WLL-vs   Click here for help

GtoPdb Ligand ID: 11321

Antimalarial Ligand
Compound class: Synthetic organic
Comment: The peptide vinyl sulfone, WLL-vs, is a highly selective covalent inhibitor of the P. falciparum proteasome [1].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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 10
Hydrogen bond donors 4
Rotatable bonds 18
Topological polar surface area 158.08
Molecular weight 617.32
XLogP 3.4
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CC(C[C@@H](C(=O)N[C@@H](CC(C)C)/C=C/S(=O)(=O)C)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)CN1CCOCC1)C
Isomeric SMILES CC(C[C@@H](C(=O)N[C@@H](CC(C)C)/C=C/S(=O)(=O)C)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)CN1CCOCC1)C
InChI InChI=1S/C31H47N5O6S/c1-21(2)16-24(10-15-43(5,40)41)33-30(38)27(17-22(3)4)35-31(39)28(34-29(37)20-36-11-13-42-14-12-36)18-23-19-32-26-9-7-6-8-25(23)26/h6-10,15,19,21-22,24,27-28,32H,11-14,16-18,20H2,1-5H3,(H,33,38)(H,34,37)(H,35,39)/b15-10+/t24-,27+,28+/m1/s1
InChI Key DKBAFRHAWTVKAD-ODGLJRBPSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
(2S)-2-[[(2S)-3-(1H-indol-3-yl)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]-4-methyl-N-[(E,3S)-5-methyl-1-methylsulfonylhex-1-en-3-yl]pentanamide
Database Links Click here for help
ChEBI CHEBI:91210
ChEMBL Ligand CHEMBL4456306
GtoPdb PubChem SID 434321756
PubChem CID 118796903
Search Google for chemical match using the InChIKey DKBAFRHAWTVKAD-ODGLJRBPSA-N
Search Google for chemicals with the same backbone DKBAFRHAWTVKAD
Search UniChem for chemical match using the InChIKey DKBAFRHAWTVKAD-ODGLJRBPSA-N
Search UniChem for chemicals with the same backbone DKBAFRHAWTVKAD