Compound Detail

CHEMBL190461

CANNABIDIOL

💊 Approved Drug

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💊 Approved Drug

C=C(C)[C@@H]1CCC(C)=C[C@H]1c1c(O)cc(CCCCC)cc1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL190461
Name	CANNABIDIOL
Phase	Approved
Structure Type	MOL
InChI Key	QHMBSVQNZZTUGM-ZWKOTPCHSA-N
Therapeutic	✓ Yes

Known Names

(-)-cannabidiol (-)-cbd (-)-trans-cannabidiol .delta.1(2)-trans-cannabidiol BTX-1204 BTX-1503 Cannabidiol Cannabidiol solution Cardiolrx Epidiolex Epidyolex GWP-42003 +3 more

Targets

128

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

314.5

MW (Da)

5.85

ALogP

HBA

HBD

40.5

PSA (Å²)

0.51

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2018
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product

USAN Stem	-nab-
USAN Year	2016

Extended Properties

Molecular Formula	C21H30O2
MW	314.47
Aromatic Rings	1
Heavy Atoms	23
NP-Likeness	1.98

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Cannabinoid CB1 receptor negative allosteric modulator	NEGATIVE ALLOSTERIC MODULATOR	Cannabinoid receptor 1	✓	✓

Indications

Epilepsies, Myoclonic Epilepsy Lennox Gastaut Syndrome Seizures Tuberous Sclerosis Amyotrophic Lateral Sclerosis Bipolar Disorder Breast Neoplasms Fibromyalgia Fragile X Syndrome Motor Neuron Disease Osteoarthritis, Knee Pain Psychotic Disorders Psychotic Disorders Rett Syndrome Sleep Initiation and Maintenance Disorders Spasms, Infantile Spasms, Infantile Alcoholism

