1-(4-{3-[4-(2,3-dimethylphenyl)piperazin-1-yl]-2-hydroxypropoxy}phenyl)ethan-1-one

• ChemBase ID: 155049
• Molecular Formular: C23H30N2O3
• Molecular Mass: 382.4959
• Monoisotopic Mass: 382.22564283
• SMILES: Cc1cccc(c1C)N1CCN(CC1)CC(COc1ccc(cc1)C(=O)C)O
• Canonical SMILES: OC(CN1CCN(CC1)c1cccc(c1C)C)COc1ccc(cc1)C(=O)C
• InChI: InChI=1S/C23H30N2O3/c1-17-5-4-6-23(18(17)2)25-13-11-24(12-14-25)15-21(27)16-28-22-9-7-20(8-10-22)19(3)26/h4-10,21,27H,11-16H2,1-3H3
• InChIKey: KQZDGQRWGREOJP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-{3-[4-(2,3-dimethylphenyl)piperazin-1-yl]-2-hydroxypropoxy}phenyl)ethan-1-one
• IUPAC Traditional name: 1-(4-{3-[4-(2,3-dimethylphenyl)piperazin-1-yl]-2-hydroxypropoxy}phenyl)ethanone
• Synonyms: 1-[4-[3-[4-(2,3-dimethylphenyl)-1-piperazinyl]-2-hydroxypropoxy]phenyl]-ethanone; GPV574

Database IDs

• CAS Number: 635703-12-7
• MDL Number: MFCD20527325
• PubChem SID: 162249187
• PubChem CID: 44421046

CALCULATED PROPERTIES

• Acid pKa: 14.07615
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.2086024
• LogD (pH = 7.4): 3.4294314
• Log P: 3.5266142
• Molar Refractivity: 113.5366 cm^3
• Polarizability: 43.31265 Å^3
• Polar Surface Area: 53.01 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL (warmed to 60°C)
• Apperance: white to tan powder

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H30N2O3

DETAILS

Sigma Aldrich - SML0135

Biochem/physiol Actions
GPV574 is a derivative of the Class 1C antiarrhythmic drug propafenone. GPV574 inhibits the delayed rectifier K+ channel HERG with similar affinity and time constant as propafenone (IC50 = 5 mM), but unlike the parent compound, does not remain permanently trapped in the channel pore. After wash-out of GPV574, channel activity is recovered within 60 seconds.