CHEBI:69478 - cannabidiol

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ChEBI Name cannabidiol
ChEBI ID CHEBI:69478
Definition An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3358
Supplier Information ChemicalBook:CB7673434, eMolecules:536311, ZINC000004097406
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Wikipedia License
Cannabidiol (CBD) is a phytocannabinoid, one of 113 identified cannabinoids in cannabis plants, along with tetrahydrocannabinol (THC), and accounts for up to 40% of the plant's extract. Medically, it is an anticonvulsant used to treat multiple forms of epilepsy. It was discovered in 1940 and, as of 2024 clinical research on CBD included studies related to the treatment of anxiety, addiction, psychosis, movement disorders, and pain, but there is insufficient high-quality evidence that CBD is effective for these conditions. CBD is sold as an herbal dietary supplement and promoted with yet unproven claims of particular therapeutic effects. Cannabidiol can be taken internally in multiple ways, including by inhaling cannabis smoke or vapor, swallowing it by mouth, and through use of an aerosol spray into the cheek. It may be supplied as CBD oil containing only CBD as the active ingredient (excluding THC or terpenes), CBD-dominant hemp extract oil, capsules, dried cannabis, or prescription liquid solution. CBD does not have the same psychoactivity as THC, and can modulate the psychoactive effects of THC on the body if both are present. Conversion of CBD to THC can occur when CBD is heated to temperatures between 250–300 °C, potentially leading to its partial transformation into THC. In the United States, the cannabidiol drug Epidiolex was approved by the Food and Drug Administration (FDA) in 2018 for the treatment of two seizure disorders. While the 2018 United States Farm Bill removed hemp and hemp extracts (including CBD) from the Controlled Substances Act, the marketing and sale of CBD formulations for medical use or as an ingredient in dietary supplements or manufactured foods remains illegal under FDA regulation, as of 2024.
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Formula C21H30O2
Net Charge 0
Average Mass 314.469
Monoisotopic Mass 314.22458
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
InChIKey QHMBSVQNZZTUGM-ZWKOTPCHSA-N
SMILES [H][C@]1(CCC(C)=C[C@H]1C1=C(O)C=C(CCCCC)C=C1O)C(C)=C
Metabolite of Species Details
Cannabis sativa (NCBI:txid3483) Found in aerial part (BTO:0001658). Acetone extract of Dried, powdered and heated flowered aerial parts See: PubMed
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via phytocannabinoid )
cannabinoid receptor agonist
An agonist that binds to and activates cannabinoid receptors.
(via cannabinoid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cannabidiol (CHEBI:69478) has role antimicrobial agent (CHEBI:33281)
cannabidiol (CHEBI:69478) has role plant metabolite (CHEBI:76924)
cannabidiol (CHEBI:69478) is a olefinic compound (CHEBI:78840)
cannabidiol (CHEBI:69478) is a phytocannabinoid (CHEBI:67196)
cannabidiol (CHEBI:69478) is a resorcinols (CHEBI:33572)
Incoming hydroxy-cannabidiol (CHEBI:133048) has functional parent cannabidiol (CHEBI:69478)
IUPAC Name
(1'R,2'R)-5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydrobiphenyl-2,6-diol
INNs Sources
cannabidiol WHO MedNet
cannabidiol WHO MedNet
cannabidiol WHO MedNet
cannabidiolum WHO MedNet
Synonyms Sources
(−)-cannabidiol ChemIDplus
(−)-CBD ChemIDplus
(−)-trans-2-p-mentha-1,8-dien-3-yl-5-pentylresorcinol ChemIDplus
(−)-trans-cannabidiol ChemIDplus
Δ1(2)-trans-cannabidiol ChemIDplus
Manual Xrefs Databases
5288 DrugCentral
C00002641 KNApSAcK
C07578 KEGG COMPOUND
Cannabidiol Wikipedia
CPD-7173 MetaCyc
DB09061 DrugBank
LMPK13120001 LIPID MAPS
P0T PDBeChem
US2304669 Patent
View more database links
Registry Numbers Types Sources
13956-29-1 CAS Registry Number KEGG COMPOUND
13956-29-1 CAS Registry Number ChemIDplus
13956-29-1 CAS Registry Number NIST Chemistry WebBook
2222023 Reaxys Registry Number Reaxys
Citations
Fitzcharles MA, Clauw DJ, Häuser W (2023)
Cautious Hope for Cannabidiol (CBD) in Rheumatology Care.
