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Compound Detail

CHEMBL122972

2-ARACHIDONOYLGLYCEROL
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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO)CO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL122972
Name 2-ARACHIDONOYLGLYCEROL
Phase Preclinical
Structure Type MOL
InChI Key RCRCTBLIHCHWDZ-DOFZRALJSA-N
7
Targets
19
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

378.6
MW (Da)
5.03
ALogP
4
HBA
2
HBD
66.8
PSA (Ų)
0.21
QED
1
Ro5 Violations
17
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C23H38O4
MW 378.55
Aromatic Rings 0
Heavy Atoms 27
NP-Likeness 1.23

Activity Summary

Ki 14 meas. best 7.0
EC50 5 meas. best 7.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cannabinoid receptor 2
CHEMBL253
 EC50 7.77 7.77 17.0 1
Cannabinoid receptor 2
CHEMBL5373
 EC50 7.75 7.75 18.0 1
Cannabinoid receptor 1
CHEMBL218
 EC50 7.64 7.64 23.0 1
Cannabinoid receptor 1
CHEMBL3571
 EC50 7.6 6.8 25.0 2
Cannabinoid receptor 2
CHEMBL2470
 Ki 7.0 7.0 100.0 1
Cannabinoid receptor 1
CHEMBL3571
 Ki 7.0 6.5533 100.0 3
Cannabinoid receptor 1
CHEMBL218
 Ki 6.33 6.245 470.0 4
Cannabinoid receptor 2
CHEMBL253
 Ki 5.89 5.86 1300.0 4
Unchecked
CHEMBL612545
 Ki 5.52 5.52 3000.0 1
Fatty-acid amide hydrolase 1
CHEMBL2243
 Ki 5.3 5.3 5000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cannabinoid receptor 2 EC50 = 17.0 nM 7.77 Agonist activity at CB2 receptor expressed in HL60 cells assessed as increase in... 17110113
Cannabinoid receptor 2 EC50 = 18.0 nM 7.75 Agonist activity at mouse CB2 receptor stably expressed in HEK293 cells assessed... 38894922
Cannabinoid receptor 1 EC50 = 23.0 nM 7.64 Agonist activity at CB1 receptor expressed in NG108-15 cells assessed as increas... 17110113
Cannabinoid receptor 1 EC50 = 25.0 nM 7.6 Agonist activity at rat CB1 receptor stably expressed in HEK293 cells assessed a... 38894922
Cannabinoid receptor 1 Ki = 100.0 nM 7.0 Displacement of [3H]CP-55940 from rat forebrain membrane which expresses Cannabi... 12166944
Cannabinoid receptor 2 Ki = 100.0 nM 7.0 Displacement of [3H]CP-55940 from rat forebrain membrane which expresses Cannabi... 12166944
Cannabinoid receptor 1 Ki = 472.0 nM 6.33 Displacement of [3H]CP55940 from CB1 receptor in Wistar rat brain incubated for ... 26890113
Cannabinoid receptor 1 Ki = 472.0 nM 6.33 Binding affinity to CB1 receptor (unknown origin) 27624523
Cannabinoid receptor 1 Ki = 472.0 nM 6.33 Binding affinity to rat CB1 receptor 23865723
Cannabinoid receptor 1 Ki = 470.0 nM 6.33 Displacement of [3H]CP55940 from human CB1 receptor expressed in human HEK293 ce... 22044209
Cannabinoid receptor 1 Ki = 480.0 nM 6.32 Displacement of [3H]-CP55940 from human CB1 receptor expressed in HEK-293-EBNA c... 21675776
Cannabinoid receptor 1 EC50 = 1000.0 nM 6.0 Potency at CB1 receptor in rat brain by [35S]GTP-gamma-S binding assay 16466915
Cannabinoid receptor 1 Ki = 1000.0 nM 6.0 Binding affinity to CB1R (unknown origin) 27766867
Cannabinoid receptor 2 Ki = 1300.0 nM 5.89 Displacement of [3H]-CP55940 from human CB2 receptor expressed in HEK-293-EBNA c... 21675776
Cannabinoid receptor 2 Ki = 1400.0 nM 5.85 Displacement of [3H]CP55940 from human CB2 receptor expressed in human HEK293 ce... 22044209
Cannabinoid receptor 2 Ki = 1400.0 nM 5.85 Binding affinity to human CB2 receptor 23865723
Cannabinoid receptor 2 Ki = 1400.0 nM 5.85 Binding affinity to CB2 receptor (unknown origin) 27624523
Unchecked Ki = 3000.0 nM 5.52 Inhibition of N-arachidonoylethanolamine transporter (AEA) activity in human lym... 12166944
Fatty-acid amide hydrolase 1 Ki = 5000.0 nM 5.3 Inhibition of Fatty-acid amide hydrolase (FAAH) activity in human lymphoma U937 ... 12166944

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5058564 HEK-293T 7
- 10.6019/CHEMBL5058564 U2OS 4
20479202 10.1128/aac.01825-09 NON-PROTEIN TARGET 2
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 2
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 2
- 10.6019/CHEMBL5209801 Apelin receptor 2
- 10.6019/CHEMBL5209801 G-protein coupled receptor 35 2
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 2
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 2
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 2
10072686 10.1021/jm980461j Fatty-acid amide hydrolase 1 2
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 2
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 2
17110113 10.1016/j.bmc.2006.10.049 Cannabinoid receptor 2 2
17110113 10.1016/j.bmc.2006.10.049 Cannabinoid receptor 1 2
16466915 10.1016/j.bmcl.2006.01.101 Cannabinoid receptor 1 2
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 2
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 2
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 2
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 2

Data from ChEMBL 36 via Core Engine