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psilocybin   Click here for help

GtoPdb Ligand ID: 14389

Synonyms: Psilocibin
PDB Ligand
Compound class: Natural product
Comment: Psilocybin is a tryptamine alkaloid that is recognised as the major hallucinogenic component in Psilocybe mushrooms. It is metabolized to psilocin. Serotonergic agonist activity likely underlies bioactivity, with reported agonism at serotonin 5-HT2 receptors [4].
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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 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 6
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 91.84
Molecular weight 284.25
XLogP -0.43
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 CN(C)CCC1=CNC2=CC=CC(=C12)OP(=O)(O)O
Isomeric SMILES CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O
InChI InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)
InChI Key QVDSEJDULKLHCG-UHFFFAOYSA-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/)
References
1. Erritzoe D, Barba T, Greenway KT, Murphy R, Martell J, Giribaldi B, Timmermann C, Murphy-Beiner A, Jones MB, Nutt D et al.. (2024)
Effect of psilocybin versus escitalopram on depression symptom severity in patients with moderate-to-severe major depressive disorder: observational 6-month follow-up of a phase 2, double-blind, randomised, controlled trial.
EClinicalMedicine, 76: 102799. [PMID:39764567]
2. Kirlić N, Lennard-Jones M, Atli M, Malievskaia E, Modlin NL, Peck SK, Gaillard A, Goodwin GM, Koelpin D. (2025)
Compass Psychological Support Model for COMP360 Psilocybin Treatment of Serious Mental Health Conditions.
Am J Psychiatry, 182 (1): 126-132. [PMID:39741434]
3. Modlin NL, Williamson V, Goodwin GM, Malievskaia E, Atli M, Elek Z, Gaillard A, Koelpin D, Cleare A, Agrawal M et al.. (2025)
Investigational psilocybin treatment for post-traumatic stress disorder: a qualitative study of participant experience, trauma engagement, and differences from standard treatment.
EClinicalMedicine, 90: 103692. [PMID:41497513]
4. Sard H, Kumaran G, Morency C, Roth BL, Toth BA, He P, Shuster L. (2005)
SAR of psilocybin analogs: discovery of a selective 5-HT 2C agonist.
Bioorg Med Chem Lett, 15 (20): 4555-9. [PMID:16061378]