Mz438   Click here for help

GtoPdb Ligand ID: 12805

Synonyms: compound 9a [PMID: 37463496] | Mz-438
 Ligand is labelled
Compound class: Synthetic organic
Comment: Mz438 is a fluorescent (TAMRA)-labelled CXCR2 ligand that binds within the receptor's intracellular allosteric binding site [1]. It can be used as a probe in cell-free and cellular assays to investigate CXCR2 pharmacology.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 20
Hydrogen bond donors 5
Rotatable bonds 27
Topological polar surface area 257.12
Molecular weight 1066.17
XLogP 3.63
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES CC1=CC=C([C@@H](C(C)(C)C)NC2=C(C(=O)C2=O)NC3=C(C(=CC=C3)C(=O)NCC4=CN(CCOCCOCCOCCNC(=O)C5=CC(=C(C=C5)C(=O)[O-])C6=C7C=C/C(=[N+](/C)\C)/C=C7OC8=C6C=CC(=C8)N(C)C)N=N4)O)O1
Isomeric SMILES O=C(NCCOCCOCCOCCN1N=NC(CNC(C=2C=CC=C(NC=3C(C(=O)C3N[C@H](C(C)(C)C)C=4OC(=CC4)C)=O)C2O)=O)=C1)C5=CC(C=6C7=C(C=C(N(C)C)C=C7)OC8=C\C(\C=CC68)=[N+](/C)\C)=C(C([O-])=O)C=C5
InChI InChI=1S/C57H63N9O12/c1-33-12-19-44(77-33)53(57(2,3)4)61-49-48(51(68)52(49)69)60-43-11-9-10-41(50(43)67)55(71)59-31-35-32-66(63-62-35)21-23-75-25-27-76-26-24-74-22-20-58-54(70)34-13-16-38(56(72)73)42(28-34)47-39-17-14-36(64(5)6)29-45(39)78-46-30-37(65(7)8)15-18-40(46)47/h9-19,28-30,32,53H,20-27,31H2,1-8H3,(H5-,58,59,60,61,62,63,67,68,69,70,71,72,73)/t53-/m0/s1
InChI Key ULWWLGSAYMCWBM-DTSDQNDWSA-N
References
1. Huber ME, Wurnig S, Toy L, Weiler C, Merten N, Kostenis E, Hansen FK, Schiedel M. (2023)
Fluorescent Ligands Enable Target Engagement Studies for the Intracellular Allosteric Binding Site of the Chemokine Receptor CXCR2.
J Med Chem, 66 (14): 9916-9933. [PMID:37463496]