(-)-menthol   Click here for help

GtoPdb Ligand ID: 2430

Synonyms: l-menthol | levomenthol
Approved drug
(-)-menthol is an approved drug (FDA (2008), no prior history available)
Comment: Natural menthol principally occurs as the (-)-enantiomer, also known as levomenthol. This (-)-enantiomer is also one of the components of the INN-assigned racementhol.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 20.23
Molecular weight 156.15
XLogP 3.21
No. Lipinski's rules broken 0
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Canonical SMILES CC1CCC(C(C1)O)C(C)C
Isomeric SMILES C[C@@H]1CC[C@H]([C@@H](C1)O)C(C)C
InChI InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
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. Karashima Y, Damann N, Prenen J, Talavera K, Segal A, Voets T, Nilius B. (2007)
Bimodal action of menthol on the transient receptor potential channel TRPA1.
J Neurosci, 27 (37): 9874-84. [PMID:17855602]
4. Macpherson LJ, Hwang SW, Miyamoto T, Dubin AE, Patapoutian A, Story GM. (2006)
More than cool: promiscuous relationships of menthol and other sensory compounds.
Mol Cell Neurosci, 32 (4): 335-43. [PMID:16829128]
5. 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]
6. Voets T, Droogmans G, Wissenbach U, Janssens A, Flockerzi V, Nilius B. (2004)
The principle of temperature-dependent gating in cold- and heat-sensitive TRP channels.
Nature, 430 (7001): 748-54. [PMID:15306801]
7. Xiao B, Dubin AE, Bursulaya B, Viswanath V, Jegla TJ, Patapoutian A. (2008)
Identification of transmembrane domain 5 as a critical molecular determinant of menthol sensitivity in mammalian TRPA1 channels.
J Neurosci, 28 (39): 9640-51. [PMID:18815250]