omecamtiv mecarbil   Click here for help

GtoPdb Ligand ID: 8740

Synonyms: AMG 423 | AMG-423 | CK-1827452
PDB Ligand
Compound class: Synthetic organic
Comment: Omecamtiv mecarbil is an investigational small molecule which is a direct activator of cardiac myosin [3]. This compound is being investigated as a novel therapy for patients with chronic heart failure due to systolic dysfunction. Results from the first-in-man study are reported by Teerlink et al. (2011) [4].
Omecamtiv mecarbil is claimed in patent US7507735 B2 [2].
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 8
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 86.8
Molecular weight 401.19
XLogP 1.06
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 COC(=O)N1CCN(CC1)Cc1cccc(c1F)NC(=O)Nc1ccc(nc1)C
Isomeric SMILES COC(=O)N1CCN(CC1)Cc1cccc(c1F)NC(=O)Nc1ccc(nc1)C
InChI InChI=1S/C20H24FN5O3/c1-14-6-7-16(12-22-14)23-19(27)24-17-5-3-4-15(18(17)21)13-25-8-10-26(11-9-25)20(28)29-2/h3-7,12H,8-11,13H2,1-2H3,(H2,23,24,27)
InChI Key RFUBTTPMWSKEIW-UHFFFAOYSA-N
Bioactivity Comments
In vitro, active compounds from patent US7507735 B2 (such as omecamtiv mecarbil) increase rat cardiac myocyte contractility with an IC20 of approximately 200nM [2]. This action does not increase the magnitude or change the kinetics of the calcium transient at concentrations up to 10 µM, and the compounds don't inhibit phosphodiesterase type 3. Despite in vitro and in vivo experiments which verify the effects of omecamtiv mecarbil on cardiac mysosin activity, no affinity data is available to corroborate the interaction of the compound with a specified human protein target.