icosapent   Click here for help

GtoPdb Ligand ID: 7441

Synonyms: AMR-101 | icosapent ethyl | icosapentate | Vascepa® | Vazkepa®
Approved drug
icosapent is an approved drug (FDA (2012), EMA (2021))
Compound class: Synthetic organic
Comment: Icosapent is a synthetic ethyl ester derivative of the omega-3 fatty acid eicosapentaenoic acid (EPA). It is de-esterified during absorption to active EPA that is absorbed in the small intestine.
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 2
Hydrogen bond donors 0
Rotatable bonds 15
Topological polar surface area 26.3
Molecular weight 330.26
XLogP 8.77
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 CCC=CCC=CCC=CCC=CCC=CCCCC(=O)OCC
Isomeric SMILES CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCC
InChI InChI=1S/C22H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24-4-2/h5-6,8-9,11-12,14-15,17-18H,3-4,7,10,13,16,19-21H2,1-2H3/b6-5-,9-8-,12-11-,15-14-,18-17-
InChI Key SSQPWTVBQMWLSZ-AAQCHOMXSA-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2012), EMA (2021))
IUPAC Name Click here for help
ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
International Nonproprietary Names Click here for help
INN number INN
6328 icosapent
Synonyms Click here for help
AMR-101 | icosapent ethyl | icosapentate | Vascepa® | Vazkepa®
Database Links Click here for help
CAS Registry No. 86227-47-6
ChEMBL Ligand CHEMBL2095209
DrugBank Ligand DB08887
DrugCentral Ligand 1413
GtoPdb PubChem SID 178104013
LIPID MAPS LMFA07010877
PubChem CID 9831415
Search Google for chemical match using the InChIKey SSQPWTVBQMWLSZ-AAQCHOMXSA-N
Search Google for chemicals with the same backbone SSQPWTVBQMWLSZ
Search PubMed clinical trials icosapent
Search PubMed titles icosapent
Search PubMed titles/abstracts icosapent
UniChem Compound Search for chemical match using the InChIKey SSQPWTVBQMWLSZ-AAQCHOMXSA-N
UniChem Connectivity Search for chemical match using the InChIKey SSQPWTVBQMWLSZ-AAQCHOMXSA-N
Wikipedia Ethyl eicosapentaenoic acid