eleclazine   Click here for help

GtoPdb Ligand ID: 8413

Synonyms: GS-6615 | GS6615
Compound class: Synthetic organic
Comment: Eleclazine is a sodium channel inhibitor, modulating cardiac late Na+ currents via the Nav1.5 (gene symbol SCN5A) channel. The compound is a dihydrobenzodiazepine type structure. Dihydrobenzodiazepine scaffolds are being developed as α-helix mimetics, with the potential to inhibit protein-protein interactions [1,3-5]. This chemical structure and its use is covered by patent US20150038489 [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 4
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 64.55
Molecular weight 415.11
XLogP 3.89
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 O=C1N(CCOc2c1cc(cc2)c1ccc(cc1)OC(F)(F)F)Cc1ncccn1
Isomeric SMILES O=C1N(CCOc2c1cc(cc2)c1ccc(cc1)OC(F)(F)F)Cc1ncccn1
InChI InChI=1S/C21H16F3N3O3/c22-21(23,24)30-16-5-2-14(3-6-16)15-4-7-18-17(12-15)20(28)27(10-11-29-18)13-19-25-8-1-9-26-19/h1-9,12H,10-11,13H2
InChI Key YNUAEEJQYHYLMS-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
4-(pyrimidin-2-ylmethyl)-7-[4-(trifluoromethoxy)phenyl]-2,3-dihydro-1,4-benzoxazepin-5-one
International Nonproprietary Names Click here for help
INN number INN
9978 eleclazine
Synonyms Click here for help
GS-6615 | GS6615
Database Links Click here for help
CAS Registry No. 1443211-72-0
GtoPdb PubChem SID 252166623
PubChem CID 71183216
Search Google for chemical match using the InChIKey YNUAEEJQYHYLMS-UHFFFAOYSA-N
Search Google for chemicals with the same backbone YNUAEEJQYHYLMS
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UniChem Compound Search for chemical match using the InChIKey YNUAEEJQYHYLMS-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey YNUAEEJQYHYLMS-UHFFFAOYSA-N