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pentafluoro-trityl clotrimazole analogue 29a   Click here for help

GtoPdb Ligand ID: 12535

Compound class: Synthetic organic
Comment: This clotrimazole-based compound is a modulator (agonist) of the TRPM3 ion channel [1].
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 2
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 15.6
Molecular weight 400.34
XLogP 3.61
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 C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=C(C(=C(C(=C3F)F)F)F)F)N4C=CN=C4
Isomeric SMILES FC1=C(F)C(F)=C(C(F)=C1F)C(C2=CC=CC=C2)(C3=CC=CC=C3)N4C=CN=C4
InChI InChI=1S/C22H13F5N2/c23-17-16(18(24)20(26)21(27)19(17)25)22(29-12-11-28-13-29,14-7-3-1-4-8-14)15-9-5-2-6-10-15/h1-13H
InChI Key IXZCSHNAKAZHCC-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/)
References
1. Kahler JP, Aloi VD, Miedes Aliaga J, Kerselaers S, Voets T, Vriens J, Verhelst SHL, Barniol-Xicota M. (2023)
Clotrimazole-Based Modulators of the TRPM3 Ion Channel Reveal Narrow Structure-Activity Relationship.
ACS Chem Biol, 18 (3): 456-464. [PMID:36762958]