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Compound Detail

CHEMBL15848

ANANDAMIDE
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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO

Basic Information

ChEMBL ID CHEMBL15848
Name ANANDAMIDE
Phase Preclinical
Structure Type MOL
InChI Key LGEQQWMQCRIYKG-DOFZRALJSA-N
21
Targets
83
Activities
3
Assay Types
20
PK Parameters
20
Publications
0
Known Names

Molecular Properties

347.5
MW (Da)
5.24
ALogP
2
HBA
2
HBD
49.3
PSA (Ų)
0.30
QED
1
Ro5 Violations
16
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C22H37NO2
MW 347.54
Aromatic Rings 0
Heavy Atoms 25
NP-Likeness 0.58

Activity Summary

Ki 58 meas. best 7.96
IC50 16 meas. best 7.41
EC50 9 meas. best 7.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cannabinoid receptor 1
CHEMBL218
Ki 7.96 7.0181 11.0 21
Transient receptor potential cation channel subfamily V member 1
CHEMBL4794
EC50 7.8 6.7525 15.8 4
Cannabinoid receptor 1
CHEMBL3571
Ki 7.66 6.7882 22.0 17
Cannabinoid receptor
CHEMBL2111385
Ki 7.6 7.0867 25.0 3
Cannabinoid receptor 1
CHEMBL3037
IC50 7.41 6.165 39.0 2
Cannabinoid receptor 1
CHEMBL3571
IC50 7.4 7.4 40.0 1
Cannabinoid receptor
CHEMBL2111415
Ki 7.28 7.28 52.0 1
Mus musculus
CHEMBL375
EC50 7.28 7.28 52.7 1
Mus musculus
CHEMBL375
IC50 7.28 7.28 52.0 1
Cannabinoid receptor 1
CHEMBL3571
EC50 7.16 5.5867 69.0 3
Cannabinoid receptor 1
CHEMBL3037
Ki 7.05 6.16 89.0 2
Cannabinoid receptor 2
CHEMBL253
Ki 6.8 6.68 160.0 8
Transient receptor potential cation channel subfamily V member 1
CHEMBL5102
Ki 6.77 6.77 169.0 1
Cannabinoid receptor 2
CHEMBL2470
Ki 6.44 6.44 360.0 1
Cannabinoid receptor 1
CHEMBL3037
EC50 6.44 6.44 360.0 1
Unchecked
CHEMBL612545
Ki 6.43 6.43 370.0 1
Transient receptor potential cation channel subfamily V member 2
CHEMBL2863
IC50 6.02 5.545 960.0 2
Potassium channel subfamily K member 2
CHEMBL1075183
IC50 6.0 6.0 1000.0 1
Cannabinoid receptor 2
CHEMBL5373
Ki 5.71 5.71 1926.0 2
Fatty-acid amide hydrolase 1
CHEMBL3229
Ki 5.52 5.52 3000.0 1
Potassium channel subfamily K member 3
CHEMBL2321613
IC50 5.52 5.52 3000.0 1
Fatty-acid amide hydrolase 1
CHEMBL2243
IC50 5.47 5.43 3400.0 2
Fatty-acid amide hydrolase 1
CHEMBL3229
IC50 4.93 4.93 11749.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 4.85 4.775 14000.0 2
RBL-2H3
CHEMBL614632
IC50 4.84 4.84 14500.0 1
Acanthamoeba castellanii
CHEMBL614744
IC50 4.77 4.77 17000.0 1
Rattus norvegicus
CHEMBL376
IC50 4.72 4.72 19000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 311.6 ng.hr/g Rattus norvegicus
AUC 9.5 ng.hr.mL-1 Rattus norvegicus
AUC 232.9 ng.hr/g Rattus norvegicus
AUC 7.9 ng.hr.mL-1 Rattus norvegicus
AUC 64.3 ng.hr/g Rattus norvegicus
AUC 3.4 ng.hr.mL-1 Rattus norvegicus
Cmax 19.2 ng/g Rattus norvegicus
Cmax 1.439 nM Rattus norvegicus
Cmax 19.1 ng/g Rattus norvegicus
Cmax 1.151 nM Rattus norvegicus
Cmax 6.8 ng/g Rattus norvegicus
Cmax 0.5755 nM Rattus norvegicus
T1/2 0.2017 hr Rattus norvegicus
T1/2 0.22 hr Homo sapiens
Tmax 4.0 hr Rattus norvegicus
Tmax 12.0 hr Rattus norvegicus
Tmax 4.0 hr Rattus norvegicus
Tmax 8.0 hr Rattus norvegicus
Tmax 4.0 hr Rattus norvegicus
Tmax 8.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cannabinoid receptor 1 Ki = 11.0 nM 7.96 Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in HE... 19361197
Transient receptor potential cation channel subfamily V member 1 EC50 = 15.8 nM 7.8 Agonist activity at TRPV1 receptor (unknown origin) 23384387
Cannabinoid receptor 1 Ki = 22.0 nM 7.66 Displacement of [3H]CP-55940 binding to Cannabinoid receptor 1 in rat brain memb... 9784095
Cannabinoid receptor Ki = 25.0 nM 7.6 Binding affinity towards cannabinoid receptor using [3H]CP-55940 as radioligand ... 9357529
Cannabinoid receptor 1 Ki = 39.2 nM 7.41 Compound was evaluated for its binding affinity towards Cannabinoid receptor 1 [... 12166938
Cannabinoid receptor 1 Ki = 39.2 nM 7.41 In vitro binding affinity was determined against rat brain Cannabinoid receptor ... 9057852
Cannabinoid receptor 1 IC50 = 39.0 nM 7.41 Binding affinity towards Cannabinoid receptor 1 was determined using [3H]-CP- ca... 12951114
Cannabinoid receptor 1 IC50 = 40.0 nM 7.4 Binding affinity towards Cannabinoid receptor 1 was determined using [3H]-CP- ca... 12951114
Cannabinoid receptor 1 Ki = 50.0 nM 7.3 Binding affinity to CB1R (unknown origin) 27766867
Cannabinoid receptor 1 Ki = 50.0 nM 7.3 Binding affinity for human cannabinoid receptor 1 16078824
Mus musculus EC50 = 52.7 nM 7.28 Effective concentration that causes twitch inhibition in a mouse vas deferens as... 9357529
Cannabinoid receptor Ki = 52.0 nM 7.28 Ability to displace [3H]HU-243 binding to cannabinoid receptor in synaptosomal m... 8411021
Mus musculus IC50 = 52.0 nM 7.28 Tested for potency towards inhibition of the twitch response in mouse vas defere... 8021930
Cannabinoid receptor 1 Ki = 61.0 nM 7.21 Binding affinity towards cannabinoid receptor 1 from rat forebrain membranes in ... 9876105
Cannabinoid receptor 1 Ki = 70.0 nM 7.16 Displacement of [3H]CP55940 from human CB1 receptor expressed in human HEK293 ce... 22044209
Cannabinoid receptor 1 EC50 = 69.0 nM 7.16 Agonist activity at rat CB1 receptor expressed in HEK293 cells assessed as inhib... 30196704
Cannabinoid receptor 1 Ki = 70.0 nM 7.16 Displacement of [3H]CP-55-940 from human recombinant CB1 receptor expressed in C... 19161308
Cannabinoid receptor 1 Ki = 70.0 nM 7.16 Binding affinity to human recombinant CB1 receptor expressed in COS cells 16570929
Cannabinoid receptor 1 Ki = 70.0 nM 7.16 Displacement of [3H]CP-55-940 from human recombinant CB1 receptor in COS cells 16682198
Cannabinoid receptor 1 Ki = 72.0 nM 7.14 Displacement of [3H]-CP55940 from human recombinant CB1 receptor expressed in HE... 32340793

