Table 3. Intermolecular interactions between ACE inhibitors and the tACE binding site.

		LISINOPRIL	ENALAPRILAT	CAPTOPRIL	RXPA380	SELENOCAPTOPRIL	KAF	KAW	lisW-S	FII-A	LUTEOLIN	QUERCETIN	RUTIN	KAEMPFEROL
S2′	Gln281	✓	✓	NE2	NE2	NE2	NE2	✓	H	H
	Thr282										✓	✓	✓	✓
	His353	NE2	NE2	NE2	NE2	NE2	NE2	NE2	NE2	NE2	✓	✓	✓	✓
	Glu376									✓			✓
	Asp453													✓
	Lys511	NZ	NZ	NZ	NZ	NZ	NZ	NZ	NZ	NZ
	His513	NE2	NE2	NE2	NE2	NE2	NE2	NE2	NE2	NE2
	Tyr520	OH	OH	OH	OH	OH	OH	OH	OH	OH
S2′/S1′	Ser284
	Val379										✓	✓	✓	✓
	Val380	✓							✓	✓	✓		✓	✓
S1′	Glu162	✓											OE2
	Asn277												✓
	Asn374
	Asp377												OD1
S1	Glu143
	Val351
	Ala354	O	O	✓	✓	✓	✓	✓	O	✓	✓	✓	O	O
	Ser355		✓		✓		✓	✓		✓	✓	✓	✓
	Trp357
	Lys368
	Glu384	OE2	OE2	OE2	OE2	✓	OE2	OE2	OE2	OE2	✓	✓	✓
	Phe512	✓	✓		✓		✓	✓	✓	✓
	Ser516
	Tyr523	OH	OH	✓	OH	✓	OH	OH	OH	OH	OH	OH	OH	✓
S1/S2	Val518	✓	✓		✓		✓	✓	✓	✓
S2	Phe391				✓		✓	✓		✓
	Glu403
	Arg522
Other	Thr166												✓
	Trp279												✓
	Ala356				N		N	N		N
	His383	✓	✓	✓	NE2	✓	NE2	NE2	NE2	NE2				✓
	His387	NE2	✓	✓	NE2		✓	✓	NE2	NE2
	His410				✓		✓			✓
	Glu411	✓	✓		✓		OE1	✓	✓				OE1
	Asp415				✓			✓	OD2		✓	OD1	✓	✓
	Lys454												NZ	NZ
	Phe457	✓	✓	✓	✓	✓	✓	✓	✓	✓
	Phe527								✓	✓			✓

Data used for lisinopril, enalaprilat, captopril, RXPA380, selenocaptopril, KAF, KAW, lisW-S and FII-A was obtained from the LigPlot+ diagrams that are available at the PDBsum resource (http://www.ebi.ac.uk/pdbsum/) for PDB files 1O86, 1UZE, 1UZF, 2OC2, 2YDM, 3BKK, 3BKL, 3L3N and 2XY9, respectively. Data for luteolin, quercetin, rutin and kaempferol was obtained by applying LigPlot+ to the structure of their predicted complexes with tACE. Hydrophobic contacts are indicated by a check mark whereas hydrogen bonds are indicated with the label of the protein atom that is involved.