BRD9185   Click here for help

GtoPdb Ligand ID: 11469

Synonyms: compound 27 [PMID: 28435533]
Antimalarial Ligand
Compound class: Synthetic organic
Comment: BRD9185 is the optimized lead from a novel structural class of P. falciparum dihydroorotate dehydrogenase (PfDHODH) inhibitors with potent antimalarial activity [1]. Chemically it is a azetidine-2-carbonitrile compound.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 76.36
Molecular weight 485.15
XLogP 4.51
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCCNC(=O)N1[C@H](CO)[C@H]([C@H]1C#N)c1ccc(cc1)c1ccc(c(c1)C(F)(F)F)C(F)(F)F
Isomeric SMILES CCCNC(=O)N1[C@H](CO)[C@H]([C@H]1C#N)c1ccc(cc1)c1ccc(c(c1)C(F)(F)F)C(F)(F)F
InChI InChI=1S/C23H21F6N3O2/c1-2-9-31-21(34)32-18(11-30)20(19(32)12-33)14-5-3-13(4-6-14)15-7-8-16(22(24,25)26)17(10-15)23(27,28)29/h3-8,10,18-20,33H,2,9,12H2,1H3,(H,31,34)/t18-,19-,20+/m1/s1
InChI Key FYPZBZFXJUJJRA-AQNXPRMDSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
(2S,3S,4S)-3-[4-[3,4-bis(trifluoromethyl)phenyl]phenyl]-2-cyano-4-(hydroxymethyl)-N-propylazetidine-1-carboxamide
Synonyms Click here for help
compound 27 [PMID: 28435533]
Database Links Click here for help
CAS Registry No. 2057420-29-6 (source: Scifinder)
ChEMBL Ligand CHEMBL4064731
GtoPdb PubChem SID 440816837
PubChem CID 121596187
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