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. 2020 Feb 26;10:3555. doi: 10.1038/s41598-020-60147-7

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© The Author(s) 2020

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

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Summary of the compounds. ‘K_i (A_2B)’ values are the [³H]-DPCPX binding assay results and ‘cAMP’ values are the adenosine-induced cAMP assay results. Pharmacophore analysis of the compounds was performed. Green, blue, and orange circles represent the hydrogen donor site binding His280^7.43, a hydrogen donor with side-chain binding to Tyr10^1.35, and the common –OCH₃ group close to Ser279^7.42, respectively. Green cross ‘X’ represents the mismatch between the ligand NO₂ group and the pharmacophore. ^#, the values of BAY60-6583 were adopted from van der Hoeven et al.⁴⁴.