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==Application to drugs== The Hydrogen bond is relevant to drug design. According to [[Lipinski's rule of five]] the majority of orally active drugs have no more than five hydrogen bond donors and fewer than ten hydrogen bond acceptors. These interactions exist between [[nitrogen]]–[[hydrogen]] and [[oxygen]]–hydrogen centers.<ref name="Lipinski_2004">{{cite journal | author = Lipinski CA | title = Lead- and drug-like compounds: the rule-of-five revolution | journal = Drug Discovery Today: Technologies |date=December 2004 | volume = 1 | issue = 4 | pages = 337–341 | doi = 10.1016/j.ddtec.2004.11.007 | pmid = 24981612 }}</ref> Many drugs do not, however, obey these "rules".<ref>{{cite journal |doi=10.1007/s11306-014-0733-z |title=A 'rule of 0.5' for the metabolite-likeness of approved pharmaceutical drugs |year=2015 |last1=o′Hagan |first1=Steve |last2=Swainston |first2=Neil |last3=Handl |first3=Julia |last4=Kell |first4=Douglas B. |journal=Metabolomics |volume=11 |issue=2 |pages=323–339 |pmid=25750602 |pmc=4342520 }}</ref>
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