cannabidiol   Click here for help

GtoPdb Ligand ID: 4150

Abbreviated name: CBD
Synonyms: Epidiolex® | GWP42003-P | nabiximols (CBD + THC, fixed-dose oral spray) | Sativex® (CBD + THC, fixed-dose oral spray)
Approved drug PDB Ligand
cannabidiol is an approved drug (FDA (2018), EMA (2019), UK (2019))
Compound class: Natural product or derivative
Comment: Cannabidiol (CBD) is a natural extract from Cannabis plants (a 'cannabinoid'), which has recently been approved as a much needed therapy for the treatment of orphan pediatric epilepsy syndromes. It may also have benefit in schizophrenia or post-traumatic stress disorder. The major advantage of CBD over other cannabinoids such as Δ9-tetrahydrocannabinol, is that it is devoid of psychotropic effects, whilst retaining analgesic, anti-inflammatory and other beneficial actions.
CBD is also commonly represented with the structure shown by CID 26346.
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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 0
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 40.46
Molecular weight 314.22
XLogP 6.8
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)c(c(c1)O)C1C=C(C)CCC1C(=C)C
Isomeric SMILES CCCCCc1cc(O)c(c(c1)O)[C@@H]1C=C(C)CC[C@H]1C(=C)C
InChI InChI=1S/C21H30O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3/t17-,18+/m0/s1
InChI Key QHMBSVQNZZTUGM-ZWKOTPCHSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (2018), EMA (2019), UK (2019))
IUPAC Name Click here for help
2-[(1R,6R)-3-methyl-6-prop-1-en-2-yl-1-cyclohex-2-enyl]-5-pentylbenzene-1,3-diol
International Nonproprietary Names Click here for help
INN number INN
10423 cannabidiol
Synonyms Click here for help
Epidiolex® | GWP42003-P | nabiximols (CBD + THC, fixed-dose oral spray) | Sativex® (CBD + THC, fixed-dose oral spray)
Database Links Click here for help
Specialist databases
GPCRdb Ligand cannabidiol
Other databases
CAS Registry No. 13956-29-1 (source: Scifinder)
ChEBI CHEBI:69478
ChEMBL Ligand CHEMBL190461
DrugCentral Ligand 5288
GtoPdb PubChem SID 178100971
PubChem CID 644019
RCSB PDB Ligand P0T
Search Google for chemical match using the InChIKey QHMBSVQNZZTUGM-ZWKOTPCHSA-N
Search Google for chemicals with the same backbone QHMBSVQNZZTUGM
Search PubMed clinical trials cannabidiol
Search PubMed titles cannabidiol
Search PubMed titles/abstracts cannabidiol
UniChem Compound Search for chemical match using the InChIKey QHMBSVQNZZTUGM-ZWKOTPCHSA-N
UniChem Connectivity Search for chemical match using the InChIKey QHMBSVQNZZTUGM-ZWKOTPCHSA-N
Wikipedia Cannabidiol