Comparison of aqueous solubility estimation from AQUAFAC and the GSE

Jain, Parijat; Sepassi, Kia; Yalkowsky, Samuel H.

doi:10.1016/j.ijpharm.2008.04.028

Cited by 18 publications

(8 citation statements)

References 11 publications

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“…A similar phenomenon, whereby compounds are repellents when offered alone and neutral or attractive in a mixture, was recently described in insects [34]. The occurrence of 1-hexen-3-one, but not 3-hexanone, in C. visseri nectar (electronic supplementary material, table S1) is an intriguing feature of this system, as both compounds are soluble in water [35], so their contrasting presence in nectar suggests different secretion processes. Although 1-hexen-3-one was repellent to naive mice when offered alone, it may still function as an honest advertisement of the nectar reward [22].…”

Section: Discussionsupporting

confidence: 60%

Mammal pollinators lured by the scent of a parasitic plant

et al. 2011

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To communicate with animals, plants use signals that are distinct from their surroundings. Animals generally learn to use these signals through associative conditioning; however, signals are most effective when they elicit innate behavioural responses. Many plant species have flowers specialized for pollination by ground-dwelling mammals, but the signals used to attract these pollinators have not been elucidated. Here, we demonstrate the chemical basis for attraction of mammal pollinators to flowers of the dioecious parasitic plant Cytinus visseri (Cytinaceae). Two aliphatic ketones dominate the scent of this species; 3-hexanone, which elicits strong innate attraction in rodents, and 1-hexen-3-one, which repels them in isolation, but not in combination with 3-hexanone. The aliphatic ketone-dominated scent of C. visseri contrasts with those of insect-pollinated plants, which are typically dominated by terpenoids, aromatic or non-ketone aliphatic compounds. 3-hexanone is also known from some bat-pollinated species, suggesting independent evolution of plant signals in derived, highly specialized mammal-pollination systems.

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Section: Discussionsupporting

confidence: 60%

Mammal pollinators lured by the scent of a parasitic plant

et al. 2011

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“…In general, there is an inverse relationship between solubility and partition coefficient, especially for liquid solutes. Hansch et al [5] showed that for a large number of organic liquids, the aqueous solubility can be accurately predicted based on log K ow alone, by B K A S ow + = log log (2) where A and B are constants that depend on the data set considered.…”

Section: Resultsmentioning

confidence: 99%

“…However, the model is only applicable to non-ionized organic compounds and the experimental melting point of the free acid or free base is not always available. Jain et al [2] have shown that the GSE, which is semi-empirically derived from thermodynamic principles, provides reasonably accurate solubility predictions (Average absolute error, AAE, 0.576) for 1642 compounds.…”

Section: Introductionmentioning

confidence: 99%

Predicting Aqueous Solubility: The Role of Crystallinity

Chu¹,

Yalkowsky²

2009

CDM

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This paper revisits the role of crystallinity in predicting the aqueous solubility of a wide variety of organic compounds. Box and Comer (Current Drug Metabolism, 2008, 9, 869-878) fitted solubility data for 86 drugs to an equation based solely on log P. The General Solubility Equation of Jain and Yalkowsky, which accounts for the crystal lattice energy, was applied to the same data set and gives more accurate solubility predictions. In this simple comparison between two solubility prediction methods, we show that log P alone is only half of the solution, and that there is a need to include the melting point when dealing with crystalline solutes.

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“…The two parameters, logP and mp are good representatives of effects of hydrophobicity and crystal packing on the solubility of a certain solute. Jain et al (2008) provided some theoretical background for general single equation from thermodynamic principles. The simplicity of the model is its main advantage and a possible disadvantage is the melting point as an experimental parameter which may not be available for some of the compounds in early stages of drug discovery.…”

Section: Aqueous Solubilitymentioning

confidence: 99%