RXP470.1   Click here for help

GtoPdb Ligand ID: 7812

PDB Ligand
Compound class: Synthetic organic
Comment: RXP470.1 is a potent and selective MMP-12 inhibitor (Ki 0.24 nM) and 3D structure 4GQL [1]. In 2011 it was reported to reduce atherosclerotic plaque development in apolipoprotein E-knockout mice [2]. A 2014 papert used RXP470.1 to indicate that inhibiting extracellular MMP-12 could be a new avenue for antiviral treatments [3]. There are multiple stereoisomers in PubChem but the structure chosen connects the paper with the PDB structure and the assay data
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 6
Rotatable bonds 20
Topological polar surface area 249.03
Molecular weight 816.1
XLogP 3.98
No. Lipinski's rules broken 3
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Canonical SMILES OC(=O)CCC(C(=O)NC(C(=O)N)CCC(=O)O)NC(=O)C(CP(=O)(c1ccc(cc1)Br)O)Cc1onc(c1)c1ccc(cc1)c1cccc(c1)Cl
Isomeric SMILES OC(=O)CC[C@@H](C(=O)N[C@H](C(=O)N)CCC(=O)O)NC(=O)[C@@H](CP(=O)(c1ccc(cc1)Br)O)Cc1onc(c1)c1ccc(cc1)c1cccc(c1)Cl
InChI InChI=1S/C35H35BrClN4O10P/c36-24-8-10-27(11-9-24)52(49,50)19-23(34(47)40-29(13-15-32(44)45)35(48)39-28(33(38)46)12-14-31(42)43)17-26-18-30(41-51-26)21-6-4-20(5-7-21)22-2-1-3-25(37)16-22/h1-11,16,18,23,28-29H,12-15,17,19H2,(H2,38,46)(H,39,48)(H,40,47)(H,42,43)(H,44,45)(H,49,50)/t23-,28+,29+/m1/s1
1. Czarny B, Stura EA, Devel L, Vera L, Cassar-Lajeunesse E, Beau F, Calderone V, Fragai M, Luchinat C, Dive V. (2013)
Molecular determinants of a selective matrix metalloprotease-12 inhibitor: insights from crystallography and thermodynamic studies.
J Med Chem, 56 (3): 1149-59. [PMID:23343195]
2. Johnson JL, Devel L, Czarny B, George SJ, Jackson CL, Rogakos V, Beau F, Yiotakis A, Newby AC, Dive V. (2011)
A selective matrix metalloproteinase-12 inhibitor retards atherosclerotic plaque development in apolipoprotein E-knockout mice.
Arterioscler Thromb Vasc Biol, 31 (3): 528-35. [PMID:21212406]
3. Marchant DJ, Bellac CL, Moraes TJ, Wadsworth SJ, Dufour A, Butler GS, Bilawchuk LM, Hendry RG, Robertson AG, Cheung CT et al.. (2014)
A new transcriptional role for matrix metalloproteinase-12 in antiviral immunity.
Nat Med, 20 (5): 493-502. [PMID:24784232]