Table 6. The molecular interactions between the compounds and AKR1B10 protein.

Compound	Hydrogen bond interaction				Hydrophobic interaction
	Ligand atom	Amino acid	Amino acid atom	Length (Å)
Inhibitora	O23	Lys22	HZ3	2.336	Val48, Gln50, His111, Trp112, Phe123, Cys299, Val301, Leu302
	O24	Tyr49	OH	2.446
	O24	Lys78	HZ2	1.939
Hit 1	O28	Lys22	HZ3	2.317	Val48, Trp80, His111, Trp112, Phe123, Asn161, Pro219, Trp220, Cys299, Val301, Leu302
	O28	Gln50	HE21	2.051
	H50	Tyr49	O	2.330
	O27	Lys125	HZ1	1.988
Hit 2	H44	Tyr49	OH	2.442	Trp21, Ala46, Val48, Lys78, Trp80, His111, Trp112, Phe123, Asn161, Trp220, Leu302
	O11	Cys299	HG	2.021
	O11	Val301	HN	2.494
Hit 3	O23	Lys22	HZ2	2.482	Trp21, Tyr49, Trp80, Trp112, Phe123, Pro219, Trp220, Val301, Leu302
	H42	Val48	O	1.474
	HE21	Gln50	O24	2.051
	H32	His111	NE2	1.676

^a Reference inhibitor; the most active compound in the training set, 7-hydroxy-2-(4-methoxyphenylimino)-2H-chromene-3-carboxylic acid benzylamide.