LUF7602   

GtoPdb Ligand ID: 10351

Synonyms: compound 17b [PMID: 30869893] | LUF-7602
Compound class: Synthetic organic
Comment: LUF7602 is a covalent (i.e. irreversible) antagonist of the adenosine A3 receptor [1]. The fluorosulfonyl warhead binds to amino acid residue Y265 of the receptor. LUF7602 does not bind to a mutant human A3R in which the tyrosine 265 residue is replaced by phenylalanine (Y265F), confirming this residue as the anchor site for the covalent interaction.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 142.15
Molecular weight 531.16
XLogP 5.09
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCCn1c(=O)c2n3ccc(cc3nc2n(c1=O)CCCCNC(=O)c1ccc(cc1)S(=O)(=O)F)OC
Isomeric SMILES CCCn1c(=O)c2n3ccc(cc3nc2n(c1=O)CCCCNC(=O)c1ccc(cc1)S(=O)(=O)F)OC
InChI InChI=1S/C24H26FN5O6S/c1-3-12-30-23(32)20-21(27-19-15-17(36-2)10-14-28(19)20)29(24(30)33)13-5-4-11-26-22(31)16-6-8-18(9-7-16)37(25,34)35/h6-10,14-15H,3-5,11-13H2,1-2H3,(H,26,31)
InChI Key WUZBOJXXYMKMMF-UHFFFAOYSA-N
References
1. Yang X, van Veldhoven JPD, Offringa J, Kuiper BJ, Lenselink EB, Heitman LH, van der Es D, IJzerman AP. (2019)
Development of Covalent Ligands for G Protein-Coupled Receptors: A Case for the Human Adenosine A3 Receptor.
J. Med. Chem., 62 (7): 3539-3552. DOI: 10.1021/acs.jmedchem.8b02026 [PMID:30869893]