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
SMILES / InChI / InChIKey
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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
InChI Key PTUCPHGSAFOJAU-MGONOCMRSA-N
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
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SynPHARM 80658 (in complex with MMP12)