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Compound Detail

CHEMBL422704

CANNABICHROMENE
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CCCCCc1cc(O)c2c(c1)OC(C)(CCC=C(C)C)C=C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL422704
Name CANNABICHROMENE
Phase Preclinical
Structure Type MOL
InChI Key UVOLYTDXHDXWJU-UHFFFAOYSA-N
19
Targets
26
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

314.5
MW (Da)
6.04
ALogP
2
HBA
1
HBD
29.5
PSA (Ų)
0.49
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H30O2
MW 314.47
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness 2.91

Activity Summary

IC50 14 meas. best 6.43
EC50 7 meas. best 7.22
Ki 5 meas. best 6.59

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Transient receptor potential cation channel subfamily A member 1
CHEMBL5160
 EC50 7.22 6.2433 60.0 3
Transient receptor potential cation channel subfamily A member 1
CHEMBL6007
 EC50 7.05 7.05 90.0 1
Cannabinoid receptor 2
CHEMBL253
 Ki 6.59 6.585 257.0 2
Transient receptor potential cation channel subfamily A member 1
CHEMBL6007
 IC50 6.43 6.43 370.0 1
Transient receptor potential cation channel subfamily V member 4
CHEMBL3119
 EC50 6.22 6.22 600.0 1
Cannabinoid receptor 1
CHEMBL218
 Ki 6.15 6.15 710.0 2
Transient receptor potential cation channel subfamily V member 3
CHEMBL5522
 EC50 5.72 5.72 1900.0 1
Transient receptor potential cation channel subfamily V member 2
CHEMBL5051
 IC50 5.19 5.19 6500.0 1
L-lactate dehydrogenase A chain
CHEMBL4835
 Ki 5.07 5.07 8500.0 1
Transient receptor potential cation channel subfamily V member 4
CHEMBL3119
 IC50 5.0 5.0 9900.0 1
RBL-2H3
CHEMBL614632
 IC50 4.91 4.91 12300.0 1
Transient receptor potential cation channel subfamily V member 1
CHEMBL4794
 EC50 4.62 4.62 24200.0 1
PC-3
CHEMBL390
 IC50 4.4 4.4 40000.0 1
MCF7
CHEMBL387
 IC50 4.4 4.4 40000.0 1
Transient receptor potential cation channel subfamily M member 8
CHEMBL1075319
 IC50 4.39 4.39 40700.0 1
Unchecked
CHEMBL612545
 IC50 4.3 4.3 50100.0 1
HepG2
CHEMBL395
 IC50 4.22 4.22 60000.0 1
HCT-116
CHEMBL394
 IC50 4.22 4.22 60000.0 1
A549
CHEMBL392
 IC50 4.22 4.22 60000.0 1
OVCAR
CHEMBL614212
 IC50 4.19 4.19 65000.0 1
SH-SY5Y
CHEMBL614910
 IC50 4.11 4.11 77000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Transient receptor potential cation channel subfamily A member 1 EC50 = 60.0 nM 7.22 Agonist activity at rat TRPA1 channel expressed in HEK293 cells assessed as incr... 20356305
Transient receptor potential cation channel subfamily A member 1 EC50 = 90.0 nM 7.05 Agonist activity at TRPA1 (unknown origin) activation 33356248
Transient receptor potential cation channel subfamily A member 1 EC50 = 90.0 nM 7.05 Agonist activity at rat TRPA1 expressed in HEK293 cells 38158562
Cannabinoid receptor 2 Ki = 257.0 nM 6.59 Displacement of [3H]-CP55940 from recombinant human CB2 receptor expressed in Sf... 30816712
Cannabinoid receptor 2 Ki = 260.0 nM 6.58 Displacement of [3H]CP55940 from human CB2 receptor expressed in Sf9 cell membra... 38158562
Transient receptor potential cation channel subfamily A member 1 IC50 = 370.0 nM 6.43 Agonist activity at TRPA1 (unknown origin) channel desensitization in presence o... 33356248
Transient receptor potential cation channel subfamily V member 4 EC50 = 600.0 nM 6.22 Agonist activity at ionomycin-stimulated TRPV4 (unknown origin) activation 33356248
Cannabinoid receptor 1 Ki = 710.0 nM 6.15 Displacement of [3H]CP55940 from human CB1 receptor expressed in Sf9 cell membra... 38158562
Cannabinoid receptor 1 Ki = 714.0 nM 6.15 Displacement of [3H]-CP55940 from recombinant human CB1 receptor expressed in Sf... 30816712
Transient receptor potential cation channel subfamily V member 3 EC50 = 1900.0 nM 5.72 Agonist activity at ionomycin-stimulated TRPV3 (unknown origin) activation 33356248
Transient receptor potential cation channel subfamily V member 2 IC50 = 6500.0 nM 5.19 Agonist activity at ionomycin-stimulated TRPV2 (unknown origin) channel desensit... 33356248
L-lactate dehydrogenase A chain Ki = 8500.0 nM 5.07 Non-competitive inhibition of human LDHA assessed as reduction in lactate produc... 33887133
Transient receptor potential cation channel subfamily V member 4 IC50 = 9900.0 nM 5.0 Agonist activity at ionomycin-stimulated TRPV4 (unknown origin) channel desensit... 33356248
RBL-2H3 IC50 = 12300.0 nM 4.91 Inhibition of [14C]-AEA uptake in rat RBL2H3 cells by scintillation counting met... 30816712
Transient receptor potential cation channel subfamily V member 1 EC50 = 24200.0 nM 4.62 Agonist activity at ionomycin-stimulated TRPV1 (unknown origin) activation 33356248
Transient receptor potential cation channel subfamily A member 1 EC50 = 34300.0 nM 4.46 Agonist activity at TRPA1 channel in rat DRG neurons assessed as increase in int... 20356305
PC-3 IC50 = 40000.0 nM 4.4 Cytotoxicity against human PC3 cells assessed as reduction in cell viability inc... 30871771
MCF7 IC50 = 40000.0 nM 4.4 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability in... 30871771
Transient receptor potential cation channel subfamily M member 8 IC50 = 40700.0 nM 4.39 Antagonist activity at TRPM8 (unknown origin) ion channel 33356248
Unchecked IC50 = 50100.0 nM 4.3 Inhibition of MAGL in African green monkey COS cell homogenates using [3H]-arach... 30816712

