(-)-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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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
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRPM8 Mm Activator Partial agonist 4.0 – 5.4 pEC50 - 1-2
⤷ pEC50 4.0 – 5.4 [1-2]
Voltage: Physiological
TRPM8 Primary target of this compound Hs Activator - 4.6 pEC50 - 6
⤷ pEC50 4.6 (EC50 2.51x10-5 M) inhibited by intracellular Ca2+ [6]
Voltage: -120.0 – 160.0 mV
TRPA1 Hs Activator Partial agonist 4.0 – 4.5 pEC50 - 3,7
⤷ pEC50 4.0 – 4.5 (EC50 9.5x10-5 – 2.84x10-5 M) Menthol is also active at the mouse TRPA1, but becomes inhibitory at >100µM [3,7]
Description: Calcium imaging, patch clamp
Conditions: CHO cells expressing human TRPA1
TRPM8 Rn Activator Partial agonist 4.1 – 4.2 pEC50 - 5
⤷ pEC50 4.1 – 4.2 [5]
Voltage: -60.0 mV
TRPV3 Mm Activator Activation 1.7 pEC50 - 4
⤷ pEC50 1.7 (EC50 1.995x10-2 M) [4]
Voltage: -80.0 – 80.0 mV
Description: Patch clamp electrophysiology and calcium imaging
TRPA1 Mm Gating inhibitor Antagonist 4.2 pIC50 - 4
⤷ pIC50 4.2 [4]
Voltage: Physiological
Ligand mentioned in the following text fields
Transient Receptor Potential channels (TRP) comments