compound 6b [PMID: 22749870]   Click here for help

GtoPdb Ligand ID: 8814

Compound class: Synthetic organic
Comment: Compound 6b was designed to inhibit ferrous ion transport via the divalent metal transporter 1 (DMT1; SLC11A2) [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 4
Rotatable bonds 9
Topological polar surface area 218.78
Molecular weight 425.05
XLogP 3.98
No. Lipinski's rules broken 0
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Canonical SMILES NC(=N)SCc1cc(F)ccc1Sc1ccc(cc1CSC(=N)N)[N+](=O)[O-]
Isomeric SMILES NC(=N)SCc1cc(F)ccc1Sc1ccc(cc1CSC(=N)N)[N+](=O)[O-]
InChI InChI=1S/C16H16FN5O2S3/c17-11-1-3-13(9(5-11)7-25-15(18)19)27-14-4-2-12(22(23)24)6-10(14)8-26-16(20)21/h1-6H,7-8H2,(H3,18,19)(H3,20,21)
Bioactivity Comments
Compound 6b inhibits iron absorption in vivo [1], and represents a chemical scaffold for further optimisation in the search for novel therapeutics for the prevention and treatment of iron overload disorders. Compound 6b does not inhibit the closely related transporter SLC11A1 (NRAMP1).
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
DMT1 Hs Inhibitor Inhibition 7.1 pIC50 - 1
pIC50 7.1 (IC50 8x10-8 M) [1]