Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings

Scales of solute hydrogen-bonding: their construction and application to physicochemical and biochemical processes

https://onlinelibrary.wiley.com/doi/pdf/10.1002/jps.2600830806

Hydrogen bonding. 32. An analysis of water-octanol and water-alkane partitioning and the Δlog p parameter of seiler

Matrix metalloproteinases (MMPs): Chemical–biological functions and (Q)SARs

The van der Waals volume is a widely used descriptor in modeling physicochemical properties. However, the calculation of the van der Waals volume (VvdW) is rather time-consuming, from Bondi group contributions, for a large data set. A new method for calculating van der Waals volume has been developed, based on Bondi radii. The method, termed Atomic and Bond Contributions of van der Waals volume (VABC), is very simple and fast. The only information needed for calculating VABC is atomic contributions and the number of atoms, bonds, and rings. Then, the van der Waals volume (A3/molecule) can be calculated from the following formula:  VvdW = ∑ all atom  contributions − 5.92NB − 14.7RA − 3.8RNR (NB is the number of bonds, RA is the number of aromatic rings, and RNA is the number of nonaromatic rings). The number of bonds present (NB) can be simply calculated by NB = N − 1 + RA + RNA (where N is the total number of atoms). A simple Excel spread sheet has been made to calculate van der Waals volumes for a wide r...

Fast Calculation of van der Waals Volume as a Sum of Atomic and Bond Contributions and Its Application to Drug Compounds

In the correlation of reversed-phase liquid chromatography capacity factors through the equation,
 
$$\log k' = log k'_0 + mV/100 + s\pi _2^* + b\beta _2 + a\alpha _2 $$

 the use of McGowans characteristic volume, Vx, which can be trivially calculated, is entirely equivalent to the use of Leahy's computer-calculated intrinsic volumes, V1, for the cavity term mV/100. It is shown that for 209 gaseous, liquid, and solid solutes, the two sets of volumes are related through the equation,
 
$$V_1 = 0.597 + 0.6823 V_x $$

 with a standard deviation of only 1.24cm3 mol−1, and a correlation coefficient of 0.9988.

J. C. McGowan

Papers

The use of characteristic volumes to measure cavity terms in reversed phase liquid chromatography