Compound Detail

CHEMBL465718

DELTA9-TETRAHYDROCANNABINOLIC ACID A

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CCCCCc1cc2c(c(O)c1C(=O)O)[C@@H]1C=C(C)CC[C@H]1C(C)(C)O2

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL465718
Name	DELTA9-TETRAHYDROCANNABINOLIC ACID A
Phase	Preclinical
Structure Type	MOL
InChI Key	UCONUSSAWGCZMV-HZPDHXFCSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

358.5

MW (Da)

5.43

ALogP

HBA

HBD

66.8

PSA (Å²)

0.54

QED

Ro5 Violations

Rot. Bonds

Natural Product First in Class Prodrug

IC50 4 meas. best 6.82

Ki 3 meas. best 7.62

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cannabinoid receptor 1 CHEMBL218	Ki	7.62	7.62	24.0	1
Cannabinoid receptor 2 CHEMBL253	Ki	7.25	7.25	56.0	1
Transient receptor potential cation channel subfamily M member 8 CHEMBL1075319	IC50	6.82	6.82	150.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	IC50	6.33	6.33	470.0	1
L-lactate dehydrogenase A chain CHEMBL4835	Ki	5.19	5.19	6500.0	1
Diacylglycerol lipase-alpha CHEMBL5545	IC50	4.56	4.56	27300.0	1
Unchecked CHEMBL612545	IC50	4.34	4.34	46000.0	1

Parameter	Value	Units	Species
AUC	5033.33	ng.hr.mL-1	Mus musculus
AUC	5033.33	ng.hr.mL-1	Mus musculus
AUC	5633.33	ng.hr.mL-1	Mus musculus
Cmax	7810.76	nM	Mus musculus
Cmax	7810.76	nM	Mus musculus
Cmax	19247.94	nM	Mus musculus
Cmax	-	-	Mus musculus
Cmax	-	-	Mus musculus
Cmax	-	-	Mus musculus
T1/2	1.117	hr	Mus musculus
T1/2	1.117	hr	Mus musculus
T1/2	0.55	hr	Mus musculus
Tmax	0.25	hr	Mus musculus
Tmax	0.25	hr	Mus musculus
Tmax	0.25	hr	Mus musculus

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cannabinoid receptor 1	Ki	=	24.0	nM	7.62	Displacement of [3H]-CP55940 from recombinant human CB1 receptor expressed in Sf...	30816712
Cannabinoid receptor 2	Ki	=	56.0	nM	7.25	Displacement of [3H]-CP55940 from recombinant human CB2 receptor expressed in Sf...	30816712
Transient receptor potential cation channel subfamily M member 8	IC50	=	150.0	nM	6.82	Antagonist activity at TRPM8 (unknown origin)	27437828
Peroxisome proliferator-activated receptor gamma	IC50	=	470.0	nM	6.33	Agonist activity at PPARgamma (unknown origin)	33992930
L-lactate dehydrogenase A chain	Ki	=	6500.0	nM	5.19	Non-competitive inhibition of human LDHA assessed as reduction in lactate produc...	33887133
Diacylglycerol lipase-alpha	IC50	=	27300.0	nM	4.56	Inhibition of recombinant human DAGLalpha expressed in COS7 cells using [14C]-ol...	30816712
Unchecked	IC50	=	46000.0	nM	4.34	Inhibition of MAGL in African green monkey COS cell homogenates using [3H]-arach...	30816712

PubMed	DOI	Target Context	# Activities
31686510	10.1021/acs.jnatprod.9b00600	ADMET	19
18681481	10.1021/np8002673	Staphylococcus aureus	6
31686510	10.1021/acs.jnatprod.9b00600	No relevant target	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
30816712	10.1021/acs.jnatprod.8b00874	N-acylethanolamine-hydrolyzing acid amidase	2
30816712	10.1021/acs.jnatprod.8b00874	RBL-2H3	2
33887133	10.1021/acs.jnatprod.0c01281	L-lactate dehydrogenase A chain	2
33992930	10.1016/j.ejmech.2021.113535	Peroxisome proliferator-activated receptor gamma	2
18303850	10.1021/np070454a	Cannabinoid receptor 1	1
30816712	10.1021/acs.jnatprod.8b00874	Cannabinoid receptor 2	1
30816712	10.1021/acs.jnatprod.8b00874	Cannabinoid receptor 1	1
33887133	10.1021/acs.jnatprod.0c01281	L-lactate dehydrogenase B chain	1
27437828	10.1021/acs.jmedchem.6b00305	Transient receptor potential cation channel subfamily M member 8	1

Data from ChEMBL 36 via Core Engine