title: Sweetness prediction of natural compounds.
abstract: Based on the most exhaustive database of sweeteners with known sweetness values, a new quantitative structure-activity relationship model for sweetness prediction has been set up. Analysis of the physico-chemical properties of sweeteners in the database indicates that the structure of most potent sweeteners combines a hydrophobic scaffold functionalized by a limited number of hydrogen bond sites (less than 4 hydrogen bond donors and 10 acceptors), with a moderate molecular weight ranging from 350 to 450g·mol-1. Prediction of sweetness, bitterness and toxicity properties of the largest database of natural compounds have been performed. In silico screening reveals that the majority of the predicted natural intense sweeteners comprise saponin or stevioside scaffolds. The model highlights that their sweetness potency is comparable to known natural sweeteners. The identified compounds provide a rational basis to initiate the design and chemosensory analysis of new low-calorie sweeteners.
authors.affiliation: Université Côte d'azur, CNRS, Institut de Chimie de Nice UMR7272, 06108 Nice, France.
authors.forename: Jean-Baptiste
authors.initials: JB
authors.lastname: Chéron
authors.affiliation: Université Côte d'azur, CNRS, Institut de Chimie de Nice UMR7272, 06108 Nice, France.
authors.forename: Iuri
authors.initials: I
authors.lastname: Casciuc
authors.affiliation: Université Côte d'azur, CNRS, Institut de Chimie de Nice UMR7272, 06108 Nice, France.
authors.forename: Jérôme
authors.initials: J
authors.lastname: Golebiowski
authors.affiliation: Université Côte d'azur, CNRS, Institut de Chimie de Nice UMR7272, 06108 Nice, France.
authors.forename: Serge
authors.initials: S
authors.lastname: Antonczak
authors.affiliation: Université Côte d'azur, CNRS, Institut de Chimie de Nice UMR7272, 06108 Nice, France. Electronic address: sebastien.fiorucci@unice.fr.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Fiorucci
mesh_terms: D001688:Biological Products; D006801:Humans; D013329:Structure-Activity Relationship; D013549:Sweetening Agents / Q000737:chemistry*
chemical_list: D001688:Biological Products; D013549:Sweetening Agents
keywords: Chemical space; Natural compounds; Structure-activity relationship; Sweeteners