Δ9-tetrahydrocannabinol   Click here for help

GtoPdb Ligand ID: 2424

Abbreviated name: THC
Synonyms: Δ9-THC | Abbott 40566 | delta9-THC | Marinol® | tetrahydrocannabinol
Approved drug PDB Ligand
Δ9-tetrahydrocannabinol is an approved drug (FDA (1985))
Compound class: Natural product
Comment: Δ9-tetrahydrocannabinol is the principle active ingredient derived from the cannabis plant (Cannabis sativa). Dronabinol is the INN for the pure, synthetically produced (-)-trans-Δ9-tetrahydrocannabinol isomer of tetrahydrocannabinol (shown here).
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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

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: delta-9-tetrahydrocannabinol

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 0
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 29.46
Molecular weight 314.22
XLogP 6.47
No. Lipinski's rules broken 1
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 CCCCCc1cc(O)c2c(c1)OC(C1C2C=C(C)CC1)(C)C
Isomeric SMILES CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2C=C(C)CC1)(C)C
InChI InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1
InChI Key CYQFCXCEBYINGO-IAGOWNOFSA-N
Classification Click here for help
Compound class Natural product
Approved drug? Yes (FDA (1985))
IUPAC Name Click here for help
(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
International Nonproprietary Names Click here for help
INN number INN
5547 dronabinol
Synonyms Click here for help
Δ9-THC | Abbott 40566 | delta9-THC | Marinol® | tetrahydrocannabinol
Database Links Click here for help
Specialist databases
GPCRdb Ligand Delta9-tetrahydrocannabinol
Other databases
BindingDB Ligand 50007391
CAS Registry No. 1972-08-3 (source: Scifinder)
ChEBI CHEBI:66964
ChEMBL Ligand CHEMBL465
DrugBank Ligand DB00470
DrugCentral Ligand 4109
GtoPdb PubChem SID 135651250
LIPID MAPS LMPK13120004
PubChem CID 16078
RCSB PDB Ligand TCI
Search Google for chemical match using the InChIKey CYQFCXCEBYINGO-IAGOWNOFSA-N
Search Google for chemicals with the same backbone CYQFCXCEBYINGO
Search PubMed clinical trials dronabinol
Search PubMed titles dronabinol
Search PubMed titles/abstracts dronabinol
UniChem Compound Search for chemical match using the InChIKey CYQFCXCEBYINGO-IAGOWNOFSA-N
UniChem Connectivity Search for chemical match using the InChIKey CYQFCXCEBYINGO-IAGOWNOFSA-N
Wikipedia Tetrahydrocannabinol