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XPC-6591   Click here for help

GtoPdb Ligand ID: 13388

Synonyms: XPC6591
Compound class: Synthetic organic
Comment: XPC-6591 is one of a set of brain penetrant voltage-gated sodium channel (NaV) inhibitor compounds that were developed to test the hypothesis that NaV1.6 is the principal determinant of the anti-seizure efficacy of NaV inhibitors [1]. NaV1.6 selectivity reduces side-effects that are caused by less selective inhibitors at additional channel isoforms, namely NaV1.1 (in inhibitory interneurons) and NaV1.5 (in cardiomyocytes).
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 6
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 104.68
Molecular weight 493.59
XLogP 3.19
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 CC1=C(C(=C(C=C1OC2CCN(CC2)[C@H](C)C3=CC=CC=C3)F)S(=O)(=O)NC4=CSC=N4)F
Isomeric SMILES FC1=C(C(=CC(=C1C)OC2CCN(CC2)[C@H](C)C3=CC=CC=C3)F)S(=O)(=O)NC=4N=CSC4
InChI InChI=1S/C23H25F2N3O3S2/c1-15-20(12-19(24)23(22(15)25)33(29,30)27-21-13-32-14-26-21)31-18-8-10-28(11-9-18)16(2)17-6-4-3-5-7-17/h3-7,12-14,16,18,27H,8-11H2,1-2H3/t16-/m1/s1
InChI Key JHYAUINCWJPVDP-MRXNPFEDSA-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/)
References
1. Johnson Jr JP, Focken T, Karimi Tari P, Dube C, Goodchild SJ, Andrez JC, Bankar G, Burford K, Chang E, Chowdhury S et al.. (2024)
The contribution of NaV1.6 to the efficacy of voltage-gated sodium channel inhibitors in wild type and NaV1.6 gain-of-function (GOF) mouse seizure control.
Br J Pharmacol, 181 (20): 3993-4011. [PMID:38922847]