General Information of MET (ID: META00471)
Name Palmitoylethanolamide
Synonyms   Click to Show/Hide Synonyms of This Metabolite
Anandamide (16:0); Hexadecanoyl ethanolamide; Hydroxyethylpalmitamide; Impulsin; Loramine p 256; MimyX; Monoethanolamine palmitate amide; Monoethanolamine palmitic acid amide; N-(2-Hydroxyethyl)hexadecanamide; N-(2-Hydroxyethyl)palmitamide; N-(2-Hydroxyethyl)palmitate; N-Hexadecanoyl ethanolamine; N-Hexadecanoylethanolamine; N-Hexadecyl-ethanolamine; N-Palmitoylethanolamine; PEA; Palmdrol prodes; Palmidrol; Palmidrolum; Palmitamide mea; Palmitate monoethanolamide; Palmitic acid monoethanolamide; Palmitinsaeure-beta-hydroxyethylamid; Palmitoyl ethanolamide; Palmitoyl-ea; Palmitoylethanolamide; Palmitylethanolamide
Source Endogenous;Fatty acyls;Food
Structure Type   Carboximidic acids  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboximidic acids and derivatives
Carboximidic acids
PubChem CID
4671
HMDB ID
HMDB0002100
Formula
C18H37NO2
Structure
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3D MOL is unavailable 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C16512
ChEBI ID
71464
FooDB ID
FDB001087
ChemSpider ID
4509
Physicochemical Properties Molecular Weight 299.5 Topological Polar Surface Area 49.3
XlogP 6.2 Complexity 219
Heavy Atom Count 21 Rotatable Bond Count 16
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Function
N-Palmitoylethanolamide (PEA) is present in the tissues of most mammals. It was initially described as an agonist of the type 2 cannabinoid receptor (CB2), although it is now universally recognized that PEA is in fact incapable of binding to cannabinoid receptors, or at least not to the known receptors. In addition to its anti-inflammatory activity, PEA also produces analgesia, neuroprotection, and possesses anti-epileptic properties. It also reduces gastrointestinal motility and cancer cell proliferation, as well as protecting the vascular endothelium in the ischemic heart. The physiological stimuli that regulate PEA levels in mammalian tissues are largely unknown, however, multiple studies indicate that this lipid accumulates during cellular stress, particularly following tissue injury. For example, PEA increases post-mortem in the pig brain. Similar elevations in PEA levels have been observed in the ischemic brain and PEA is also up-regulated in response to ultraviolet-B irradiation in mouse epidermal cells. Adipose tissue is highly implicated in the systemic secretion of IL-6 and leptin, and human mature adipocytes are able to secrete large quantity of PEA. Human adipose tissue can be subjected to modulation of its inflammatory state by lipopolysaccharide (LPS). LPS strongly inhibits adipose cell leptin release, with PEA acting as a potentiator of this inhibitory effect. These actions are not linked to a reduction in leptin gene transcription. Thus, PEA does not have an anti-inflammatory role in the secretion of IL-6 via NFkappaB at the adipocyte level, but instead seems to act at the heart of the LPS-stimulated pathway, which, independently of NFkappaB, inhibits the secretion of leptin.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transferases (EC 2)
            Carnitine O-palmitoyltransferase 1 (CPT1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of Cpt1c
                      Induced Change Palmitoylethanolamide concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Cpt1c leads to the decrease of palmitoylethanolamide levels compared with control group.
References
1 Metabolomic profiling reveals a role for CPT1c in neuronal oxidative metabolism. BMC Biochem. 2012 Oct 25;13:23.

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