1-(5-methoxy-1H-indol-3-yl)-2-(3-methylpiperidin-1-yl)ethan-1-one

• ChemBase ID: 179871
• Molecular Formular: C17H22N2O2
• Molecular Mass: 286.36878
• Monoisotopic Mass: 286.16812795
• SMILES: c1(c2c([nH]c1)ccc(c2)OC)C(=O)CN1CC(CCC1)C
• Canonical SMILES: COc1ccc2c(c1)c(c[nH]2)C(=O)CN1CCCC(C1)C
• InChI: InChI=1S/C17H22N2O2/c1-12-4-3-7-19(10-12)11-17(20)15-9-18-16-6-5-13(21-2)8-14(15)16/h5-6,8-9,12,18H,3-4,7,10-11H2,1-2H3
• InChIKey: PFIOEEULSVWXAH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(5-methoxy-1H-indol-3-yl)-2-(3-methylpiperidin-1-yl)ethan-1-one
• IUPAC Traditional name: 1-(5-methoxy-1H-indol-3-yl)-2-(3-methylpiperidin-1-yl)ethan-1-one
• Synonyms: GR-128107

Database IDs

• PubChem SID: 164235781
• PubChem CID: 659176

CALCULATED PROPERTIES

• Acid pKa: 13.442018
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.6519049
• LogD (pH = 7.4): 2.26088
• Log P: 2.5788214
• Molar Refractivity: 84.0531 cm^3
• Polarizability: 33.659374 Å^3
• Polar Surface Area: 45.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Dopamine antagonist; Melatonin receptor antagonist

Product Information

• Application(s): Neuroleptic

REFERENCES

• 1. Dubocovich, M.L., Witt-Enderby, P.A., and Masana, M.I. Affinity and Efficacy of Agonists, Partial Agonists, and Antagonists for the Human mel1a Melatonin Receptor Subtype.
• The Pharmacologist, 39(1) : 68, 1997.
• 2. Teh MT, Sugden D. The putative melatonin receptor antagonist GR128107 is a partial agonist on Xenopus laevis melanophores. Br J Pharmacol. 1999 Mar;126(5):1237-45.