EC18   Click here for help

GtoPdb Ligand ID: 6262

Compound class: Synthetic organic
Comment: EC18 selectively blocks HCN4 channel currents. Its power to discriminate between HCN channel isoforms makes it an ideal chemical probe to stiudy the physiological and pathological roles of HCN4 channel currents in cells and tissues [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
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 0
Rotatable bonds 9
Topological polar surface area 60.47
Molecular weight 496.29
XLogP 3.64
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 COc1ccc(cc1OC)CCN(C1CCCC(C1)N1CCc2c(CC1=O)cc(c(c2)OC)OC)C
Isomeric SMILES COc1ccc(cc1OC)CCN(C1CCCC(C1)N1CCc2c(CC1=O)cc(c(c2)OC)OC)C
InChI InChI=1S/C29H40N2O5/c1-30(13-11-20-9-10-25(33-2)26(15-20)34-3)23-7-6-8-24(19-23)31-14-12-21-16-27(35-4)28(36-5)17-22(21)18-29(31)32/h9-10,15-17,23-24H,6-8,11-14,18-19H2,1-5H3
InChI Key IUAVZEYOWYFRAS-UHFFFAOYSA-N
References
1. Del Lungo M, Melchiorre M, Guandalini L, Sartiani L, Mugelli A, Koncz I, Szel T, Varro A, Romanelli MN, Cerbai E. (2012)
Novel blockers of hyperpolarization-activated current with isoform selectivity in recombinant cells and native tissue.
Br J Pharmacol, 166 (2): 602-16. [PMID:22091830]
2. Romanelli MN, Del Lungo M, Guandalini L, Zobeiri M, Gyökeres A, Árpádffy-Lovas T, Koncz I, Sartiani L, Bartolucci G, Dei S et al.. (2019)
EC18 as a Tool To Understand the Role of HCN4 Channels in Mediating Hyperpolarization-Activated Current in Tissues.
ACS Med Chem Lett, 10 (4): 584-589. DOI: 10.1021/acsmedchemlett.8b00587 [PMID:30996800]