orlistat   Click here for help

GtoPdb Ligand ID: 5277

Synonyms: Alli® | tetrahydrolipstatin | THL | Xenical®
Approved drug
orlistat is an approved drug (FDA (1999), EMA (1998))
Compound class: Synthetic organic
Comment: Orlistat is a lipase inhibitor. Lipase enzymes include gastric and pancreatic lipases, diacylglycerol lipase (DAGL) and αβ-hydrolase 12 (ABHD12). It is used as an anti-obesity drug treatment. At least 18 isomeric forms exist in PubChem.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: orlistat

orlistat is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Abramson HN. (2011)
The lipogenesis pathway as a cancer target.
J Med Chem, 54 (16): 5615-38. [PMID:21726077]
2. 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]
3. 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.
4. Chu J, Xing C, Du Y, Duan T, Liu S, Zhang P, Cheng C, Henley J, Liu X, Qian C et al.. (2021)
Pharmacological inhibition of fatty acid synthesis blocks SARS-CoV-2 replication.
Nat Metab, 3 (11): 1466-1475. [PMID:34580494]
5. 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]
6. Richardson RD, Ma G, Oyola Y, Zancanella M, Knowles LM, Cieplak P, Romo D, Smith JW. (2008)
Synthesis of novel beta-lactone inhibitors of fatty acid synthase.
J Med Chem, 51 (17): 5285-96. [PMID:18710210]
7. Williams CG, Jureka AS, Silvas JA, Nicolini AM, Chvatal SA, Carlson-Stevermer J, Oki J, Holden K, Basler CF. (2021)
Inhibitors of VPS34 and fatty-acid metabolism suppress SARS-CoV-2 replication.
Cell Rep, 36 (5): 109479. [PMID:34320401]