Details of the Drug

General Information of Drug (ID: DMJQ4L7)

Drug Name

N-oleoylethanolamide

Synonyms

n-Oleoylethanolamine; n-oleoylethanolamine; oleoylethanolamide; N-(2-Hydroxyethyl)oleamide; 111-58-0; Oleylethanolamide; N-oleoyl ethanolamine; Oleamide MEA; Oleoyl monoethanolamide; Oleoyl Ethanolamide; N-(2-Hydroxyethyl)-9-octadecenamide; N-(Hydroxyethyl)oleamide; UNII-1HI5J9N8E6; (Z)-N-(2-hydroxyethyl)octadec-9-enamide; Oleic acid ethanolamide; N-(9Z-octadecenoyl)-ethanolamine; EINECS 203-884-8; OEA; MLS002153155; CHEMBL280065; 1HI5J9N8E6; (9Z)-N-(2-hydroxyethyl)octadec-9-enamide; Monoethanolamine oleic acid amide; CHEBI:71466; N-oleoylethanolamine; oleylethanolamide; NOE; OLEOYLETHANOLAMIDE

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

325.5

Logarithm of the Partition Coefficient (xlogp)

6.3

Rotatable Bond Count (rotbonds)

17

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

2

Chemical Identifiers

Formula: C20H39NO2
IUPAC Name: (Z)-N-(2-hydroxyethyl)octadec-9-enamide
Canonical SMILES: CCCCCCCC/C=C\\CCCCCCCC(=O)NCCO
InChI: InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
InChIKey: BOWVQLFMWHZBEF-KTKRTIGZSA-N

Cross-matching ID

PubChem CID: 5283454
ChEBI ID: CHEBI:71466
CAS Number: 111-58-0
TTD ID: D07MBC

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Cannabinoid receptor 1 (CB1)	TT6OEDT	CNR1_HUMAN	Inhibitor	[1]
G-protein coupled receptor 55 (GPR55)	TTNET8J	GPR55_HUMAN	Agonist	[2]
Glucose-dependent insulinotropic receptor (GPR119)	TT7QNVC	GP119_HUMAN	Agonist	[3]
Peroxisome proliferator-activated receptor alpha (PPARA)	TTJ584C	PPARA_HUMAN	Agonist	[4]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Regulation of Drug Effects	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Discovery agent

ICD Disease Classification

N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Cannabinoid receptor 1 (CB1)	DTT	CNR1	5.59E-02	-0.22	-0.45
Cannabinoid receptor 1 (CB1)	DTT	CNR1	7.68E-01	-0.06	-0.46

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Conformationally constrained fatty acid ethanolamides as cannabinoid and vanilloid receptor probes. J Med Chem. 2009 May 14;52(9):3001-9.
2	The orphan receptor GPR55 is a novel cannabinoid receptor. Br J Pharmacol. 2007 Dec;152(7):1092-101.
3	Screening beta-arrestin recruitment for the identification of natural ligands for orphan G-protein-coupled receptors. J Biomol Screen. 2013 Jun;18(5):599-609.
4	Oleoylethanolamide, an endogenous PPAR-alpha agonist, lowers body weight and hyperlipidemia in obese rats. Neuropharmacology. 2005 Jun;48(8):1147-53.
5	Intestinal P-glycoprotein exports endocannabinoids to prevent inflammation and maintain homeostasis. J Clin Invest. 2018 Aug 31;128(9):4044-4056. doi: 10.1172/JCI96817. Epub 2018 Aug 13.