TIQ-15   Click here for help

GtoPdb Ligand ID: 9882

Compound class: Synthetic organic
Comment: TIQ-15 is a CXCR4 antagonist [1]. It is the parent molecule of the analogue compound 46c [PMID: 29350534]. CXCR4 antagonists are being developed for potential clinical utility as anti-cancer agents. However, TIQ-15 is unsatisfactory as a clinical lead as it suffers from poor oral bioavailability and off-target liabilities (primarily inhibition of the central hepatic drug-metabolising enzyme CYP450 2D6).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 54.18
Molecular weight 364.26
XLogP 2.42
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES NCCCCN(C1CCCc2c1nccc2)CC1NCc2c(C1)cccc2
Isomeric SMILES NCCCCN([C@H]1CCCc2c1nccc2)C[C@@H]1NCc2c(C1)cccc2
InChI InChI=1S/C23H32N4/c24-12-3-4-14-27(22-11-5-9-18-10-6-13-25-23(18)22)17-21-15-19-7-1-2-8-20(19)16-26-21/h1-2,6-8,10,13,21-22,26H,3-5,9,11-12,14-17,24H2/t21-,22+/m1/s1
InChI Key MYCKNKHATQGHEV-YADHBBJMSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N'-[[(3R)-1,2,3,4-tetrahydroisoquinolin-3-yl]methyl]-N'-[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]butane-1,4-diamine
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BindingDB Ligand 50443541
ChEMBL Ligand CHEMBL3091687
GtoPdb PubChem SID 363894176
PubChem CID 57345320
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