Non-covalent interactions involving halogenated derivatives of capecitabine and thymidylate synthase: a computational approach

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Table 5 Selected non-covalent interactions among drugs D1–D4 and TYMS obtained via flexible docking

Systems	Contacts	Bond type	Bond distances (Å)	Systems	Contacts	Bond Type	Bond distances (Å)
D1-TYMS	O–H–O Arg78	Hydrogen	2.43	D3-TYMS	O–H–N Lys77	Hydrogen	2.44
	O–H–N Phe80	Hydrogen	2.00		O–O Arg78	Donor	3.00
	alkyl–alkyl Ile108	Alkyl	4.21.5.26		C–H–O Arg78	Carbon	2.43
	alkyl-π Trp109	Alkyl-π	4.20,4.29		O–H-N Phe80	Hydrogen	2.90
	F–O Leu221	Halogen	2.82		Br–alkyl Ile108	Alkyl	5.09
	alkyl–alkyl Leu221	Alkyl	4.61,5.32		Alkyl-π Trp109	Alkyl-π	3.83, 4.81
	F–H–C Gly222	Carbon	3.26		N–H–O Leu221	Hydrogen	2.67
	F–C–π Phe225	Alkyl-π	4.54		O–H–C Gly222	Carbon	2.58
	C–C–S Met309	Alkyl	4.79		π–π Phe225	π stack	5.41
					O–H–O Ile307	Hydrogen	2.53
					C–H–O Ile307	Carbon	2.79
D2-TYMS	O–H–N Lys77	Hydrogen	2.21	D4-TYMS	O–H–N Lys77	hydrogen	2.48
	O–O Arg78	Donor	2.92		C–H–O Arg78	Carbon	2.35
	C-H–O Arg78	Carbon	2.46		O–H–N Phe80	Hydrogen	2.93
	O–H–N Phe80	Hydrogen	2.80		I-alkyl Ile108	Alkyl	5.18
	C–H–π Phe80	Alkyl- π	5.05		C–H–π Trp109	Alkyl-π	2.42, 4.33
	Alkyl–alkyl Ile108	Alkyl	4.77		Alkyl–alkyl	Alkyl	5.09
	C–H–π Trp109	Alkyl- π	2.52, 4.35		Leu221	carbon	2.54
	Cl–O Leu221	Halogen	2.00		C–H–O Gly222	π stack	5.42
	O–H–C Gly222	Carbon	2.60		π–π Phe225	Hydrogen	2.18, 1.97
	π–π Phe225	π stack	5.16		O–H–O Ile307
	O–H–O Ile307	Hydrogen	2.18, 2.34