ATC Classification

N03AX24

cannabidiol

Level 1: NERVOUS SYSTEM

Level 2: ANTIEPILEPTICS

Activity Summary

IC50 47 meas. best 9.35

EC50 43 meas. best 8.1

Ki 36 meas. best 6.82

Kd 2 meas. best 7.73

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Neutrophil CHEMBL613710	IC50	9.35	9.35	0.5	1
Cannabinoid receptor 2 CHEMBL253	EC50	8.1	7.2324	7.9	21
Caspase-1 CHEMBL4801	Kd	7.73	7.73	18.8	1
Transient receptor potential cation channel subfamily M member 8 CHEMBL1075319	IC50	7.22	7.22	60.0	1
Transient receptor potential cation channel subfamily A member 1 CHEMBL5160	EC50	7.02	6.67	96.0	2
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL3762	IC50	7.0	7.0	100.0	1
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A CHEMBL3535	IC50	6.96	6.96	110.0	1
Gamma-aminobutyric acid receptor subunit beta-2 CHEMBL1920	IC50	6.89	6.89	130.0	1
Cannabinoid receptor 1 CHEMBL218	Ki	6.82	5.8	151.0	5
Cytochrome P450 1A1 CHEMBL2231	Ki	6.82	6.81	150.0	2
Cytochrome P450 3A5 CHEMBL3019	Ki	6.72	6.72	190.0	1
Cannabinoid receptor 2 CHEMBL5373	Ki	6.64	6.64	230.0	1
Calcium-activated potassium channel subunit alpha-1 CHEMBL4304	IC50	6.55	6.55	280.0	1
Mu-type opioid receptor CHEMBL233	IC50	6.51	6.13	311.0	2
Cannabinoid receptor 2 CHEMBL253	Ki	6.43	5.57	372.0	5
Transient receptor potential cation channel subfamily A member 1 CHEMBL5160	IC50	6.35	6.35	450.0	1
G-protein coupled receptor 55 CHEMBL1075322	EC50	6.35	6.35	445.0	1
Heat sensitive channel TRPV3 CHEMBL3879847	EC50	6.29	6.29	510.0	1
Cholinesterase CHEMBL5763	IC50	6.17	6.17	670.0	1
Cytochrome P450 2B6 CHEMBL4729	Ki	6.16	6.16	690.0	1
Heat sensitive channel TRPV3 CHEMBL3879847	IC50	6.12	6.12	750.0	1
Cytochrome P450 2C19 CHEMBL3622	Ki	6.1	6.1	790.0	1
PWR-1E CHEMBL4296487	IC50	6.05	6.05	900.0	1
Transient receptor potential cation channel subfamily V member 4 CHEMBL2775	EC50	6.05	6.05	900.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	6.0	5.655	1000.0	4
Cytochrome P450 3A4 CHEMBL340	Ki	6.0	6.0	1000.0	1
RWPE-1 CHEMBL4296492	IC50	5.96	5.96	1100.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	5.96	5.96	1100.0	1
Transient receptor potential cation channel subfamily V member 2 CHEMBL2863	IC50	5.96	5.96	1100.0	1
Transient receptor potential cation channel subfamily V member 2 CHEMBL2863	EC50	5.92	5.92	1200.0	1
Cannabinoid receptor 1 CHEMBL3571	Ki	5.9	5.9	1265.0	1
Mu-type opioid receptor CHEMBL233	Ki	5.89	5.89	1300.0	1
Cannabinoid receptor 1 CHEMBL218	EC50	5.83	5.83	1469.0	1
DU-145 CHEMBL613508	IC50	5.82	5.3333	1500.0	3
4T1 CHEMBL612589	IC50	5.75	5.75	1800.0	1
Kappa-type opioid receptor CHEMBL237	Ki	5.64	5.64	2300.0	1
Cytochrome P450 2D6 CHEMBL289	Ki	5.62	5.62	2420.0	1
LNCaP CHEMBL612518	IC50	5.58	5.165	2600.0	2
Glycine receptor subunit alpha-2 CHEMBL5871	IC50	5.57	5.57	2700.0	1
D(1A) dopamine receptor CHEMBL2056	Ki	5.57	5.57	2700.0	1
Cytochrome P450 1A2 CHEMBL3356	Ki	5.57	5.57	2690.0	1
Transient receptor potential cation channel subfamily M member 8 CHEMBL5011	IC50	5.55	5.55	2800.0	1
PC-3 CHEMBL390	IC50	5.54	5.1467	2900.0	3
Histamine H3 receptor CHEMBL264	Ki	5.51	5.51	3100.0	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	5.5	5.5	3200.0	1
Sigma intracellular receptor 2 CHEMBL4105907	Ki	5.47	5.47	3400.0	1
Cytochrome P450 1B1 CHEMBL4878	Ki	5.44	5.44	3630.0	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	5.43	5.43	3700.0	1
Unchecked CHEMBL612545	EC50	5.43	5.43	3700.0	1
Caco-2 CHEMBL614058	IC50	5.43	5.43	3730.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	4655.0	ng.hr.mL-1	Mus musculus
AUC	4872.0	ng.hr.mL-1	Mus musculus
AUC	9463.0	ng.hr.mL-1	Rattus norvegicus
AUC	10151.0	ng.hr.mL-1	Rattus norvegicus
AUC	289.0	ng.hr.mL-1	Mus musculus
CL	389.5	mL.min-1.kg-1	Homo sapiens
CL	4903.66	mL.min-1.kg-1	Rattus norvegicus
CL	1721.52	mL.min-1.kg-1	Mus musculus
CL	250.0	mL.min-1.kg-1	Mus musculus
CL	123.33	mL.min-1.kg-1	Rattus norvegicus
Cmax	0.9	nM	Homo sapiens
Cmax	41.5	nM	Homo sapiens
Cmax	11.1	nM	Homo sapiens
Cmax	4000.0	nM	Mus musculus
Cmax	1000.0	nM	Mus musculus
Cmax	2127.39	nM	Mus musculus
Cmax	2315.01	nM	Rattus norvegicus
Cmax	98.1	ng/g	Mus musculus
Cmax	461.09	nM	Mus musculus
Cmax	239.0	ng/g	Mus musculus
F	31.0	%	Homo sapiens
F	13.0	%	Canis lupus familiaris
F	24.0	%	Mus musculus
Ka	415.5	1/Ms	Homo sapiens
MRT	0.7	hr	Mus musculus
T1/2	2.0	hr	Homo sapiens
T1/2	2.0	hr	Homo sapiens
T1/2	2.0	hr	Homo sapiens
T1/2	24.0	hr	Homo sapiens
T1/2	31.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Neutrophil	IC50	=	0.45	nM	9.35	Inhibition of human neutrophil migration incubated for 30 mins prior to fMLP cha...	25703248
Cannabinoid receptor 2	EC50	=	7.943	nM	8.1	Partial agonist activity at wild type CB2 receptor (unknown origin) expressed in...	34161090
Cannabinoid receptor 2	EC50	=	7.943	nM	8.1	Partial agonist activity at CBR2 A2827.36M mutant (unknown origin) stably expres...	34161090
Cannabinoid receptor 2	EC50	=	12.59	nM	7.9	Partial agonist activity at wild type CB2 receptor (unknown origin) expressed in...	34161090
Cannabinoid receptor 2	EC50	=	12.59	nM	7.9	Partial agonist activity at CBR2 V1133.32M mutant (unknown origin) expressed in ...	34161090
Cannabinoid receptor 2	EC50	=	12.59	nM	7.9	Partial agonist activity at CBR2 A2827.36M mutant (unknown origin) expressed in ...	34161090
Cannabinoid receptor 2	EC50	=	15.85	nM	7.8	Partial agonist activity at CBR2 V361.35M mutant (unknown origin) stably express...	34161090
Caspase-1	Kd	=	18.8	nM	7.73	Binding affinity to recombinant human caspase-1 assessed as dissociation constan...	33955754
Cannabinoid receptor 2	EC50	=	25.12	nM	7.6	Partial agonist activity at CBR2 V1133.32M mutant (unknown origin) stably expres...	34161090
Cannabinoid receptor 2	EC50	=	31.62	nM	7.5	Partial agonist activity at CBR2 S2857.39L mutant (unknown origin) expressed in ...	34161090
Cannabinoid receptor 2	EC50	=	39.81	nM	7.4	Partial agonist activity at CBR2 S2857.39L mutant (unknown origin) stably expres...	34161090
Cannabinoid receptor 2	EC50	=	39.81	nM	7.4	Partial agonist activity at CBR2 V1133.32M mutant (unknown origin) stably expres...	34161090
Cannabinoid receptor 2	EC50	=	39.81	nM	7.4	Partial agonist activity at CBR2 V1133.32M mutant (unknown origin) expressed in ...	34161090
Cannabinoid receptor 2	EC50	=	39.81	nM	7.4	Partial agonist activity at CBR2 V361.35M mutant (unknown origin) expressed in H...	34161090
Cannabinoid receptor 2	EC50	=	50.12	nM	7.3	Partial agonist activity at wild type CB2 receptor (unknown origin) stably expre...	34161090
Cannabinoid receptor 2	EC50	=	50.12	nM	7.3	Partial agonist activity at wild type CB2 receptor (unknown origin) stably expre...	34161090
Transient receptor potential cation channel subfamily M member 8	IC50	=	60.0	nM	7.22	Antagonist activity at TRPM8 (unknown origin)	27437828
Transient receptor potential cation channel subfamily A member 1	EC50	=	96.0	nM	7.02	Agonist activity at rat TRPA1 channel expressed in HEK293 cells assessed as incr...	20356305
Voltage-dependent L-type calcium channel subunit alpha-1C	IC50	=	100.0	nM	7.0	Inhibition of Cav1.2 calcium current measured using whole cell patch clamp in ra...	-
Cannabinoid receptor 2	EC50	=	104.0	nM	6.98	Agonist activity at CB2 receptor (unknown origin)	39038276

