SQ-109   Click here for help

GtoPdb Ligand ID: 7997

Synonyms: MMV687273 | SQ 109 | SQ109
Antimalarial Ligand
Compound class: Synthetic organic
Comment: SQ-109 is a [1,2]-diamine-based ethambutol analogue included in the Medicines for Malaria Pandemic Response Box (MMV PRB). Functionally, it inhibits Mycobacterial membrane protein large 3 (MmpL3) and has advanced to clinical evaluation for the treatment of tuberculosis [5].

The compound also has antimalarial activity. 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 2
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 24.06
Molecular weight 330.3
XLogP 5.22
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CC(=CCNCCNC1C2CC3CC1CC(C2)C3)CCC=C(C)C
Isomeric SMILES C/C(=C\CNCCNC1C2CC3CC1CC(C2)C3)/CCC=C(C)C
InChI InChI=1S/C22H38N2/c1-16(2)5-4-6-17(3)7-8-23-9-10-24-22-20-12-18-11-19(14-20)15-21(22)13-18/h5,7,18-24H,4,6,8-15H2,1-3H3/b17-7+
InChI Key JFIBVDBTCDTBRH-REZTVBANSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
N'-(2-adamantyl)-N-[(2E)-3,7-dimethylocta-2,6-dienyl]ethane-1,2-diamine
Synonyms Click here for help
MMV687273 | SQ 109 | SQ109
Database Links Click here for help
CAS Registry No. 502487-67-4 (source: Scifinder)
ChEMBL Ligand CHEMBL561057
GtoPdb PubChem SID 249565677
PubChem CID 5274428
Search Google for chemical match using the InChIKey JFIBVDBTCDTBRH-REZTVBANSA-N
Search Google for chemicals with the same backbone JFIBVDBTCDTBRH
Search UniChem for chemical match using the InChIKey JFIBVDBTCDTBRH-REZTVBANSA-N
Search UniChem for chemicals with the same backbone JFIBVDBTCDTBRH
Wikipedia SQ109