DETAILS

Sigma Aldrich - P0022

Biochem/physiol Actions
PS48 is a PDK1 (phosphoinositide-dependent protein kinase 1) activator which binds to the HM/PIF binding pocket rather than the ATP-binding site. PS48 is one of only a few truly allosteric compounds targeting a regulatory binding site on a protein kinase catalytic domain that is not adjacent to or overlapping with the ATP-binding site.