NPC1161B   Click here for help

GtoPdb Ligand ID: 10393

Synonyms: NPC-1161B
Antimalarial Ligand
Compound class: Synthetic organic
Comment: NPC1161B is a next-generation lead compound for the 8-aminoquinoline class of antimalarial compounds. It is the (-)-enantiomer of NPC1161C [1].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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 3
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 69.4
Molecular weight 433.13
XLogP 4.98
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 NCCCC(Nc1cc(OC)c(c2c1nccc2C)Oc1ccc(c(c1)Cl)Cl)C
Isomeric SMILES NCCC[C@H](Nc1cc(OC)c(c2c1nccc2C)Oc1ccc(c(c1)Cl)Cl)C
InChI InChI=1S/C22H25Cl2N3O2/c1-13-8-10-26-21-18(27-14(2)5-4-9-25)12-19(28-3)22(20(13)21)29-15-6-7-16(23)17(24)11-15/h6-8,10-12,14,27H,4-5,9,25H2,1-3H3/t14-/m1/s1
InChI Key UEFVAUCKVCFRDW-CQSZACIVSA-N
References
1. Nanayakkara NP, Ager Jr AL, Bartlett MS, Yardley V, Croft SL, Khan IA, McChesney JD, Walker LA. (2008)
Antiparasitic activities and toxicities of individual enantiomers of the 8-aminoquinoline 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-4-methyl-5-[3,4-dichlorophenoxy]quinoline succinate.
Antimicrob Agents Chemother, 52 (6): 2130-7. [PMID:18378716]
2. Zeeman AM, van Amsterdam SM, McNamara CW, Voorberg-van der Wel A, Klooster EJ, van den Berg A, Remarque EJ, Plouffe DM, van Gemert GJ, Luty A et al.. (2014)
KAI407, a potent non-8-aminoquinoline compound that kills Plasmodium cynomolgi early dormant liver stage parasites in vitro.
Antimicrob Agents Chemother, 58 (3): 1586-95. [PMID:24366744]