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Lipinski rule of five template

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Aspirin, ibuprofen, atorvastatin and cyclosporine with a table of MW, RDKit Crippen cLogP, H-bond donors (OH + NH) and acceptors (N + O) and the number of rule-of-five violations, all computed in RDKit.

What the template shows

MW ≤ 500, cLogP ≤ 5, ≤ 5 H-bond donors, ≤ 10 acceptors: worked on four drugs
The four drugs
analgesic · 0 violations
NSAID (racemate) · 0 violations
statin · 2 violations (MW, cLogP); oral F ≈ 14%
cyclic peptide immunosuppressant · 2 violations (MW, N + O)
Rule-of-five table (computed in RDKit)
ᵃ RDKit Crippen cLogP (Wildman–Crippen atom contributions) for the neutral molecule; measured log P / log D values differ, especially for acids (log D₇.₄ is much lower).
ᵇ Lipinski’s original counts: donors = OH + NH, acceptors = all N + O atoms. MW in g mol⁻¹ (RDKit average mass). Red cells break a rule; two or more violations predict poor oral absorption.
Lipinski (1997): poor absorption or permeation is more likely when a compound has more than 5 H-bond donors, 10 acceptors, MW over 500 or log P over 5: every limit is a multiple of five.
One violation is common in drugs; two or more is the warning. It is a guide for oral drugs made by passive diffusion, not a law.
Substrates of transporters and many natural products (antibiotics, cyclosporine, statins taken up by OATP1B1) are the known exceptions: “beyond rule of five”.
Atorvastatin breaks two rules here yet is an oral drug (14% bioavailable); cyclosporine hides its NH donors in intramolecular H-bonds to cross membranes.
Related filters: Veber (rotatable bonds ≤ 10, polar surface area ≤ 140 Å²) and lead-likeness (MW ≤ 350, log P ≤ 3).
Values computed with RDKit (Crippen cLogP); measured values differ · every part of this sheet is editable

Drawn with 154 atoms, 14 shapes – every one editable in MolDraw.

Sources

Lipinski et al., Adv. Drug Deliv. Rev. 1997, 23, 3 Original paper
Patrick, An Introduction to Medicinal Chemistry, 6th ed., OUP 2017 Textbook

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Frequently asked questions

Is the Lipinski rule of five template free?

Yes. The Lipinski rule of five template is one of the free MolDraw templates: open it in the editor or download it from this page as SVG or PNG and use it in your slides, worksheets and notes.

Can I edit the Lipinski rule of five template?

Yes. It opens as an ordinary MolDraw drawing, so every structure, arrow, label and colour can be changed, and you can add your own content around it.

Is the chemistry checked?

Every structure is checked with RDKit and every curly arrow passes MolDraw’s electron-flow audit. The sources used are listed on this page.

Are the drug structures accurate?

Every structure is checked with RDKit, including its stereocentres, and the sheets follow the medicinal chemistry textbooks listed on each template page.