Lipinski's Rule of Five

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In 1997 Christopher A. Lipinski published a seminal paper identifying a series of features commonly found in orally active drugs. These features are referred to as Lipinski's rule of five and can be used as a rule of thumb to indicate whether a molecule is likely to be orally bioavailable (bioactive).The "rule of five" is so called because most of the features start with the number five.

  • Not more than 5 hydrogen bond donors (OH and NH groups)
  • Not more than 10 hydrogen bond acceptors (notably N and O)
  • Molecular weight under 500
  • LogP under 5
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