Compound Detail

CHEMBL74415

CANNABINOL

🧪 Phase III

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🧪 Phase III

CCCCCc1cc(O)c2c(c1)OC(C)(C)c1ccc(C)cc1-2

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL74415
Name	CANNABINOL
Phase	Phase III
Structure Type	MOL
InChI Key	VBGLYOIFKLUMQG-UHFFFAOYSA-N

Known Names

Cannabinol NSC-134455

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

310.4

MW (Da)

5.73

ALogP

HBA

HBD

29.5

PSA (Å²)

0.73

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

USAN Stem

-nab-

Extended Properties

Molecular Formula	C21H26O2
MW	310.44
Aromatic Rings	2
Heavy Atoms	23
NP-Likeness	1.19

Indications

Back Pain Child Development Disorders, Pervasive Chronic Pain Epilepsy Marijuana Abuse Muscle Spasticity Neck Pain Protein-Energy Malnutrition Pruritus Abdominal Pain Acquired Immunodeficiency Syndrome Amyotrophic Lateral Sclerosis Anemia, Sickle Cell Anxiety Arthritis, Psoriatic Arthritis, Rheumatoid Autistic Disorder Bipolar Disorder Brain Injuries Colitis, Ulcerative

Activity Summary

Ki 18 meas. best 7.89

IC50 17 meas. best 6.68

EC50 16 meas. best 7.14

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cannabinoid receptor 1 CHEMBL218	Ki	7.89	6.88	13.0	4
Cannabinoid receptor 2 CHEMBL253	Ki	7.8	7.08	16.0	5
Cannabinoid receptor 2 CHEMBL253	EC50	7.14	6.86	73.0	2
Cannabinoid receptor 1 CHEMBL218	EC50	7.12	7.12	75.0	1
Cytochrome P450 1A2 CHEMBL3356	Ki	7.1	7.1	79.0	1
Cannabinoid receptor 1 CHEMBL3571	EC50	6.92	6.71	120.0	2
Cytochrome P450 1B1 CHEMBL4878	Ki	6.83	6.83	148.0	1
Transient receptor potential cation channel subfamily A member 1 CHEMBL6007	EC50	6.75	6.75	180.0	1
Transient receptor potential cation channel subfamily A member 1 CHEMBL5160	EC50	6.75	6.75	180.0	1
Transient receptor potential cation channel subfamily A member 1 CHEMBL6007	IC50	6.68	6.54	210.0	2
Transient receptor potential cation channel subfamily M member 8 CHEMBL5011	IC50	6.68	6.68	210.0	1
Cannabinoid receptor 1 CHEMBL3571	Ki	6.67	6.54	211.2	2
Cytochrome P450 1A1 CHEMBL2231	Ki	6.27	6.27	541.0	1
HT-22 CHEMBL614316	EC50	6.21	6.21	610.0	1
Cytochrome P450 2A6 CHEMBL5282	Ki	6.0	6.0	1000.0	1
Cytochrome P450 2B6 CHEMBL4729	Ki	5.59	5.0	2550.0	2
Transient receptor potential cation channel subfamily V member 3 CHEMBL5522	EC50	5.28	5.28	5300.0	1
Transient receptor potential cation channel, subfamily V, member 3 CHEMBL4295541	EC50	5.28	5.28	5300.0	1
Transient receptor potential cation channel subfamily V member 4 CHEMBL3119	IC50	5.27	5.27	5400.0	1
Transient receptor potential cation channel subfamily V member 1 CHEMBL4794	EC50	5.21	5.21	6200.0	2
Transient receptor potential cation channel subfamily V member 3 CHEMBL5522	IC50	5.03	5.03	9400.0	1
Transient receptor potential cation channel subfamily V member 2 CHEMBL5051	IC50	4.8	4.8	15700.0	1
Transient receptor potential cation channel subfamily V member 4 CHEMBL2775	EC50	4.79	4.79	16100.0	1
Transient receptor potential cation channel subfamily V member 4 CHEMBL3119	EC50	4.79	4.79	16100.0	1
Transient receptor potential cation channel subfamily V member 2 CHEMBL5051	EC50	4.72	4.72	19000.0	1
Cytochrome P450 2J2 CHEMBL3491	IC50	4.72	4.72	19000.0	1
Transient receptor potential cation channel subfamily V member 2 CHEMBL2863	EC50	4.72	4.72	19000.0	1
RBL-2H3 CHEMBL614632	IC50	4.6	4.6	25000.0	1
Cytochrome P450 2A6 CHEMBL5282	IC50	4.52	4.52	30400.0	1
HepG2 CHEMBL395	IC50	4.13	4.13	74000.0	1
PC-3 CHEMBL390	IC50	4.11	4.11	78000.0	1
OVCAR CHEMBL614212	IC50	4.11	4.11	77000.0	1
HCT-116 CHEMBL394	IC50	4.1	4.1	80000.0	1
MCF7 CHEMBL387	IC50	4.09	4.09	81000.0	1
Transient receptor potential cation channel subfamily V member 1 CHEMBL4794	IC50	4.09	4.09	82000.0	1
A549 CHEMBL392	IC50	4.04	4.04	91000.0	1
SH-SY5Y CHEMBL614910	IC50	4.01	4.01	97000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cannabinoid receptor 1	Ki	=	13.0	nM	7.89	Displacement of [3H]-CP55940 from recombinant human CB1 receptor expressed in Sf...	30816712
Cannabinoid receptor 2	Ki	=	16.0	nM	7.8	Displacement of [3H]-CP55940 from recombinant human CB2 receptor expressed in Sf...	30816712
Cannabinoid receptor 1	Ki	=	70.0	nM	7.16	Binding affinity to to CB1 (unknown origin) expressed in CHO -k1 cells assessed ...	33356248
Cannabinoid receptor 2	Ki	=	70.0	nM	7.16	Binding affinity to to CB2 receptor (unknown origin) expressed in CHO -k1 cells ...	33356248
Cannabinoid receptor 2	EC50	=	73.0	nM	7.14	Displacement of 3H-CP-55940 from recombinant full length human CB2 receptor expr...	29240420
Cannabinoid receptor 1	EC50	=	75.0	nM	7.12	Displacement of 3H-CP-55940 from recombinant full length human CB1 receptor expr...	29240420
Cytochrome P450 1A2	Ki	=	79.0	nM	7.1	Competitive inhibition of human liver microsomes CYP1A2 expressed in supersomes ...	28458135
Cannabinoid receptor 2	Ki	=	96.0	nM	7.02	Binding affinity was determined for Cannabinoid receptor 2	11020293
Cannabinoid receptor 1	EC50	=	120.0	nM	6.92	Effective concentration for inhibition of Cannabinoid receptor 1-mediated adenyl...	9379442
Cannabinoid receptor 2	Ki	=	126.4	nM	6.9	Binding affinity of compound towards Cannabinoid receptor 2 in african green mon...	9379442
Cytochrome P450 1B1	Ki	=	148.0	nM	6.83	Competitive inhibition of human liver microsomes CYP1B1 expressed in supersomes ...	28458135
Transient receptor potential cation channel subfamily A member 1	EC50	=	180.0	nM	6.75	Agonist activity at TRPA1 (unknown origin) activation	33356248
Transient receptor potential cation channel subfamily A member 1	EC50	=	180.0	nM	6.75	Agonist activity at recombinant rat TRPA1 expressed in HEK293 cells assessed as ...	29240420
Transient receptor potential cation channel subfamily A member 1	IC50	=	210.0	nM	6.68	Agonist activity at TRPA1 (unknown origin) channel desensitization in presence o...	33356248
Transient receptor potential cation channel subfamily M member 8	IC50	=	210.0	nM	6.68	Antagonist activity at recombinant rat TRPM8 expressed in HEK293 cells assessed ...	29240420
Cannabinoid receptor 1	Ki	=	211.2	nM	6.67	Binding affinity of compound towards Cannabinoid receptor 1 in african green mon...	9379442
Cannabinoid receptor 2	EC50	=	261.2	nM	6.58	Effective concentration for inhibition of human Cannabinoid receptor 2-mediated ...	9379442
Cannabinoid receptor 2	Ki	=	300.0	nM	6.52	Binding affinity to to CB2 receptor (unknown origin) expressed in AtT20 cells as...	33356248
Cannabinoid receptor 1	Ki	=	308.0	nM	6.51	Binding affinity was determined for Cannabinoid receptor 1	11020293
Cannabinoid receptor 1	EC50	=	316.23	nM	6.5	Displacement of [35S]GTP-gamma-S from rat cerebellar CB1 receptor	16420041

