Rule of five

{
  "id": "MLC-T-CHM-010452",
  "term": "Rule of five",
  "field": "Chemistry",
  "definition": "A set of four property limits, formulated by Christopher Lipinski, used to flag compounds likely to have poor oral absorption or membrane permeation: more than 5 hydrogen bond donors, more than 10 hydrogen bond acceptors (counted as nitrogen and oxygen atoms), molecular weight above 500, and calculated log P above 5. Compounds that break two or more of these limits are the ones predicted to have problems. Natural products, peptides and substrates of biological transporters are known exceptions.",
  "subject": "Chemistry and Human Health",
  "see_also": [
    "log P"
  ],
  "references": [
    "PAC, 2016, 88, 239. 'Glossary of terms used in computational drug design, part II (IUPAC Recommendations 2015)' on page 255 (https://doi.org/10.1515/pac-2012-1204)"
  ],
  "url": "https://mlchart.com/terminology/chemistry/rule-of-five/"
}