Compound Detail

CHEMBL280065

OLEOYLETHANOLAMIDE

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CCCCCCCC/C=C\CCCCCCCC(=O)NCCO

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL280065
Name	OLEOYLETHANOLAMIDE
Phase	Preclinical
Structure Type	MOL
InChI Key	BOWVQLFMWHZBEF-KTKRTIGZSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

325.5

MW (Da)

5.13

ALogP

HBA

HBD

49.3

PSA (Å²)

0.29

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C20H39NO2
MW	325.54
Aromatic Rings	0
Heavy Atoms	23
NP-Likeness	0.38

Activity Summary

EC50 20 meas. best 7.4

IC50 16 meas. best 5.75

Ki 6 meas. best 5.96

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Transient receptor potential cation channel subfamily V member 1 CHEMBL4794	EC50	7.4	6.2967	40.0	3
Peroxisome proliferator-activated receptor alpha CHEMBL239	EC50	6.96	6.85	110.0	5
Glucose-dependent insulinotropic receptor CHEMBL5652	EC50	6.03	5.6671	930.0	7
Cannabinoid receptor 1 CHEMBL218	Ki	5.96	5.96	1100.0	2
Peroxisome proliferator-activated receptor delta CHEMBL3979	EC50	5.96	5.96	1100.0	1
Transient receptor potential cation channel subfamily V member 2 CHEMBL2863	IC50	5.75	5.51	1800.0	2
Plasmodium falciparum CHEMBL364	IC50	5.7	5.3429	1995.3	7
Glucose-dependent insulinotropic receptor CHEMBL5263	EC50	5.54	5.54	2900.0	1
NAD-dependent protein deacylase sirtuin-6 CHEMBL2163182	EC50	5.51	5.51	3100.0	3
Cannabinoid receptor 1 CHEMBL3571	Ki	4.7	4.53	20000.0	2
RBL-2H3 CHEMBL614632	IC50	4.7	4.7	20000.0	1
Rattus norvegicus CHEMBL376	IC50	4.64	4.64	23000.0	1
Unchecked CHEMBL612545	IC50	4.62	4.36	24000.0	4
Cannabinoid receptor 2 CHEMBL5373	Ki	4.51	4.51	31000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Transient receptor potential cation channel subfamily V member 1	EC50	=	40.0	nM	7.4	Agonist activity at TRPV1 receptor (unknown origin)	23384387
Peroxisome proliferator-activated receptor alpha	EC50	=	110.0	nM	6.96	Activation of human PPARalpha by GST pull down assay	17228882
Peroxisome proliferator-activated receptor alpha	EC50	=	120.0	nM	6.92	Transactivation of human Gal4 fused PPARalpha LBD transfected in human HeLa cell...	27622746
Peroxisome proliferator-activated receptor alpha	EC50	=	152.0	nM	6.82	Agonist activity at human PPARalpha expressed in MCF7 cells co-transfected CPTI ...	24936232
Peroxisome proliferator-activated receptor alpha	EC50	=	152.0	nM	6.82	Agonist activity at human PPARalpha transfected in human MCF7 cells after 16 hrs...	26226490
Peroxisome proliferator-activated receptor alpha	EC50	=	185.0	nM	6.73	Agonist activity at human PPARalpha expressed in MCF7 cells co-transfected CPTI ...	24936232
Transient receptor potential cation channel subfamily V member 1	EC50	=	890.0	nM	6.05	Agonist activity on human recombinant TRPV1-mediated enhancement of intracellula...	16570929
Glucose-dependent insulinotropic receptor	EC50	=	930.0	nM	6.03	Agonist activity at GPR119 (unknown origin) assessed as increase in cAMP level b...	31898998
Peroxisome proliferator-activated receptor delta	EC50	=	1100.0	nM	5.96	Transactivation of human Gal4 fused PPARdelta LBD transfected in human HeLa cell...	27622746
Cannabinoid receptor 1	Ki	=	1100.0	nM	5.96	Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in HE...	19361197
Cannabinoid receptor 1	Ki	=	1100.0	nM	5.96	Binding affinity to human recombinant CB1 receptor expressed in COS cells	16570929
Transient receptor potential cation channel subfamily V member 2	IC50	=	1800.0	nM	5.75	Antagonist activity at recombinant rat TRPV2 expressed in HEK293 cells assessed ...	30176215
Plasmodium falciparum	IC50	=	1995.26	nM	5.7	Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr...	19734910
Glucose-dependent insulinotropic receptor	EC50	=	2200.0	nM	5.66	Agonist activity at human GPR119 expressed in HEK293 cells assessed as stimulati...	27825553
Glucose-dependent insulinotropic receptor	EC50	=	2200.0	nM	5.66	Agonist activity at human GPR119 expressed in HEK293 cells assessed as cAMP accu...	23357035
Glucose-dependent insulinotropic receptor	EC50	=	2200.0	nM	5.66	Agonist activity at human GPR119 transfected in HEK293 cells assessed as concent...	23374864
Glucose-dependent insulinotropic receptor	EC50	=	2200.0	nM	5.66	Agonist activity at human GPR119 expressed in HEK293 cells assessed as increase ...	28408218
Glucose-dependent insulinotropic receptor	EC50	=	2900.0	nM	5.54	Agonist activity at mouse GPR119 receptor cotransformed in Saccharomyces cerevis...	26512410
NAD-dependent protein deacylase sirtuin-6	EC50	=	3100.0	nM	5.51	Activation of his6-tagged SIRT6 (unknown origin) using H3K9Ac peptide substrate ...	36508969
NAD-dependent protein deacylase sirtuin-6	EC50	=	3100.0	nM	5.51	Activation of recombinant His-tagged SIRT6 (unknown origin) deacetylase activity...	34213345

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL5303304	U2OS	10
23384387	10.1021/jm300484d	Mus musculus	9
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
-	10.6019/CHEMBL5303304	Fibroblast	6
20085856	10.1016/j.bmc.2009.12.071	Unchecked	6
-	10.6019/CHEMBL5303304	HEK-293T	5
25510639	10.1016/j.bmc.2014.11.019	NON-PROTEIN TARGET	4
34213345	10.1021/acs.jmedchem.1c00601	NAD-dependent protein deacylase sirtuin-6	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
20667727	10.1016/j.bmcl.2010.06.149	Mycobacterium tuberculosis	3
16570929	10.1021/jm051240y	Transient receptor potential cation channel subfamily V member 1	2
36508969	10.1016/j.ejmech.2022.114998	NAD-dependent protein deacylase sirtuin-6	2
25510639	10.1016/j.bmc.2014.11.019	MCF7	2
25510639	10.1016/j.bmc.2014.11.019	U-251	2
17228882	10.1021/jm0601102	Peroxisome proliferator-activated receptor alpha	2
25510639	10.1016/j.bmc.2014.11.019	NCI/ADR-RES	2
10328303	10.1016/s0960-894x(99)00148-1	Rattus norvegicus	2
25510639	10.1016/j.bmc.2014.11.019	HaCaT	2
10072686	10.1021/jm980461j	Fatty-acid amide hydrolase 1	2
25510639	10.1016/j.bmc.2014.11.019	NCI-H460	2

Data from ChEMBL 36 via Core Engine