icilin   Click here for help

GtoPdb Ligand ID: 2429

PDB Ligand
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 95.71
Molecular weight 311.09
XLogP 2.73
No. Lipinski's rules broken 0
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Canonical SMILES O=C1NC(=CCN1c1ccccc1O)c1cccc(c1)[N+](=O)[O-]
Isomeric SMILES O=C1NC(=CCN1c1ccccc1O)c1cccc(c1)[N+](=O)[O-]
InChI InChI=1S/C16H13N3O4/c20-15-7-2-1-6-14(15)18-9-8-13(17-16(18)21)11-4-3-5-12(10-11)19(22)23/h1-8,10,20H,9H2,(H,17,21)
1. Andersson DA, Chase HW, Bevan S. (2004)
TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH.
J Neurosci, 24 (23): 5364-9. [PMID:15190109]
2. Behrendt HJ, Germann T, Gillen C, Hatt H, Jostock R. (2004)
Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay.
Br J Pharmacol, 141 (4): 737-45. [PMID:14757700]
3. McKemy DD, Neuhausser WM, Julius D. (2002)
Identification of a cold receptor reveals a general role for TRP channels in thermosensation.
Nature, 416 (6876): 52-8. [PMID:11882888]
4. Myers BR, Sigal YM, Julius D. (2009)
Evolution of thermal response properties in a cold-activated TRP channel.
PLoS ONE, 4 (5): e5741. [PMID:19492038]
5. Peier AM, Moqrich A, Hergarden AC, Reeve AJ, Andersson DA, Story GM, Earley TJ, Dragoni I, McIntyre P, Bevan S et al.. (2002)
A TRP channel that senses cold stimuli and menthol.
Cell, 108 (5): 705-15. [PMID:11893340]
6. Story GM, Peier AM, Reeve AJ, Eid SR, Mosbacher J, Hricik TR, Earley TJ, Hergarden AC, Andersson DA, Hwang SW et al.. (2003)
ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures.
Cell, 112 (6): 819-29. [PMID:12654248]