Table 3. Galectin-3 Affinity, Permeability, Polar Surface Area, and Lipophilicity Determined for α-d-Monogalactopyranosides 11a–d^a.

compound	R	galectin-3 (μM)a	CACO-2 (A > B/B > A) Papp (10–6 cm/s)b	PSA (Å2)c	log D (pH 7.4)d	LiPEe
11a	4-acetamidophenyl	0.38 ± 0.030	0.5/13	130	2.28	4.1
11b	3,4-dichlorophenyl	0.037 ± 0.0010	14/16	101	4.6	2.8
11c	3-chloro-4-cyanophenyl	0.047 ± 0.0063	5/32	124	3.7	3.6
11d	5-bromo-3-pyridyl	0.025 ± 0.0017	4.6/30	114	3.0	4.6

^aK_d was determined by fluorescence polarization.^14,32

^bPermeability (Papp) was determined as permeability over CACO-2 cells from the apical (A) to basolateral side (B) and vice versa.³⁵

^cPolar surface area was calculated according to Ertl²⁹ within the database solution LiveDesign, Schrodinger.

^dLog D was determined by measuring the distribution of compound between 10 mM potassium phosphate buffer (pH 7.4) and octanol using a standard shakeflask method.

^eLipophilic efficiency was calculated as LipE = pK_d – log D (pH 7.4).