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. We have drawn the structure as depicted in Pino et al. (2017) [1], with the indicated stereochemistry (but note that the IUPAC they provide is for the flat structure that is represented by PubChem CID 11619556).
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2D Structure
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Physico-chemical Properties
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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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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
References
1. Pino P, Caldelari R, Mukherjee B, Vahokoski J, Klages N, Maco B, Collins CR, Blackman MJ, Kursula I, Heussler V et al.. (2017)
A multistage antimalarial targets the plasmepsins IX and X essential for invasion and egress.
Science, 358 (6362): 522-528. [PMID:29074775]