naphthoquine   Click here for help

GtoPdb Ligand ID: 10396

Antimalarial Ligand
Compound class: Synthetic organic
Comment: Naphthoquine is a 4-aminoquinoline antimalarial compound.
The marketed formulations contain naphthoquine phosphate (PubChem CID 9851774).

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 3
Rotatable bonds 5
Topological polar surface area 57.18
Molecular weight 409.19
XLogP 5.83
No. Lipinski's rules broken 1
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 Clc1ccc2c(c1)nccc2Nc1cc(CNC(C)(C)C)c(c2c1CCCC2)O
Isomeric SMILES Clc1ccc2c(c1)nccc2Nc1cc(CNC(C)(C)C)c(c2c1CCCC2)O
InChI InChI=1S/C24H28ClN3O/c1-24(2,3)27-14-15-12-22(17-6-4-5-7-18(17)23(15)29)28-20-10-11-26-21-13-16(25)8-9-19(20)21/h8-13,27,29H,4-7,14H2,1-3H3,(H,26,28)
InChI Key VEVMYTDOWUQLGI-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
2-[(tert-butylamino)methyl]-4-[(7-chloroquinolin-4-yl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol
Database Links Click here for help
CAS Registry No. 173531-57-2 (source: Scifinder)
GtoPdb PubChem SID 384403675
PubChem CID 9851775
Search Google for chemical match using the InChIKey VEVMYTDOWUQLGI-UHFFFAOYSA-N
Search Google for chemicals with the same backbone VEVMYTDOWUQLGI
UniChem Compound Search for chemical match using the InChIKey VEVMYTDOWUQLGI-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey VEVMYTDOWUQLGI-UHFFFAOYSA-N