compound 49c [PMID: 29074775]   Click here for help

GtoPdb Ligand ID: 10418

Antimalarial Ligand
Compound class: Synthetic organic
Comment: Compound 49c is a hydroxyl-ethyl-amine-based scaffold compound with antimalarial activity [1]. We have drawn the structure as depicted in Pino et al. (2017) [2], with the indicated stereochemistry (but note that the IUPAC they provide is for the flat structure that is represented by PubChem CID 11619556).

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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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.

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Physico-chemical Properties
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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.

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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 84.91
Molecular weight 514.29
XLogP 3.7
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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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.

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Canonical SMILES CN1CCN(CC1)C(=O)c1ccc(cc1)C(=O)NC(C(CNC(c1ccccc1)C)O)Cc1ccccc1
Isomeric SMILES CN1CCN(CC1)C(=O)c1ccc(cc1)C(=O)N[C@H]([C@@H](CN[C@@H](c1ccccc1)C)O)Cc1ccccc1
InChI InChI=1S/C31H38N4O3/c1-23(25-11-7-4-8-12-25)32-22-29(36)28(21-24-9-5-3-6-10-24)33-30(37)26-13-15-27(16-14-26)31(38)35-19-17-34(2)18-20-35/h3-16,23,28-29,32,36H,17-22H2,1-2H3,(H,33,37)/t23-,28+,29-/m1/s1
InChI Key NCNJHAHPOUUEQX-LDVROUIZSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
N-[(2S,3R)-3-Hydroxy-1-phenyl-4-[[(1R)-1-phenylethyl]amino]butan-2-yl]-4-(4-methylpiperazine-1-carbonyl)benzamide
Database Links Click here for help
ChEMBL Ligand CHEMBL2334045
GtoPdb PubChem SID 385612178
PubChem CID 71521073
Search Google for chemical match using the InChIKey NCNJHAHPOUUEQX-LDVROUIZSA-N
Search Google for chemicals with the same backbone NCNJHAHPOUUEQX
UniChem Compound Search for chemical match using the InChIKey NCNJHAHPOUUEQX-LDVROUIZSA-N
UniChem Connectivity Search for chemical match using the InChIKey NCNJHAHPOUUEQX-LDVROUIZSA-N