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].

omecamtiv mecarbil 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 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

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 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

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
IUPAC Name Click here for help
methyl 4-[[2-fluoro-3-[(6-methylpyridin-3-yl)carbamoylamino]phenyl]methyl]piperazine-1-carboxylate
International Nonproprietary Names Click here for help
INN number INN
9088 omecamtiv mecarbil
Synonyms Click here for help
AMG 423 | AMG-423 | CK-1827452
Database Links Click here for help
CAS Registry No. 873697-71-3 (source: PubChem)
ChEMBL Ligand CHEMBL1800955
GtoPdb PubChem SID 252827398
PubChem CID 11689883
RCSB PDB Ligand 2OW
Search Google for chemical match using the InChIKey RFUBTTPMWSKEIW-UHFFFAOYSA-N
Search Google for chemicals with the same backbone RFUBTTPMWSKEIW
Search PubMed clinical trials omecamtiv mecarbil
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Search PubMed titles/abstracts omecamtiv mecarbil
UniChem Compound Search for chemical match using the InChIKey RFUBTTPMWSKEIW-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey RFUBTTPMWSKEIW-UHFFFAOYSA-N

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MedChemExpress
Omecamtiv mecarbil (links to external site)
Cat. No. HY-14233