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
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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2D Structure
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Physico-chemical Properties
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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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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
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
LIPID MAPS LMPK13120005
PubChem CID 644019
RCSB PDB Ligand P0T
Search Google for chemical match using the InChIKey QHMBSVQNZZTUGM-ZWKOTPCHSA-N
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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