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compound 7 [WO2020160054]   Click here for help

GtoPdb Ligand ID: 14506

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: The IUPAC descriptor for this compound was obtained from the FDA's list of Orphan Drug Designations and Approvals [1]. It maps to a chemical structure claimed in patent WO2020160054A1, for activity as a Toll-like receptor 7 (TLR7) and/or TLR8 agonist [2]. We suspect that this is CAN1012 (CanWell Pharma), a selective TLR7 agonist, but the structure of CAN1012 has not been formally disclosed.
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 31
Topological polar surface area 115.86
Molecular weight 746.08
XLogP 11.37
No. Lipinski's rules broken 3

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 CCCCCCCCCCCCCCCCCNC1=C(C(=O)C1=O)N(CCCCON2C(=NC3=C(N)N=C4C=CC=CC4=C32)CCCC)CCCN(C)C
Isomeric SMILES CCCCCCCCCCCCCCCCCNC1=C(C(=O)C1=O)N(CCCCON2C(=NC3=C2C4=CC=CC=C4N=C3N)CCCC)CCCN(C)C
InChI InChI=1S/C44H71N7O3/c1-5-7-9-10-11-12-13-14-15-16-17-18-19-20-23-30-46-38-41(43(53)42(38)52)50(33-26-31-49(3)4)32-24-25-34-54-51-37(29-8-6-2)48-39-40(51)35-27-21-22-28-36(35)47-44(39)45/h21-22,27-28,46H,5-20,23-26,29-34H2,1-4H3,(H2,45,47)
InChI Key QCDHMRIADDJSDR-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/)
Bioactivity Comments
Induces IFNα release from human peripheral blood mononuclear cells (PBMCs) with minimum effective concentration (MEC) of 15 nM [2]. The MEC for TNFα release is >400 nM.