N-acylethanolamine metabolic process
Definition
Target type: biologicalprocess
The chemical reactions and pathways involving N-acylethanolamines. An N-acylethanolamine is an ethanolamine substituted at nitrogen by an acyl group. [CHEBI:52640, GOC:elh, PMID:14634025, PMID:15878693]
N-acylethanolamines (NAEs) are a class of lipid signaling molecules that play crucial roles in various physiological processes, including inflammation, pain perception, appetite regulation, and neurotransmission. The N-acylethanolamine metabolic process encompasses the biosynthesis, degradation, and signaling of NAEs.
**Biosynthesis:**
NAEs are synthesized from membrane phospholipids via the enzymatic activity of N-acyl-phosphatidylethanolamine-specific phospholipase D (NAPE-PLD). This enzyme hydrolyzes N-acyl-phosphatidylethanolamine (NAPE), a precursor molecule, to generate NAE and phosphatidic acid. The specific type of NAE produced depends on the fatty acyl chain attached to the NAPE molecule.
**Degradation:**
NAEs are primarily degraded by the enzyme fatty acid amide hydrolase (FAAH). FAAH hydrolyzes the amide bond between the fatty acid and ethanolamine, producing a free fatty acid and ethanolamine. This hydrolysis reaction terminates the signaling activity of NAEs.
**Signaling:**
NAEs exert their biological effects by interacting with specific receptors on target cells. The most well-characterized NAE receptor is the peroxisome proliferator-activated receptor alpha (PPARα), which is involved in lipid metabolism and inflammation. Other NAE receptors include the vanilloid receptor 1 (TRPV1), which mediates pain sensation, and the G protein-coupled receptor 119 (GPR119), which regulates insulin secretion.
**Regulation:**
The N-acylethanolamine metabolic process is tightly regulated by a variety of factors, including enzymatic activity, substrate availability, and receptor expression. For example, stress, inflammation, and diet can influence the levels of NAEs and their enzymes.
**Biological Significance:**
The N-acylethanolamine metabolic process is essential for maintaining normal physiological function. Dysregulation of this process has been implicated in a wide range of diseases, including obesity, diabetes, cancer, and neurodegenerative disorders.
**Examples of NAEs:**
Some common examples of NAEs include:
* Anandamide (AEA): An endocannabinoid that plays a role in pain perception, appetite, and memory.
* Oleoylethanolamide (OEA): A satiety hormone that regulates food intake.
* Palmitoylethanolamide (PEA): A potent anti-inflammatory and analgesic agent.
The N-acylethanolamine metabolic process is a complex and dynamic system that plays a critical role in health and disease. Further research is needed to elucidate the intricate mechanisms involved in NAE biosynthesis, degradation, signaling, and regulation.'
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Proteins (2)
| Protein | Definition | Taxonomy |
|---|---|---|
| N-acyl-phosphatidylethanolamine-hydrolyzing phospholipase D | An N-acyl-phosphatidylethanolamine-hydrolyzing phospholipase D that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q6IQ20] | Homo sapiens (human) |
| N-acylethanolamine-hydrolyzing acid amidase | An N-acylethanolamine-hydrolyzing acid amidase that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q02083] | Homo sapiens (human) |
Compounds (14)
| Compound | Definition | Classes | Roles |
|---|---|---|---|
| cannabinol | Cannabinol: A physiologically inactive constituent of Cannabis sativa L. | dibenzopyran | |
| hexachlorophene | hexachlorophene : An organochlorine compound that is diphenylmethane in which each of the phenyl groups is substituted by chlorines at positions 2, 3, and 5, and by a hydroxy group at position 6. An antiseptic that is effective against Gram-positive organisms, it is used in soaps and creams for the treatment of various skin disorders. It is also used in agriculture as an acaricide and fungicide, but is not approved for such use within the European Union. Hexachlorophene: A chlorinated bisphenol antiseptic with a bacteriostatic action against Gram-positive organisms, but much less effective against Gram-negative organisms. It is mainly used in soaps and creams and is an ingredient of various preparations used for skin disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p797) | bridged diphenyl fungicide; polyphenol; trichlorobenzene | acaricide; antibacterial agent; antifungal agrochemical; antiseptic drug |
| lithocholic acid | lithocholate : A bile acid anion that is the conjugate base of lithocholic acid. lithocholic acid : A monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action. Lithocholic Acid: A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic. | bile acid; C24-steroid; monohydroxy-5beta-cholanic acid | geroprotector; human metabolite; mouse metabolite |
| diacerein | diacerein: chelates with bivalent metals; a quinone which possesses redox properties; metabolized to active rhein; proposed mechanisms include inhibiting IL1 and metalloproteinases; called a slow acting symptomatic drug in osteoarthritis; no effect of cyclooxygenase; | anthraquinone | |
| cannabichromene | 1-benzopyran | ||
| (6ar-trans)-isomer of tetrahydrocannabivarin 9 | |||
| delta(9)-tetrahydrocannabinolic acid | Delta(9)-tetrahydrocannabinolic acid : A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant. | benzochromene; diterpenoid; hydroxy monocarboxylic acid; phytocannabinoid; polyketide | anti-inflammatory agent; biomarker; metabolite; neuroprotective agent |
| cannabidiolic acid | cannabidiolic acid : A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a 3-p-mentha-1,8-dien-3-yl (limonene) group. cannabidiolic acid: structure | dihydroxybenzoic acid; phytocannabinoid; polyketide; resorcinols | |
| sc 58272 | SC 58272: inhibits myristoyl-CoA:protein N-myristoyltransferase; structure given in first source | ||
| cannabidiol | cannabidiol : An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4. Cannabidiol: Compound isolated from Cannabis sativa extract. | olefinic compound; phytocannabinoid; resorcinols | antimicrobial agent; plant metabolite |
| cannabigerol | cannabigerol : A member of the class of resorcinols that is resorcinol which is substituted by a (2E)-3,7-dimethylocta-2,6-dien-1-yl group at position 2 and by a pentyl group at position 5. It is a natural product found in Cannabis sativa and Helichrysum species. cannabigerol: RN given refers to (E)-isomer; structure given in first source | phytocannabinoid; resorcinols | anti-inflammatory agent; antibacterial agent; antioxidant; appetite enhancer; cannabinoid receptor agonist; neuroprotective agent; plant metabolite |
| nitrocefin | nitrocefin: chromogenic cephalosporin used for detection of beta-lactamase activity; Cefinase is name for nitrocefin on paper disc; RN given refers to (6R-(3(E),6 alpha,7 beta))-isomer; structure for mono-Na salt in second source | ||
| cannabigerolic acid | cannabigerolic acid : A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant. cannabigerolic acid: structure in first source | dihydroxybenzoic acid; diterpenoid; phytocannabinoid; polyketide; resorcinols | |
| cannabidivarin | cannabidivarin: from Cannabis sativa | monoterpenoid |