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bempedoic acid   Click here for help

GtoPdb Ligand ID: 8321

Synonyms: ESP-55016 | ETC-1002 | Nexletol® | Nilemdo®
Approved drug PDB Ligand
bempedoic acid is an approved drug (EMA & FDA (2020))
Compound class: Synthetic organic
Comment: Bempedoic acid (ETC-1002) is an orally delivered non-statin drug for treating dyslipidemia and related cardiovascular disease, which offers an additional pharmaceutical strategy for statin-refractory or statin-intolerant patients [1,4,6]. Its novel mechanism of action makes it the first-in-class ATP citrate lyase (ACLY; P53396) inhibitor to reach the clinic [8]. Bempedoic acid is in fact a prodrug, as it must be converted to its active metabolite bempedoic acid-CoA by endogenous liver acyl-CoA synthetase. Bempedoic acid-CoA is the bona fide ACLY inhibitor. ACLY is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA, which in turn is required for de novo lipogenesis and cholesterogenesis, and its inhibition directly reduces cholesterol synthesis in the liver [3].
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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

bempedoic acid 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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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 5
Hydrogen bond donors 3
Rotatable bonds 14
Topological polar surface area 94.83
Molecular weight 344.26
XLogP 4.03
No. Lipinski's rules broken 1

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 OC(CCCCCC(C(=O)O)(C)C)CCCCCC(C(=O)O)(C)C
Isomeric SMILES OC(CCCCCC(C(=O)O)(C)C)CCCCCC(C(=O)O)(C)C
InChI InChI=1S/C19H36O5/c1-18(2,16(21)22)13-9-5-7-11-15(20)12-8-6-10-14-19(3,4)17(23)24/h15,20H,5-14H2,1-4H3,(H,21,22)(H,23,24)
InChI Key HYHMLYSLQUKXKP-UHFFFAOYSA-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. EU EMA (2020)  |  US FDA (2020)
IUPAC Name Click here for help
8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid
International Nonproprietary Names Click here for help
INN number INN
9891 bempedoic acid
Synonyms Click here for help
ESP-55016 | ETC-1002 | Nexletol® | Nilemdo®
Database Links Click here for help
CAS Registry No. 738606-46-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL3545313
DrugCentral Ligand 5382
GtoPdb PubChem SID 252166533
PubChem CID 10472693
RCSB PDB Ligand A1JTY
Search Google for chemical match using the InChIKey HYHMLYSLQUKXKP-UHFFFAOYSA-N
Search Google for chemicals with the same backbone HYHMLYSLQUKXKP
Search PubMed clinical trials bempedoic acid
Search PubMed titles bempedoic acid
Search PubMed titles/abstracts bempedoic acid
UniChem Compound Search for chemical match using the InChIKey HYHMLYSLQUKXKP-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey HYHMLYSLQUKXKP-UHFFFAOYSA-N

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MedChemExpress
Bempedoic acid (links to external site)
Cat. No. HY-12357