cannabidiol   Click here for help

GtoPdb Ligand ID: 4150

Abbreviated name: CBD
Synonyms: Epidiolex® | GWP42003-P | nabiximols (CBD + THC, fixed-doseoral spray) | Sativex® (CBD + THC, fixed-doseoral spray)
Approved drug PDB Ligand
cannabidiol is an approved drug (FDA (2018), EMA (2019), UK (2019))
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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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-doseoral spray) | Sativex® (CBD + THC, fixed-doseoral spray)
Database Links Click here for help
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
Search UniChem for chemical match using the InChIKey QHMBSVQNZZTUGM-ZWKOTPCHSA-N
Search UniChem for chemicals with the same backbone QHMBSVQNZZTUGM
Wikipedia Cannabidiol