(-)-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)
Compound class: Natural product or derivative
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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key NOOLISFMXDJSKH-KXUCPTDWSA-N
References
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]