Arthritis care & research 75, 1371-1375 [PubMed:32144889]
[show Abstract]
Alvarez JC, Pelissier AL, Mura P, Goullé JP (2023)
[Cannabidiol (CBD): Analytical and toxicological aspects].
Therapie 78, 639-645 [PubMed:36868996]
[show Abstract]
Pumroy RA, Samanta A, Liu Y, Hughes TE, Zhao S, Yudin Y, Rohacs T, Han S, Moiseenkova-Bell VY (2019)
Molecular mechanism of TRPV2 channel modulation by cannabidiol.
eLife 8, e48792 [PubMed:31566564]
[show Abstract]
Karl T, Garner B, Cheng D (2017)
The therapeutic potential of the phytocannabinoid cannabidiol for Alzheimer's disease.
Behavioural pharmacology 28, 142-160 [PubMed:27471947]
[show Abstract]
Reddy DS (2017)
The Utility of Cannabidiol in the Treatment of Refractory Epilepsy.
Clinical pharmacology and therapeutics 101, 182-184 [PubMed:27506704]
[show Abstract]
Soares VP, Campos AC (2017)
Evidences for the Anti-panic Actions of Cannabidiol.
Current neuropharmacology 15, 291-299 [PubMed:27157263]
[show Abstract]
Rajan TS, Giacoppo S, Iori R, De Nicola GR, Grassi G, Pollastro F, Bramanti P, Mazzon E (2016)
Anti-inflammatory and antioxidant effects of a combination of cannabidiol and moringin in LPS-stimulated macrophages.
Fitoterapia 112, 104-115 [PubMed:27215129]
[show Abstract]
Heinl S, Lerch O, Erdmann F (2016)
Automated GC-MS Determination of Δ9-Tetrahydrocannabinol, Cannabinol and Cannabidiol in Hair.
Journal of analytical toxicology 40, 498-503 [PubMed:27344041]
[show Abstract]
Fakhoury M (2016)
Could cannabidiol be used as an alternative to antipsychotics?
Journal of psychiatric research 80, 14-21 [PubMed:27267317]
[show Abstract]
Parray HA, Yun JW (2016)
Cannabidiol promotes browning in 3T3-L1 adipocytes.
Molecular and cellular biochemistry 416, 131-139 [PubMed:27067870]
[show Abstract]
Chen J, Hou C, Chen X, Wang D, Yang P, He X, Zhou J, Li H (2016)
Protective effect of cannabidiol on hydrogen peroxide‑induced apoptosis, inflammation and oxidative stress in nucleus pulposus cells.
Molecular medicine reports 14, 2321-2327 [PubMed:27430346]
[show Abstract]
Leo A, Russo E, Elia M (2016)
Cannabidiol and epilepsy: Rationale and therapeutic potential.
Pharmacological research 107, 85-92 [PubMed:26976797]
[show Abstract]
Campos AC, Fogaça MV, Sonego AB, Guimarães FS (2016)
Cannabidiol, neuroprotection and neuropsychiatric disorders.
Pharmacological research 112, 119-127 [PubMed:26845349]
[show Abstract]
Fasinu PS, Phillips S, ElSohly MA, Walker LA (2016)
Current Status and Prospects for Cannabidiol Preparations as New Therapeutic Agents.
Pharmacotherapy 36, 781-796 [PubMed:27285147]
[show Abstract]
Gururajan A, Malone DT (2016)
Does cannabidiol have a role in the treatment of schizophrenia?
Schizophrenia research 176, 281-290 [PubMed:27374322]
[show Abstract]
Burstein S (2015)
Cannabidiol (CBD) and its analogs: a review of their effects on inflammation.
Bioorganic & medicinal chemistry 23, 1377-1385 [PubMed:25703248]
[show Abstract]
Last Modified
07 June 2023