ganaplacide   Click here for help

GtoPdb Ligand ID: 9946

Synonyms: GNF156 | KAF156
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Ganaplacide is the optimised lead for the imidazolopiperazines (IZPs), a novel class of compounds identified from a phenotypic screen as having antimalarial activity [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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 5
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 76.18
Molecular weight 411.19
XLogP 4.09
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NCC(=O)N1CCn2c(C1(C)C)nc(c2Nc1ccc(cc1)F)c1ccc(cc1)F
Isomeric SMILES NCC(=O)N1CCn2c(C1(C)C)nc(c2Nc1ccc(cc1)F)c1ccc(cc1)F
InChI InChI=1S/C22H23F2N5O/c1-22(2)21-27-19(14-3-5-15(23)6-4-14)20(26-17-9-7-16(24)8-10-17)28(21)11-12-29(22)18(30)13-25/h3-10,26H,11-13,25H2,1-2H3
InChI Key BUPRVECGWBHCQV-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
2-amino-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone
International Nonproprietary Names Click here for help
INN number INN
10761 ganaplacide
Synonyms Click here for help
GNF156 | KAF156
Database Links Click here for help
CAS Registry No. 1261113-96-5 (source: Scifinder)
ChEMBL Ligand CHEMBL2058833
GtoPdb PubChem SID 374883833
PubChem CID 49856296
Search Google for chemical match using the InChIKey BUPRVECGWBHCQV-UHFFFAOYSA-N
Search Google for chemicals with the same backbone BUPRVECGWBHCQV
Search PubMed clinical trials ganaplacide
Search PubMed titles ganaplacide
Search PubMed titles/abstracts ganaplacide
UniChem Compound Search for chemical match using the InChIKey BUPRVECGWBHCQV-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey BUPRVECGWBHCQV-UHFFFAOYSA-N
Wikipedia KAF156