Literature References

PubMed	DOI	Target Context	# Activities
37411021	10.1021/acs.jnatprod.3c00064	Unchecked	17
37411021	10.1021/acs.jnatprod.3c00064	Staphylococcus aureus	9
18681481	10.1021/np8002673	Staphylococcus aureus	6
33356248	10.1021/acs.jnatprod.0c00965	Transient receptor potential cation channel subfamily A member 1	4
33356248	10.1021/acs.jnatprod.0c00965	Cannabinoid receptor 2	3
33356248	10.1021/acs.jnatprod.0c00965	Transient receptor potential cation channel subfamily V member 4	3
33356248	10.1021/acs.jnatprod.0c00965	Transient receptor potential cation channel subfamily V member 3	3
33356248	10.1021/acs.jnatprod.0c00965	Transient receptor potential cation channel subfamily V member 2	3
9379442	10.1021/jm970126f	Cannabinoid receptor 1	3
33356248	10.1021/acs.jnatprod.0c00965	Transient receptor potential cation channel subfamily V member 1	3
16420041	10.1021/jm0505157	Cannabinoid receptor 1	2
29240420	10.1021/acs.jnatprod.7b00946	Cannabinoid receptor 2	2
29240420	10.1021/acs.jnatprod.7b00946	Cannabinoid receptor 1	2
30816712	10.1021/acs.jnatprod.8b00874	Unchecked	2
30871771	10.1016/j.bmcl.2019.03.013	HepG2	2
30816712	10.1021/acs.jnatprod.8b00874	N-acylethanolamine-hydrolyzing acid amidase	2
7086846	10.1021/jm00347a021	Oryctolagus cuniculus	2
30816712	10.1021/acs.jnatprod.8b00874	RBL-2H3	2
30871771	10.1016/j.bmcl.2019.03.013	SH-SY5Y	2
30816712	10.1021/acs.jnatprod.8b00874	Fatty-acid amide hydrolase 1	2

Data from ChEMBL 36 via Core Engine