CANNABIDIOL

Search structure
Trade Names:
Synonyms:
CBD
Status: Approved (2018)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: N03AX24
UNII: 19GBJ60SN5

Structure
InChI Key QHMBSVQNZZTUGM-ZWKOTPCHSA-N
Smile C=C(C)[C@@H]1CCC(C)=C[C@H]1c1c(O)cc(CCCCC)cc1O
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H30O2
Molecular Weight 314.47
AlogP 5.85
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 6.0
Polar Surface Area 40.46
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 23.0

Pharmacology

Action Mechanism of Action Reference
NEGATIVE ALLOSTERIC MODULATOR Cannabinoid CB1 receptor negative allosteric modulator PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A1
- - - 150-160 -
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- - - 2690 -
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1B Cytochrome P450 1B1
- - - 3630 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2A Cytochrome P450 2A6
- - - 55000 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2B Cytochrome P450 2B6
- - - 690 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C11
- - - 20700 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- - - 790 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- - - 5600 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- - - 2420 -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - 1000 -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A5
- - - 190 -
Enzyme Hydrolase
- 53200 - - 66
Enzyme Oxidoreductase
- - - 12300 -
Ion channel Voltage-gated ion channel Transient receptor potential channel
96-480 1100 - - -
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 100 - - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Opioid receptor
- - - 1300 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Cannabinoid receptor
- - - 1459-4350 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Lysophosphatidylinositol receptor
445 - - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- - - 3200 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- - - 2700 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- - - 3100 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
32000 - - 1100 -
Membrane receptor
32000 - - 1459-4350 -
Unclassified protein
510 750 - - 64-83

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Lennox Gastaut Syndrome 4 D065768 FDA
Epilepsies, Myoclonic 4 D004831 FDA
Amyotrophic Lateral Sclerosis 3 D000690 ClinicalTrials
Psychotic Disorders 3 D011618 ClinicalTrials
Rett Syndrome 3 D015518 ClinicalTrials
Fragile X Syndrome 3 D005600 ClinicalTrials
Spasms, Infantile 3 D013036 ClinicalTrials
Spasms, Infantile 3 D013036 ClinicalTrials
Pain 3 D010146 ClinicalTrials
Osteoarthritis 3 D010003 ClinicalTrials
Fibromyalgia 3 D005356 ClinicalTrials
Psychotic Disorders 3 D011618 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Alcoholism 2 D000437 ClinicalTrials
Hepatitis, Autoimmune 2 D019693 ClinicalTrials
Marijuana Abuse 2 D002189 ClinicalTrials
Diabetic Neuropathies 2 D003929 ClinicalTrials
Chronic Pain 2 D059350 ClinicalTrials
Arthritis, Psoriatic 2 D015535 ClinicalTrials
Huntington Disease 2 D006816 ClinicalTrials
Graft vs Host Disease 2 D006086 ClinicalTrials
Anxiety 2 D001007 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Parkinson Disease 2 D010300 ClinicalTrials
Stress Disorders, Post-Traumatic 2 D013313 ClinicalTrials
Prader-Willi Syndrome 2 D011218 ClinicalTrials
Fatty Liver 2 D005234 ClinicalTrials
Colitis, Ulcerative 2 D003093 ClinicalTrials
Cocaine-Related Disorders 2 D019970 ClinicalTrials
Opioid-Related Disorders 2 D009293 ClinicalTrials
Bipolar Disorder 2 D001714 ClinicalTrials
Tobacco Use Disorder 2 D014029 ClinicalTrials
Schizophrenia 2 D012559 ClinicalTrials
Epilepsy, Absence 2 D004832 ClinicalTrials
Graft vs Host Disease 2 D006086 ClinicalTrials
Peripheral Nervous System Diseases 2 D010523 ClinicalTrials
Child Development Disorders, Pervasive 2 D002659 ClinicalTrials
Autistic Disorder 2 D001321 ClinicalTrials
Neuralgia 2 D009437 ClinicalTrials
Opioid-Related Disorders 2 D009293 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Migraine Disorders 2 D008881 ClinicalTrials
Obsessive-Compulsive Disorder 2 D009771 ClinicalTrials
Intellectual Disability 2 D008607 ClinicalTrials
Status Epilepticus 1 D013226 ClinicalTrials
Cystitis, Interstitial 1 D018856 ClinicalTrials
Lung Neoplasms 1 D008175 ClinicalTrials
Crohn Disease 1 D003424 ClinicalTrials
Toothache 1 D014098 ClinicalTrials
Prostatic Neoplasms 1 D011471 ClinicalTrials
Radiculopathy 1 D011843 ClinicalTrials
Sturge-Weber Syndrome 1 D013341 ClinicalTrials
Heart Failure 1 D006333 ClinicalTrials
Essential Tremor 1 D020329 ClinicalTrials
Anorexia Nervosa 0 D000856 ClinicalTrials
Cognitive Dysfunction 0 D060825 ClinicalTrials

Related Entries

MCS

Cross References

Resources Reference
CAS NUMBER 13956-29-1
ChEBI 69478
ChEMBL CHEMBL190461
DrugBank DB09061
DrugCentral 5288
FDA SRS 19GBJ60SN5
Guide to Pharmacology 4150
PDB P0T
PubChem 644019
SureChEMBL SCHEMBL119679
ZINC ZINC000004097406
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