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Compound Detail

CHEMBL498672

CANNABIDIOLIC ACID
🧪 Phase II
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🧪 Phase II
C=C(C)[C@@H]1CCC(C)=C[C@H]1c1c(O)cc(CCCCC)c(C(=O)O)c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL498672
Name CANNABIDIOLIC ACID
Phase Phase II
Structure Type MOL
InChI Key WVOLTBSCXRRQFR-DLBZAZTESA-N

Known Names

Cannabidiol acid Cannabidiolic acid
5
Targets
11
Activities
2
Assay Types
24
PK Parameters
20
Publications
2
Known Names

Molecular Properties

358.5
MW (Da)
5.54
ALogP
3
HBA
3
HBD
77.8
PSA (Ų)
0.44
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -nab-

Extended Properties

Molecular Formula C22H30O4
MW 358.48
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness 2.26

Activity Summary

IC50 10 meas. best 4.71
EC50 1 meas. best 4.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Transient receptor potential cation channel subfamily A member 1
CHEMBL5160
 EC50 4.92 4.92 12000.0 1
Diacylglycerol lipase-alpha
CHEMBL5545
 IC50 4.71 4.71 19400.0 1
N-acylethanolamine-hydrolyzing acid amidase
CHEMBL4349
 IC50 4.64 4.64 23000.0 1
SARS-CoV-2
CHEMBL4303835
 IC50 4.51 4.4029 30700.0 7
Unchecked
CHEMBL612545
 IC50 4.33 4.33 47000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 78316.67 ng.hr.mL-1 Mus musculus
AUC 183.0 ng.min/g Mus musculus
AUC 78316.67 ng.hr.mL-1 Mus musculus
AUC 183.0 ng.min/g Mus musculus
AUC 9966.67 ng.hr.mL-1 Mus musculus
AUC 1142.0 ng.min/g Mus musculus
Cmax 82570.85 nM Mus musculus
Cmax 2.0 ng/mg Mus musculus
Cmax 82570.85 nM Mus musculus
Cmax 2.0 ng/mg Mus musculus
Cmax 49096.18 nM Mus musculus
Cmax 13.2 ng/mg Mus musculus
T1/2 1.533 hr Mus musculus
T1/2 0.6833 hr Mus musculus
T1/2 1.533 hr Mus musculus
T1/2 0.6833 hr Mus musculus
T1/2 0.9167 hr Mus musculus
T1/2 1.117 hr Mus musculus
Tmax 0.5 hr Mus musculus
Tmax 0.75 hr Mus musculus
Tmax 0.5 hr Mus musculus
Tmax 0.75 hr Mus musculus
Tmax 0.25 hr Mus musculus
Tmax 0.5 hr Mus musculus

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 = 12000.0 nM 4.92 Agonist activity at rat TRPA1 channel expressed in HEK293 cells assessed as incr... 20356305
Diacylglycerol lipase-alpha IC50 = 19400.0 nM 4.71 Inhibition of recombinant human DAGLalpha expressed in COS7 cells using [14C]-ol... 30816712
N-acylethanolamine-hydrolyzing acid amidase IC50 = 23000.0 nM 4.64 Inhibition of recombinant human NAAA expressed in HEK293 cells using [14C]-N-pal... 30816712
SARS-CoV-2 IC50 = 30700.0 nM 4.51 Antiviral activity against SARS-CoV-2 variant Delta infected in African green mo... 37402317
SARS-CoV-2 IC50 = 31700.0 nM 4.5 Antiviral activity against SARS-CoV-2 variant Omicron BA.3 infected in African g... 37402317
SARS-CoV-2 IC50 = 35100.0 nM 4.46 Antiviral activity against SARS-CoV-2 variant Omicron BA.2 infected in African g... 37402317
SARS-CoV-2 IC50 = 42700.0 nM 4.37 Antiviral activity against SARS-CoV-2 Italian strain PV10734 infected in African... 37402317
SARS-CoV-2 IC50 = 45400.0 nM 4.34 Antiviral activity against SARS-CoV-2 variant Omicron BA.1 infected in African g... 37402317
Unchecked IC50 = 47000.0 nM 4.33 Inhibition of porcine heart MDH using oxaloacetic acid as substrate preincubated... 38864383
SARS-CoV-2 IC50 = 47500.0 nM 4.32 Antiviral activity against SARS-CoV-2 variant Omicron BA.5 infected in African g... 37402317
SARS-CoV-2 IC50 = 47700.0 nM 4.32 Antiviral activity against SARS-CoV-2 variant Omicron BA.4 infected in African g... 37402317

Literature References

PubMed DOI Target Context # Activities
31686510 10.1021/acs.jnatprod.9b00600 ADMET 29
37402317 10.1021/acs.jnatprod.3c00111 SARS-CoV-2 28
18681481 10.1021/np8002673 Staphylococcus aureus 6
35007072 10.1021/acs.jnatprod.1c00946 SARS-CoV-2 5
38864383 10.1021/acs.jmedchem.4c00597 Unchecked 5
38864383 10.1021/acs.jmedchem.4c00597 No relevant target 3
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 B chain 1
32109623 10.1016/j.ejmech.2020.112163 Rattus norvegicus 1
38864383 10.1021/acs.jmedchem.4c00597 SARS-CoV-2 1
32109623 10.1016/j.ejmech.2020.112163 MDA-MB-231 1
35007072 10.1021/acs.jnatprod.1c00946 HEK-293T 1
35007072 10.1021/acs.jnatprod.1c00946 Caco-2 1
35007072 10.1021/acs.jnatprod.1c00946 Vero C1008 1
31686510 10.1021/acs.jnatprod.9b00600 Mus musculus 1

Data from ChEMBL 36 via Core Engine