orlistat   

GtoPdb Ligand ID: 5277

Synonyms: Alli® | tetrahydrolipstatin | THL | Xenical®
orlistat is an approved drug (FDA (1999), EMA (1998))
Compound class: Synthetic organic
Comment: Orlistat is a lipase inhibitor. Lipase targets include gastric and pancreatic lipases, diacylglycerol lipase (DAGL) and αβ-hydrolase 12 (ABHD12) inhibitor. It is used as an anti-obesity drug treatment. At least 18 isomeric forms exist in PubChem.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 24
Topological polar surface area 81.7
Molecular weight 495.39
XLogP 10.26
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES CCCCCCCCCCCC(CC1OC(=O)C1CCCCCC)OC(=O)C(CC(C)C)NC=O
Isomeric SMILES CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
InChI InChI=1S/C29H53NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h22-27H,5-21H2,1-4H3,(H,30,31)/t24-,25-,26-,27-/m0/s1
InChI Key AHLBNYSZXLDEJQ-FWEHEUNISA-N
References
1. Bisogno T, Howell F, Williams G, Minassi A, Cascio MG, Ligresti A, Matias I, Schiano-Moriello A, Paul P, Williams EJ et al.. (2003)
Cloning of the first sn1-DAG lipases points to the spatial and temporal regulation of endocannabinoid signaling in the brain.
J. Cell Biol., 163 (3): 463-8. [PMID:14610053]
2. Bustanji Y, Issa A, Mohammed M, Hudaib M, Tawah, K, Alkhatib H, Almarsi I, Al-Khalidi B. (2010)
Inhibition of hormone sensitive lipase and pancreatic lipase by Rosmarinus officinalis extract and selected phenolic constituents.
Journal of Medicinal Plants Research, 4 (21): 2235-2242.
3. Hoover HS, Blankman JL, Niessen S, Cravatt BF. (2008)
Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling.
Bioorg. Med. Chem. Lett., 18 (22): 5838-41. [PMID:18657971]