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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2D Structure
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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2002))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
8010 ezetimibe
Synonyms Click here for help
SCH 58235 | SCH-58235 | Zetia®
Database Links Click here for help
CAS Registry No. 163222-33-1
ChEMBL Ligand CHEMBL1138
DrugBank Ligand DB00973
DrugCentral Ligand 1125
GtoPdb PubChem SID 178103422
PubChem CID 150311
RCSB PDB Ligand H56
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Search Google for chemicals with the same backbone OLNTVTPDXPETLC
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UniChem Compound Search for chemical match using the InChIKey OLNTVTPDXPETLC-XPWALMASSA-N
UniChem Connectivity Search for chemical match using the InChIKey OLNTVTPDXPETLC-XPWALMASSA-N
Wikipedia Ezetimibe