ezetimibe   Click here for help

GtoPdb Ligand ID: 6816

Synonyms: SCH 58235 | SCH-58235 | Zetia®
Approved drug PDB Ligand
ezetimibe is an approved drug (FDA (2002))
Compound class: Synthetic organic
Comment: Inhibits the intestinal cholesterol uptake protein Niemann-Pick C1-like protein 1 (NPC1L1). Analysis of cryo-EM structures reveals how NPC1L1 transports cholesterol and the mechanism of ezetimibe inhibition [2].
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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

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View more information in the IUPHAR Pharmacology Education Project: ezetimibe

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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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 CDK toolkit. 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 3
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 60.77
Molecular weight 409.15
XLogP 4.46
No. Lipinski's rules broken 0
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.

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Canonical SMILES Oc1ccc(cc1)C1C(CCC(c2ccc(cc2)F)O)C(=O)N1c1ccc(cc1)F
Isomeric SMILES Oc1ccc(cc1)[C@@H]1[C@@H](CC[C@@H](c2ccc(cc2)F)O)C(=O)N1c1ccc(cc1)F
InChI InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m1/s1
InChI Key OLNTVTPDXPETLC-XPWALMASSA-N
References
1. Garcia-Calvo M, Lisnock J, Bull HG, Hawes BE, Burnett DA, Braun MP, Crona JH, Davis Jr HR, Dean DC, Detmers PA et al.. (2005)
The target of ezetimibe is Niemann-Pick C1-Like 1 (NPC1L1).
Proc Natl Acad Sci USA, 102 (23): 8132-7. [PMID:15928087]
2. Huang CS, Yu X, Fordstrom P, Choi K, Chung BC, Roh SH, Chiu W, Zhou M, Min X, Wang Z. (2020)
Cryo-EM structures of NPC1L1 reveal mechanisms of cholesterol transport and ezetimibe inhibition.
Sci Adv, 6 (25): eabb1989. DOI: 10.1126/sciadv.abb1989 [PMID:32596471]
3. Oswald S, König J, Lütjohann D, Giessmann T, Kroemer HK, Rimmbach C, Rosskopf D, Fromm MF, Siegmund W. (2008)
Disposition of ezetimibe is influenced by polymorphisms of the hepatic uptake carrier OATP1B1.
Pharmacogenet Genomics, 18 (7): 559-68. [PMID:18551036]