(-)-menthol   Click here for help

GtoPdb Ligand ID: 2430

Synonyms: l-menthol | levomenthol
Approved drug PDB Ligand
(-)-menthol is an approved drug (FDA (2008), no prior history available)
Compound class: Natural product
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

(-)-menthol is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
Approved drug? Yes. FDA (2008)
IUPAC Name Click here for help
(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol
International Nonproprietary Names Click here for help
INN number INN
6725 levomenthol
6724 racementhol
Synonyms Click here for help
l-menthol | levomenthol
Database Links Click here for help
BindingDB Ligand 50318482
CAS Registry No. 89-78-1 (source: Scifinder)
ChEBI CHEBI:15409
ChEMBL Ligand CHEMBL470670
DrugBank Ligand DB00825
DrugCentral Ligand 934
GtoPdb PubChem SID 135651519
LIPID MAPS LMPR0102090001
PubChem CID 16666
RCSB PDB Ligand XUQ
Search Google for chemical match using the InChIKey NOOLISFMXDJSKH-KXUCPTDWSA-N
Search Google for chemicals with the same backbone NOOLISFMXDJSKH
Search PubMed clinical trials racementhol
Search PubMed titles racementhol
Search PubMed titles/abstracts racementhol
UniChem Compound Search for chemical match using the InChIKey NOOLISFMXDJSKH-KXUCPTDWSA-N
UniChem Connectivity Search for chemical match using the InChIKey NOOLISFMXDJSKH-KXUCPTDWSA-N
Wikipedia Menthol

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MedChemExpress
(-)-Menthol (links to external site)
Cat. No. HY-75161
(Same InChi Key)
DL-Menthol (links to external site)
Cat. No. HY-Y1683