phenylacetyl-Arg-Val-Arg-4-amidinobenzylamide   Click here for help

GtoPdb Ligand ID: 6564

Synonyms: compound 15 [PMID:20038105] [1]
Compound class: Synthetic organic
Comment: This compound is an inhibitor of furin and furin-like proprotein convertases [1].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 16
Hydrogen bond donors 10
Rotatable bonds 24
Topological polar surface area 295.07
Molecular weight 678.41
XLogP 0.79
No. Lipinski's rules broken 3
Click here for help
Canonical SMILES NC(=NCCCC(C(=O)NCc1ccc(cc1)C(=N)N)NC(=O)C(C(C)C)NC(=O)C(NC(=O)Cc1ccccc1)CCCN=C(N)N)N
Isomeric SMILES NC(=NCCC[C@@H](C(=O)NCc1ccc(cc1)C(=N)N)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)Cc1ccccc1)CCCN=C(N)N)N
InChI InChI=1S/C33H50N12O4/c1-20(2)27(45-30(48)25(11-7-17-41-33(38)39)43-26(46)18-21-8-4-3-5-9-21)31(49)44-24(10-6-16-40-32(36)37)29(47)42-19-22-12-14-23(15-13-22)28(34)35/h3-5,8-9,12-15,20,24-25,27H,6-7,10-11,16-19H2,1-2H3,(H3,34,35)(H,42,47)(H,43,46)(H,44,49)(H,45,48)(H4,36,37,40)(H4,38,39,41)/t24-,25-,27-/m0/s1
Bioactivity Comments
This compound has comparable affinity for other proprotein convertases such as PCSK1, PACE4 (PCSK6), and PCSK5. This is in contrast to PCSK2, PCSK7 and trypsin-like serine proteases which are poorly inhibited by this compound.
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
proprotein convertase subtilisin/kexin type 6 Hs Inhibitor Inhibition 9.2 pKi - 1
pKi 9.2 (Ki 6x10-10 M) [1]
proprotein convertase subtilisin/kexin type 1 Hs Inhibitor Inhibition 9.1 pKi - 1
pKi 9.1 (Ki 7.5x10-10 M) [1]
furin, paired basic amino acid cleaving enzyme Hs Inhibitor Inhibition 9.1 pKi - 1
pKi 9.1 (Ki 8.1x10-10 M) [1]
proprotein convertase subtilisin/kexin type 5 Hs Inhibitor Inhibition 8.8 pKi - 1
pKi 8.8 (Ki 1.6x10-9 M) [1]