NAV

Oleic monoethanolamide

Identification

Generic Name
Oleic monoethanolamide
DrugBank Accession Number
DB16495
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 325.537
Monoisotopic: 325.2980795
Chemical Formula
C20H39NO2
Synonyms
  • N-(2-Hydroxyethyl)oleamide
  • N-OEA
  • N-oleoyl ethanolamine
  • N-oleoylethanolamine
  • OEA
  • Oleamide MEA
  • Oleoyl Ethanolamide
  • Oleoyl monoethanolamide
  • Oleoylethanolamide
  • Oleylethanolamide
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action

Oleoylethanolamide (OEA) is a major N-acylethanolamine and an endogenous ethanolamide fatty acid. Although it is an endocannabinoids-like compound, it does not bind to cannabinoid receptors. Instead, this lipid sensor is an agonist at peroxisome proliferator-activated receptor-α (PPAR-α) agonist while also being an inhibitor of ceramidase and thereby the sphingolipid signaling pathway.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
1HI5J9N8E6
CAS number
111-58-0
InChI Key
BOWVQLFMWHZBEF-KTKRTIGZSA-N
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-
IUPAC Name
(9Z)-N-(2-hydroxyethyl)octadec-9-enamide
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)NCCO

References

General References
  1. Payahoo L, Khajebishak Y, Asghari Jafarabadi M, Ostadrahimi A: Oleoylethanolamide Supplementation Reduces Inflammation and Oxidative Stress in Obese People: A Clinical Trial. Adv Pharm Bull. 2018 Aug;8(3):479-487. doi: 10.15171/apb.2018.056. Epub 2018 Aug 29. [Article]
  2. Di Paola M, Bonechi E, Provensi G, Costa A, Clarke G, Ballerini C, De Filippo C, Passani MB: Oleoylethanolamide treatment affects gut microbiota composition and the expression of intestinal cytokines in Peyer's patches of mice. Sci Rep. 2018 Oct 5;8(1):14881. doi: 10.1038/s41598-018-32925-x. [Article]
  3. Tsuboi K, Uyama T, Okamoto Y, Ueda N: Endocannabinoids and related N-acylethanolamines: biological activities and metabolism. Inflamm Regen. 2018 Oct 1;38:28. doi: 10.1186/s41232-018-0086-5. eCollection 2018. [Article]
  4. Hofmann U, Domeier E, Frantz S, Laser M, Weckler B, Kuhlencordt P, Heuer S, Keweloh B, Ertl G, Bonz AW: Increased myocardial oxygen consumption by TNF-alpha is mediated by a sphingosine signaling pathway. Am J Physiol Heart Circ Physiol. 2003 Jun;284(6):H2100-5. doi: 10.1152/ajpheart.00888.2002. Epub 2003 Jan 30. [Article]
  5. Lecour S, Smith RM, Woodward B, Opie LH, Rochette L, Sack MN: Identification of a novel role for sphingolipid signaling in TNF alpha and ischemic preconditioning mediated cardioprotection. J Mol Cell Cardiol. 2002 May;34(5):509-18. doi: 10.1006/jmcc.2002.1533. [Article]
Human Metabolome Database
HMDB0002088
ChemSpider
4446574
BindingDB
29080
ChEBI
71466
ChEMBL
CHEMBL280065
ZINC
ZINC000008034993
PDBe Ligand
5YM
PDB Entries
7v7w

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP5.51Chemaxon
pKa (Strongest Acidic)15.47Chemaxon
pKa (Strongest Basic)-1.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area49.33 Å2Chemaxon
Rotatable Bond Count17Chemaxon
Refractivity100.41 m3·mol-1Chemaxon
Polarizability42.64 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004l-9124000000-7269ed0ee9c5fd68218e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fr-1039000000-751ab1ab7b31aef416fd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-066r-5095000000-1bba972878517be047db
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9111000000-16852deb1006c812e34a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-066u-9160000000-e835d891bbd0a487cf44
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-9100000000-574f0be64e14203441d3
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-222.1049958
predicted
DarkChem Lite v0.1.0
[M-H]-223.3748958
predicted
DarkChem Lite v0.1.0
[M-H]-190.67078
predicted
DeepCCS 1.0 (2019)
[M+H]+222.9633958
predicted
DarkChem Lite v0.1.0
[M+H]+222.5571958
predicted
DarkChem Lite v0.1.0
[M+H]+193.18687
predicted
DeepCCS 1.0 (2019)
[M+Na]+220.9338958
predicted
DarkChem Lite v0.1.0
[M+Na]+222.3840958
predicted
DarkChem Lite v0.1.0
[M+Na]+199.82352
predicted
DeepCCS 1.0 (2019)

Drug created at January 21, 2021 02:01 / Updated at January 24, 2021 06:04