Oleoylethanolamide (BioDeep_00000018228)

 

Secondary id: BioDeep_00000015031, BioDeep_00000569143

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


N-Oleoyl ethanolamine, oleoyl monoethanolamide, oleoylethanolamide

化学式: C20H39NO2 (325.2980634)
中文名称: 油酰单乙醇胺, 油酰乙醇酰胺
谱图信息: 最多检出来源 Homo sapiens(feces) 0.18%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Oleoylethanolamide. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/oleoylethanolamide (retrieved 2024-10-18) (BioDeep RN: BioDeep_00000018228). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

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

描述信息

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). [HMDB]
Oleoylethanolamide (OEA or NOE) is an 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 have been attributed to a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. Oleoylethanolamide is an inhibitor of the sphingolipid signalling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). Oleoylethanolamide blocks the effects of TNF and arachidonic acid on intracellular Ca concentration (PMID: 12692337, 12056855, 12560208, 11997249). Oleoylethanolamide 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, OEA cannot be considered an endocannabinoid as it does not activate the cannabinoid receptors. Most of the reported responses to OEA can be attributed to the activation of peroxisome proliferator-activated receptor-alpha (PPAR-alpha). Administration of OEA inhibits body weight gain in rats. In adipocytes and hepatocytes, OEA inhibits mitogenic and metabolic signalling 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. OEA is permanently elevated in diabetic obese patients. OEA also reduces visceral and inflammatory responses through a PPAR-alpha-activation independent mechanism (PMID: 17449181). OEA is an antagonist of TRVP1 (the transient receptor potential vanilloid type 1 receptor). Overall, OEA has beneficial effects on health by inducing food intake control, lipid beta-oxidation, body weight loss and analgesic effects (PMID: 18704536).
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D063385 - Cannabinoid Receptor Modulators
D018377 - Neurotransmitter Agents > D063385 - Cannabinoid Receptor Modulators > D063386 - Cannabinoid Receptor Agonists
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Oleoylethanolamide is a high affinity endogenous PPAR-α agonist, which plays an important role in the treatment of obesity and arteriosclerosis.
Oleoylethanolamide is a high affinity endogenous PPAR-α agonist, which plays an important role in the treatment of obesity and arteriosclerosis.

同义名列表

27 个代谢物同义名

N-Oleoyl ethanolamine, oleoyl monoethanolamide, oleoylethanolamide; (9Z)-N-(2-hydroxyethyl)octadec-9-enamide; (9Z)-N-(2-Hydroxyethyl)-9-octadecenamide; N-(2-Hydroxyethyl)-9-Z-octadecenamide; N-(cis-9-octadecenoyl) ethanolamine; N-(2-hydroxyethyl)octadec-9-enamide; N-(2-Hydroxyethyl)-9-octadecenamide; N-(9Z-Octadecenoyl) ethanolamine; N-(9Z-octadecenoyl)-ethanolamine; Oleic acid monoethanolamide; N-(2-Hydroxyethyl)oleamide; N-(Hydroxyethyl)oleamide; Oleoyl monoethanolamide; Oleic acid ethanolamide; N-Oleoyl-2-aminoethanol; Oleoyl 1-ethanolamide; N-oleoyl ethanolamine; N-Oleoylethanolamine; N-Oleoylethanolamide; Oleoyl ethanolamide; Oleoylethanolamine; Oleoylethanolamide; Oleamide mea; N-OEA; NOE; OEA; Oleoylethanolamide



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

7 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

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