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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
4S)-5-amino-4-[[(2S)-2-[[(2S)-2-[[(4-bromophenyl)-hydroxyphosphoryl]methyl]-3-[3-[4-(3-chlorophenyl)phenyl]-1,2-oxazol-5-yl]propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoic acid
Database Links Click here for help
ChEMBL Ligand CHEMBL507420
GtoPdb PubChem SID 223366143
PubChem CID 44580458
RCSB PDB Ligand R47
Search Google for chemical match using the InChIKey PTUCPHGSAFOJAU-MGONOCMRSA-N
Search Google for chemicals with the same backbone PTUCPHGSAFOJAU
SynPHARM 80658 (in complex with MMP12)
UniChem Compound Search for chemical match using the InChIKey PTUCPHGSAFOJAU-MGONOCMRSA-N
UniChem Connectivity Search for chemical match using the InChIKey PTUCPHGSAFOJAU-MGONOCMRSA-N