compound 28 [PMID: 31188540]   Click here for help

GtoPdb Ligand ID: 10617

Antimalarial Ligand
Compound class: Synthetic organic
Comment: Compound 28 is the optimized lead from a novel class of antimalarial compounds based on an aminoacetamide scaffold [3].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 96.12
Molecular weight 469.12
XLogP 2.74
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES O=C(C(Nc1ccc(c(c1)S(=O)(=O)N1CCOCC1)C)(C)C)Nc1ccc(c(c1)Cl)F
Isomeric SMILES O=C(C(Nc1ccc(c(c1)S(=O)(=O)N1CCOCC1)C)(C)C)Nc1ccc(c(c1)Cl)F
InChI InChI=1S/C21H25ClFN3O4S/c1-14-4-5-16(13-19(14)31(28,29)26-8-10-30-11-9-26)25-21(2,3)20(27)24-15-6-7-18(23)17(22)12-15/h4-7,12-13,25H,8-11H2,1-3H3,(H,24,27)
InChI Key DUBVSWHYPDKVEA-UHFFFAOYSA-N
Guide to Malaria Pharmacology Comments
Compound selection from GlaxoSmithKline's Tres Cantos antimalarial set (TCAMS) [1-2] was used as the chemical starting point for the identification and optimization of a series of potent P. falciparum inhibitors with an aminoacetamide core. Although this class of compounds is not suitable for progression to pharmacokinetic and efficacy studies, due to metabolic instability and poor aqueous solubility, compound 28 has potential as a lead for further optimization or as a chemical tool for drug target identification [3].

Potential Target/Mechanism Of Action: As the precise mechanism of action of compound 28 is not yet known, we do not have a molecular target for this compound.