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Compound Detail

CHEMBL120526

METHANANDAMIDE
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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N[C@H](C)CO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL120526
Name METHANANDAMIDE
Phase Preclinical
Structure Type MOL
InChI Key SQKRUBZPTNJQEM-FQPARAGTSA-N
7
Targets
22
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

361.6
MW (Da)
5.63
ALogP
2
HBA
2
HBD
49.3
PSA (Ų)
0.28
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 C23H39NO2
MW 361.57
Aromatic Rings 0
Heavy Atoms 26
NP-Likeness 0.58

Activity Summary

Ki 17 meas. best 7.75
EC50 3 meas. best 8.0
IC50 2 meas. best 7.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mus musculus
CHEMBL375
 EC50 8.0 8.0 10.1 1
Mus musculus
CHEMBL375
 IC50 7.92 7.92 12.0 1
Cannabinoid receptor 1
CHEMBL3571
 Ki 7.75 7.59 17.9 8
Cannabinoid receptor
CHEMBL2111385
 Ki 7.7 7.285 20.0 4
Potassium channel subfamily K member 3
CHEMBL2321613
 IC50 7.0 7.0 100.0 1
Cannabinoid receptor 2
CHEMBL253
 Ki 6.66 6.66 220.0 1
Rattus norvegicus
CHEMBL376
 EC50 6.48 6.48 330.0 1
Cannabinoid receptor 2
CHEMBL5373
 Ki 6.09 6.075 815.0 4

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mus musculus EC50 = 10.1 nM 8.0 Effective concentration that causes twitch inhibition in a mouse vas deferens as... 9357529
Mus musculus IC50 = 12.0 nM 7.92 Tested for potency towards inhibition of the twitch response in mouse vas defere... 8021930
Cannabinoid receptor 1 Ki = 17.9 nM 7.75 Binding affinity towards cannabinoid receptor 1 from rat forebrain membranes in ... 9876105
Cannabinoid receptor 1 Ki = 17.9 nM 7.75 Displacement of [3H]CP-55940 from cannabinoid CB1 receptor in rat brain membrane... 18723350
Cannabinoid receptor Ki = 20.0 nM 7.7 Binding affinity for the cannabinoid receptor in the presence of phenylmethanesu... 8021930
Cannabinoid receptor 1 Ki = 20.0 nM 7.7 Tested for binding affinity to Cannabinoid receptor 1 10072686
Cannabinoid receptor 1 Ki = 20.0 nM 7.7 Displacement of [3H]CP-55940 from Cannabinoid receptor 1 of rat forebrain membra... 8893848
Cannabinoid receptor 1 Ki = 20.0 nM 7.7 Displacement of [3H]-CP55940 from CB1 receptor of rat cerebellar membranes by li... 23865723
Cannabinoid receptor Ki = 22.0 nM 7.66 Binding affinity towards cannabinoid receptor using [3H]CP-55940 as radioligand ... 9357529
Cannabinoid receptor 1 Ki = 28.3 nM 7.55 Binding affinity towards cannabinoid receptor 1 from rat forebrain membranes in ... 9876105
Cannabinoid receptor Ki = 28.0 nM 7.55 Binding affinity for the cannabinoid receptor in the absence of phenylmethanesul... 8021930
Cannabinoid receptor 1 Ki = 37.0 nM 7.43 Displacement of [3H]CP-55,940 from CB1 receptor in rat brain membranes in presen... 30196704
Cannabinoid receptor 1 Ki = 72.0 nM 7.14 Displacement of [3H]CP-55,940 from CB1 receptor in rat brain membranes in absenc... 30196704
Potassium channel subfamily K member 3 IC50 = 100.0 nM 7.0 Inhibition of human TASK1 expressed in African green monkey COS cells by whole c... 31260312
Cannabinoid receptor 2 Ki = 220.0 nM 6.66 Displacement of [3H]CP-55,940 from human CB2 receptor expressed in HEK293 cell m... 30196704
Rattus norvegicus EC50 = 330.0 nM 6.48 Effective concentration required for stimulation of [35S]GTP-gamma-S, binding in... 9876105
Cannabinoid receptor Ki = 585.0 nM 6.23 Binding affinity towards cannabinoid receptor using [3H]SR-141,716A as radioliga... 9357529
Cannabinoid receptor 2 Ki = 815.0 nM 6.09 Compound was evaluated for its binding affinity for mouse spleen Cannabinoid rec... 8893848
Cannabinoid receptor 2 Ki = 815.0 nM 6.09 Binding affinity to mouse spleen CB2 receptor 23865723
Cannabinoid receptor 2 Ki = 868.0 nM 6.06 Binding affinity towards Cannabinoid receptor 2 from mouse spleen membranes usin... 9876105

Literature References

PubMed DOI Target Context # Activities
8021930 10.1021/jm00038a020 Mus musculus 9
19161308 10.1021/jm8011382 Matrix metalloproteinase-9 6
19161308 10.1021/jm8011382 72 kDa type IV collagenase 6
10072686 10.1021/jm980461j Fatty-acid amide hydrolase 1 4
30196704 10.1021/acs.jmedchem.8b00611 Mus musculus 4
9876105 10.1021/jm970257g Rattus norvegicus 3
9357529 10.1021/jm9702950 Cannabinoid receptor 2
30196704 10.1021/acs.jmedchem.8b00611 Cannabinoid receptor 2 2
30196704 10.1021/acs.jmedchem.8b00611 Cannabinoid receptor 1 2
9357529 10.1021/jm9702950 Mus musculus 2
9876105 10.1021/jm970257g Cannabinoid receptor 1 2
8021930 10.1021/jm00038a020 Cannabinoid receptor 2
8893848 10.1021/jm960152y Cannabinoid receptor 2 1
8893848 10.1021/jm960152y Cannabinoid receptor 1 1
10072686 10.1021/jm980461j Unchecked 1
18723350 10.1016/j.bmcl.2008.07.110 Cannabinoid receptor 1 1
18723350 10.1016/j.bmcl.2008.07.110 Cannabinoid receptor 2 1
23865723 10.1021/jm4005626 Cannabinoid receptor 1 1
31260312 10.1021/acs.jmedchem.9b00248 Potassium channel subfamily K member 3 1
10072686 10.1021/jm980461j Cannabinoid receptor 1 1

Data from ChEMBL 36 via Core Engine