Literature References

PubMed DOI Target Context # Activities
38477310 10.1021/acs.jnatprod.3c00336 ADMET 14
38477310 10.1021/acs.jnatprod.3c00336 Cytochrome P450 3A4 9
38477310 10.1021/acs.jnatprod.3c00336 Cytochrome P450 2J2 9
38477310 10.1021/acs.jnatprod.3c00336 Cytochrome P450 2C8 9
38477310 10.1021/acs.jnatprod.3c00336 Cytochrome P450 2D6 8
37402317 10.1021/acs.jnatprod.3c00111 SARS-CoV-2 7
18681481 10.1021/np8002673 Staphylococcus aureus 6
38477310 10.1021/acs.jnatprod.3c00336 Cytochrome P450 2C9 5
33356248 10.1021/acs.jnatprod.0c00965 Transient receptor potential cation channel subfamily A member 1 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 4 3
33356248 10.1021/acs.jnatprod.0c00965 Transient receptor potential cation channel subfamily V member 1 3
7086846 10.1021/jm00347a021 Oryctolagus cuniculus 3
30871771 10.1016/j.bmcl.2019.03.013 A549 2
30871771 10.1016/j.bmcl.2019.03.013 OVCAR 2
30871771 10.1016/j.bmcl.2019.03.013 PC-3 2
30871771 10.1016/j.bmcl.2019.03.013 HepG2 2
30816712 10.1021/acs.jnatprod.8b00874 Fatty-acid amide hydrolase 1 2
30816712 10.1021/acs.jnatprod.8b00874 Unchecked 2
30816712 10.1021/acs.jnatprod.8b00874 Diacylglycerol lipase-alpha 2

Data from ChEMBL 36 via Core Engine