JPC-3210   Click here for help

GtoPdb Ligand ID: 10395

Synonyms: MMV646 | MMV892646
Antimalarial Ligand
Compound class: Synthetic organic
Comment: JPC-3210 has been identified as the lead for the 2-aminomethylphenol class of compounds and demonstrates promising antimalarial activity [3].

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 2
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 45.15
Molecular weight 398.2
XLogP 6.54
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 Oc1c(CNC(C)(C)C)cc(cc1c1cnc(c(c1)F)C(F)(F)F)C(C)(C)C
Isomeric SMILES Oc1c(CNC(C)(C)C)cc(cc1c1cnc(c(c1)F)C(F)(F)F)C(C)(C)C
InChI InChI=1S/C21H26F4N2O/c1-19(2,3)14-7-13(11-27-20(4,5)6)17(28)15(9-14)12-8-16(22)18(26-10-12)21(23,24)25/h7-10,27-28H,11H2,1-6H3
InChI Key DYULPLHABFGTOQ-UHFFFAOYSA-N
References
1. Birrell GW, Challis MP, De Paoli A, Anderson D, Devine SM, Heffernan GD, Jacobus DP, Edstein MD, Siddiqui G, Creek DJ. (2020)
Multi-omic Characterization of the Mode of Action of a Potent New Antimalarial Compound, JPC-3210, Against Plasmodium falciparum.
Mol Cell Proteomics, 19 (2): 308-325. [PMID:31836637]
2. Birrell GW, Heffernan GD, Schiehser GA, Anderson J, Ager AL, Morales P, MacKenzie D, van Breda K, Chavchich M, Jacobus LR et al.. (2018)
Characterization of the Preclinical Pharmacology of the New 2-Aminomethylphenol, JPC-3210, for Malaria Treatment and Prevention.
Antimicrob Agents Chemother, 62 (4). [PMID:29311093]
3. Chavchich M, Birrell GW, Ager AL, MacKenzie DO, Heffernan GD, Schiehser GA, Jacobus LR, Shanks GD, Jacobus DP, Edstein MD. (2016)
Lead Selection of a New Aminomethylphenol, JPC-3210, for Malaria Treatment and Prevention.
Antimicrob Agents Chemother, 60 (5): 3115-8. [PMID:26856849]