Compound Detail

CHEMBL2387541

TETRAHYDROCANNABIVARIN

🧪 Phase II

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🧪 Phase II

CCCc1cc(O)c2c(c1)OC(C)(C)[C@@H]1CCC(C)=C[C@@H]21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL2387541
Name	TETRAHYDROCANNABIVARIN
Phase	Phase II
Structure Type	MOL
InChI Key	ZROLHBHDLIHEMS-HUUCEWRRSA-N

Known Names

.delta.9-tetrahydrocannabivarin GWP-42004 Gwp42004 O-4394 Tetrahydrocannabivarin Thc-v THCV

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

286.4

MW (Da)

4.96

ALogP

HBA

HBD

29.5

PSA (Å²)

0.78

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

USAN Stem

-nab-

Extended Properties

Molecular Formula	C19H26O2
MW	286.42
Aromatic Rings	1
Heavy Atoms	21
NP-Likeness	2.36

Indications

Diabetes Mellitus, Type 2

Activity Summary

IC50 18 meas. best 7.88

EC50 13 meas. best 8.27

Ki 10 meas. best 8.82

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cannabinoid receptor 1 CHEMBL218	Ki	8.82	7.265	1.5	4
Cannabinoid receptor 2 CHEMBL253	Ki	8.55	7.5375	2.8	4
5-hydroxytryptamine receptor 1A CHEMBL273	EC50	8.27	8.27	5.4	1
Cannabinoid receptor 1 CHEMBL218	IC50	7.88	7.88	13.1	1
Cannabinoid receptor 2 CHEMBL253	IC50	7.75	7.75	17.6	1
Transient receptor potential cation channel subfamily M member 8 CHEMBL1075319	IC50	7.7	7.7	20.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	EC50	7.55	7.55	28.0	1
Cannabinoid receptor 2 CHEMBL253	EC50	7.42	7.215	38.0	2
Transient receptor potential cation channel subfamily A member 1 CHEMBL6007	EC50	7.16	6.49	70.0	2
Cannabinoid receptor 1 CHEMBL3037	Ki	7.12	7.12	75.0	2
Transient receptor potential cation channel subfamily V member 1 CHEMBL4794	EC50	6.7	6.26	200.0	2
Transient receptor potential cation channel subfamily V member 2 CHEMBL5051	IC50	6.1	6.1	800.0	1
G-protein coupled receptor 55 CHEMBL1075322	EC50	6.06	6.06	880.0	1
Transient receptor potential cation channel subfamily A member 1 CHEMBL6007	IC50	6.06	5.785	870.0	2
Transient receptor potential cation channel subfamily V member 1 CHEMBL4794	IC50	5.89	5.89	1300.0	1
Transient receptor potential cation channel subfamily V member 3 CHEMBL5522	IC50	5.52	5.52	3000.0	1
Transient receptor potential cation channel subfamily V member 4 CHEMBL3119	IC50	5.5	5.5	3200.0	1
Transient receptor potential cation channel subfamily V member 3 CHEMBL5522	EC50	5.42	5.42	3800.0	1
Transient receptor potential cation channel subfamily V member 2 CHEMBL5051	EC50	5.39	5.39	4100.0	1
Transient receptor potential cation channel subfamily V member 5 CHEMBL1628474	IC50	5.32	5.32	4800.0	1
Transient receptor potential cation channel subfamily V member 4 CHEMBL3119	EC50	5.19	5.19	6400.0	1
Transient receptor potential cation channel subfamily V member 6 CHEMBL1628465	IC50	5.03	5.03	9400.0	1
Cannabinoid receptor 1 CHEMBL3037	EC50	4.9	4.9	12700.0	1
OVCAR CHEMBL614212	IC50	4.12	4.12	75000.0	1
HepG2 CHEMBL395	IC50	4.12	4.12	75000.0	1
MCF7 CHEMBL387	IC50	4.1	4.1	80000.0	1
PC-3 CHEMBL390	IC50	4.1	4.1	79000.0	1
HCT-116 CHEMBL394	IC50	4.08	4.08	83000.0	1
A549 CHEMBL392	IC50	4.05	4.05	90000.0	1
SH-SY5Y CHEMBL614910	IC50	4.02	4.02	95000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cannabinoid receptor 1	Ki	=	1.5	nM	8.82	Displacement of [3H]-CP-55,940 from recombinant human CB1R expressed in HEK293 c...	32649196
Cannabinoid receptor 2	Ki	=	2.8	nM	8.55	Displacement of [3H]-CP-55,940 from recombinant human CB2R expressed in HEK293 c...	32649196
5-hydroxytryptamine receptor 1A	EC50	=	5.4	nM	8.27	Displacement of [35S]GTPgammaS from 5HT1A in Sprague-Dawley rat brainstem incuba...	33356248
Cannabinoid receptor 1	IC50	=	13.1	nM	7.88	Displacement of [3H]-CP-55,940 from recombinant human CB1R expressed in HEK293 c...	32649196
Cannabinoid receptor 2	IC50	=	17.6	nM	7.75	Displacement of [3H]-CP-55,940 from recombinant human CB2R expressed in HEK293 c...	32649196
Transient receptor potential cation channel subfamily M member 8	IC50	=	20.0	nM	7.7	Antagonist activity at TRPM8 (unknown origin) ion channel	33356248
5-hydroxytryptamine receptor 1A	EC50	=	28.0	nM	7.55	Displacement of [35S]GTPgammaS from 5HT1A in human CHO cells incubated for 60 mi...	33356248
Cannabinoid receptor 2	EC50	=	38.0	nM	7.42	Agonist activity at human CB2 receptor transfected in CHO cells assessed as inhi...	33356248
Cannabinoid receptor 2	Ki	=	62.8	nM	7.2	Binding affinity to CB2 receptor (unknown origin) assessed as inhibition constan...	38355400
Cannabinoid receptor 2	Ki	=	63.0	nM	7.2	Displacement of [3H]CP55940 from human CB2 receptor transfected in CHO cells ass...	33356248
Cannabinoid receptor 2	Ki	=	63.0	nM	7.2	Displacement of [3H]-CP55940 from recombinant human CB2 receptor expressed in CH...	30816712
Transient receptor potential cation channel subfamily A member 1	EC50	=	70.0	nM	7.16	Agonist activity at TRPA1 (unknown origin) ion channel	33356248
Cannabinoid receptor 1	Ki	=	75.4	nM	7.12	Binding affinity to CB1 receptor (unknown origin) assessed as inhibition constan...	38355400
Cannabinoid receptor 1	Ki	=	75.0	nM	7.12	Displacement of [3H]CP55940 from mouse brain membrane CB1 receptor assessed as i...	33356248
Cannabinoid receptor 1	Ki	=	75.4	nM	7.12	Displacement of [3H]-CP55940 from CB1 receptor in mouse whole brain membrane mea...	30816712
Cannabinoid receptor 1	Ki	=	75.4	nM	7.12	Binding affinity to human CB1 receptor	31891265
Cannabinoid receptor 2	EC50	=	98.0	nM	7.01	Agonist activity at CB2 receptor (unknown origin) expressed in CHO cell membrane...	33356248
Transient receptor potential cation channel subfamily V member 1	EC50	=	200.0	nM	6.7	Agonist activity at TRPV1 (unknown origin) ion channel	33356248
Transient receptor potential cation channel subfamily V member 2	IC50	=	800.0	nM	6.1	Agonist activity at ionomycin-stimulated TRPV2 (unknown origin) channel desensit...	33356248
G-protein coupled receptor 55	EC50	=	880.0	nM	6.06	Antagonist activity at GPR55 (unknown origin) expressed in HEK293 cells assessed...	33356248