Literature References

PubMed	DOI	Target Context	# Activities
34161090	10.1021/acs.jmedchem.1c00561	Cannabinoid receptor 2	45
32804502	10.1021/acs.jmedchem.0c00724	ADMET	28
37703852	10.1021/acs.jnatprod.3c00363	PC-3	24
38603577	10.1021/acs.jnatprod.3c00782	A2780	22
37703852	10.1021/acs.jnatprod.3c00363	DU-145	20
38373879	10.1021/acs.jnatprod.3c00759	HaCaT	19
33955754	10.1021/acs.jnatprod.1c00083	HaCaT	19
38708937	10.1021/acs.jnatprod.3c01274	Calcium-activated potassium channel subunit alpha-1	15
37411021	10.1021/acs.jnatprod.3c00064	Unchecked	14
38603577	10.1021/acs.jnatprod.3c00782	Unchecked	14
38352838	10.1021/acsmedchemlett.3c00461	ADMET	13
32374168	10.1021/acs.jnatprod.0c00138	THP-1	11
38603577	10.1021/acs.jnatprod.3c00782	ES-2	10
37411021	10.1021/acs.jnatprod.3c00064	Staphylococcus aureus	9
2989518	10.1021/jm00383a016	Mus musculus	8
37437224	10.1021/acs.jmedchem.3c00061	Mu-type opioid receptor	8
38373879	10.1021/acs.jnatprod.3c00759	Unchecked	7
37402317	10.1021/acs.jnatprod.3c00111	SARS-CoV-2	7
37703852	10.1021/acs.jnatprod.3c00363	PWR-1E	7
18681481	10.1021/np8002673	Staphylococcus aureus	6

Data from ChEMBL 36 via Core Engine