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
Bioactivity Comments
Primary target is pancreatic triacylglycerol lipase (P16233) but this compound also inhibits Sn1-specific diacylglycerol lipases α (Q9Y4D2) and β (Q8NCG7).
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
pancreatic lipase Hs Inhibitor Inhibition 8.9 pIC50 - 2
pIC50 8.9 (IC50 1.3x10-9 M) [2]
Diacylglycerol lipase α Hs Inhibitor Inhibition 7.2 pIC50 - 1
pIC50 7.2 (IC50 6x10-8 M) [1]
αβ-Hydrolase 12 Hs Inhibitor Inhibition 7.1 pIC50 - 3
pIC50 7.1 (IC50 8x10-8 M) [3]
Description: Inhibition of recombinant ABHD12 expressed in HEK293T cells, by SDS-PAGE using rhodamine-tagged FP probe.
Diacylglycerol lipase β Hs Inhibitor Inhibition 7.0 pIC50 - 1
pIC50 7.0 (IC50 1x10-7 M) [1]