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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 14:17:35 UTC |
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Update Date | 2018-04-16 16:59:23 UTC |
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HMDB ID | HMDB0002088 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N-Oleoylethanolamine |
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Description | N-Oleoylethanolamine (NOE or OEA) is a N-acylethanolamine. N-acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. (PMID: 12692337 , 12056855 , 12560208 , 11997249 ). N-oleoyl ethanolamine is related to the endocannabinoid anandamide. Endocannabinoids signal through cannabinoid receptors (also stimulated by the active ingredient of cannabis) but although related in structure, synthesis and degradation to anandamide, NOE cannot be considered an endocannabinoid as it does not activate the cannabinoid receptors. Most of the reported responses to NOE can be attributed to activation of peroxisome proliferator-activated receptor-alpha (PPAR-alpha). Administration of NOE inhibits body weight gain in rats. In adipocytes and hepatocytes, NOE inhibits mitogenic and metabolic signaling by the insulin receptor and produces glucose intolerance. It also inhibits gastric emptying, which might act together with the sensory neuronal signals to achieve satiety. NOE is permanently elevated in diabetic obese patients. NOE also reduces visceral and inflammatory responses through a PPAR-alpha-activation independent mechanism (PMID: 17449181 ). NOE has been shown to be an antagonist of TRVP1 (the transient receptor potential vanilloid type 1 receptor). Overall, NOE has beneficial effects on health by inducing food intake control, lipid beta-oxidation, body weight loss and analgesic effects (PMID: 18704536 ). |
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Structure | |
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Synonyms | Value | Source |
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N-(2-Hydroxyethyl)-9-octadecenamide | ChEBI | N-(2-Hydroxyethyl)oleamide | ChEBI | N-(9Z-Octadecenoyl) ethanolamine | ChEBI | N-(9Z-Octadecenoyl)-ethanolamine | ChEBI | N-(cis-9-Octadecenoyl) ethanolamine | ChEBI | N-(Hydroxyethyl)oleamide | ChEBI | N-Oleoyl ethanolamine | ChEBI | OEA | ChEBI | Oleamide mea | ChEBI | Oleoyl 1-ethanolamide | ChEBI | Oleoyl monoethanolamide | ChEBI | Oleoylethanolamide | ChEBI | N-Oleoyl ethanolamine, oleoyl monoethanolamide, oleoylethanolamide | HMDB | N-Oleoyl-2-aminoethanol | HMDB | NOE | HMDB | Oleic acid ethanolamide | HMDB | Oleic acid monoethanolamide | HMDB | N-OEA | MeSH |
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Chemical Formula | C20H39NO2 |
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Average Molecular Weight | 325.5292 |
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Monoisotopic Molecular Weight | 325.298079497 |
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IUPAC Name | (9Z)-N-(2-hydroxyethyl)octadec-9-enamide |
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Traditional Name | oleoylethanolamide |
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CAS Registry Number | 111-58-0 |
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SMILES | CCCCCCCC\C=C/CCCCCCCC(=O)NCCO |
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InChI Identifier | 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- |
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InChI Key | BOWVQLFMWHZBEF-KTKRTIGZSA-N |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as n-acylethanolamines. These are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine. |
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Kingdom | Organic compounds |
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Super Class | Organic nitrogen compounds |
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Class | Organonitrogen compounds |
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Sub Class | Amines |
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Direct Parent | N-acylethanolamines |
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Alternative Parents | |
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Substituents | - N-acylethanolamine
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Alcohol
- Organooxygen compound
- Primary alcohol
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fdn-9880000000-505c4b2acd75d00c6b4c | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9442000000-7630c4851b9379891389 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0592-2950000000-3a4675ee36a05c78c6da | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0a4i-6924100000-697643f4a75f68f27795 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01t9-5149000000-4df23e68e6a0912a6bbc | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dl-9221000000-c242848558751b665958 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01ox-9410000000-af2a86c6d06cfb4d91d9 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0029000000-6deda61377943259bcf3 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-074l-8079000000-82821facf1a599eef918 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9010000000-332b31d63933e6f4814c | View in MoNA |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Location | Not Available |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | Not Available
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Normal Concentrations |
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Blood | Detected and Quantified | 0.0036 +/- 0.00068 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 46.8 +/- 34 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB022839 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4446574 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Oleoylethanolamide |
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METLIN ID | Not Available |
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PubChem Compound | 5283454 |
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PDB ID | Not Available |
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ChEBI ID | 71466 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - 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. Epub 2003 Jan 30. [PubMed:12560208 ]
- Tripathy S, Kleppinger-Sparace K, Dixon RA, Chapman KD: N-acylethanolamine signaling in tobacco is mediated by a membrane-associated, high-affinity binding protein. Plant Physiol. 2003 Apr;131(4):1781-91. [PubMed:12692337 ]
- 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. [PubMed:12056855 ]
- Amadou A, Nawrocki A, Best-Belpomme M, Pavoine C, Pecker F: Arachidonic acid mediates dual effect of TNF-alpha on Ca2+ transients and contraction of adult rat cardiomyocytes. Am J Physiol Cell Physiol. 2002 Jun;282(6):C1339-47. [PubMed:11997249 ]
- Suardiaz M, Estivill-Torrus G, Goicoechea C, Bilbao A, Rodriguez de Fonseca F: Analgesic properties of oleoylethanolamide (OEA) in visceral and inflammatory pain. Pain. 2007 Dec 15;133(1-3):99-110. Epub 2007 Apr 20. [PubMed:17449181 ]
- Thabuis C, Tissot-Favre D, Bezelgues JB, Martin JC, Cruz-Hernandez C, Dionisi F, Destaillats F: Biological functions and metabolism of oleoylethanolamide. Lipids. 2008 Oct;43(10):887-94. doi: 10.1007/s11745-008-3217-y. Epub 2008 Aug 13. [PubMed:18704536 ]
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