Literature References

PubMed	DOI	Target Context	# Activities
33356248	10.1021/acs.jnatprod.0c00965	Cannabinoid receptor 2	5
33356248	10.1021/acs.jnatprod.0c00965	Transient receptor potential cation channel subfamily A member 1	5
33356248	10.1021/acs.jnatprod.0c00965	5-hydroxytryptamine receptor 1A	4
33356248	10.1021/acs.jnatprod.0c00965	Transient receptor potential cation channel subfamily V member 1	4
33356248	10.1021/acs.jnatprod.0c00965	Cannabinoid receptor 1	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
30816712	10.1021/acs.jnatprod.8b00874	Fatty-acid amide hydrolase 1	2
32649196	10.1021/acs.jnatprod.9b00831	Cannabinoid receptor 1	2
30816712	10.1021/acs.jnatprod.8b00874	RBL-2H3	2
33356248	10.1021/acs.jnatprod.0c00965	G-protein coupled receptor 55	2
30816712	10.1021/acs.jnatprod.8b00874	Diacylglycerol lipase-alpha	2
30816712	10.1021/acs.jnatprod.8b00874	Unchecked	2
30871771	10.1016/j.bmcl.2019.03.013	SH-SY5Y	2
30871771	10.1016/j.bmcl.2019.03.013	HepG2	2
30871771	10.1016/j.bmcl.2019.03.013	PC-3	2
30871771	10.1016/j.bmcl.2019.03.013	MCF7	2
30871771	10.1016/j.bmcl.2019.03.013	A549	2
30871771	10.1016/j.bmcl.2019.03.013	HCT-116	2

Data from ChEMBL 36 via Core Engine