capsaicin   Click here for help

GtoPdb Ligand ID: 2486

Synonyms: Qutenza®
Approved drug PDB Ligand
capsaicin is an approved drug (EMA & FDA (2009))
Compound class: Natural product or derivative
Comment: Although capsaicin was approved by the US FDA in 2009, this compound was previously marketed so was not subject to a New Drug Application.
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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

capsaicin 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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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 2
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 58.56
Molecular weight 305.2
XLogP 4.32
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 COc1cc(CNC(=O)CCCCC=CC(C)C)ccc1O
Isomeric SMILES COc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O
InChI InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+
InChI Key YKPUWZUDDOIDPM-SOFGYWHQSA-N
References
1. Caterina MJ, Schumacher MA, Tominaga M, Rosen TA, Levine JD, Julius D. (1997)
The capsaicin receptor: a heat-activated ion channel in the pain pathway.
Nature, 389 (6653): 816-24. [PMID:9349813]
2. Correll CC, Phelps PT, Anthes JC, Umland S, Greenfeder S. (2004)
Cloning and pharmacological characterization of mouse TRPV1.
Neurosci Lett, 370 (1): 55-60. [PMID:15489017]
3. Grissmer S, Nguyen AN, Aiyar J, Hanson DC, Mather RJ, Gutman GA, Karmilowicz MJ, Auperin DD, Chandy KG. (1994)
Pharmacological characterization of five cloned voltage-gated K+ channels, types Kv1.1, 1.2, 1.3, 1.5, and 3.1, stably expressed in mammalian cell lines.
Mol Pharmacol, 45 (6): 1227-34. [PMID:7517498]
4. Kalman K, Nguyen A, Tseng-Crank J, Dukes ID, Chandy G, Hustad CM, Copeland NG, Jenkins NA, Mohrenweiser H, Brandriff B et al.. (1998)
Genomic organization, chromosomal localization, tissue distribution, and biophysical characterization of a novel mammalian Shaker-related voltage-gated potassium channel, Kv1.7.
J Biol Chem, 273 (10): 5851-7. [PMID:9488722]
5. 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]