Literature References

PubMed DOI Target Context # Activities
10072686 10.1021/jm980461j Fatty-acid amide hydrolase 1 18
20479202 10.1128/aac.01825-09 NON-PROTEIN TARGET 12
24440478 10.1016/j.bmc.2013.12.023 Brain 9
24440478 10.1016/j.bmc.2013.12.023 Plasma 9
8021930 10.1021/jm00038a020 Mus musculus 9
20479202 10.1128/aac.01825-09 Acanthamoeba castellanii 6
9357529 10.1021/jm9702950 Mus musculus 6
14613317 10.1021/jm0302647 Cannabinoid receptor 1 6
21899370 10.1021/jm200723m Fatty-acid amide hydrolase 1 6
11229744 10.1016/s0960-894x(00)00689-2 Rattus norvegicus 4
30196704 10.1021/acs.jmedchem.8b00611 Cannabinoid receptor 1 4
9357528 10.1021/jm970212f Mus musculus 4
10354405 10.1021/jm980711w Mus musculus 4
19361197 10.1021/jm900130m Cannabinoid receptor 1 3
12951114 10.1016/s0960-894x(03)00721-2 Cannabinoid receptor 1 3
8558515 10.1021/jm9505167 Mus musculus 2
16078824 10.1021/jm058183t Cannabinoid receptor 1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
16420041 10.1021/jm0505157 Cannabinoid receptor 1 2
10328303 10.1016/s0960-894x(99)00148-1 Rattus norvegicus 2

Data from ChEMBL 36 via Core Engine