Details of Metabolite

General Information of MET (ID: META00649)
Name Palmitoleoylethanolamde
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(9Z)-N-(2-Hydroxyethyl)-9-hexadecenamide; (Z)-Hexadec-9-enoyl ethanolamide; N-(2-Hydroxyethyl)palmitoleylamide; N-(9Z-Hexadecenoyl) ethanolamine; N-(9Z-Hexadecenoyl)-ethanolamide; N-(9Z-Hexadecenoyl)-ethanolamine; POEA; Palmitoleoyl ethanolamide; Palmitoleoyl-ea; Palmitoleoyl-ethanolamide; Palmitoleoyl-ethanolamine; Polyoxyethyleneamine
Source Endogenous;Fatty acyls;Food
Structure Type   Amines  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic nitrogen compounds
Organonitrogen compounds
Amines
PubChem CID
9835868
HMDB ID
HMDB0013648
Formula
C18H35NO2
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
ChEBI ID
71465
FooDB ID
FDB029618
ChemSpider ID
8011589
Physicochemical Properties Molecular Weight 297.5 Topological Polar Surface Area 49.3
XlogP 5.3 Complexity 252
Heavy Atom Count 21 Rotatable Bond Count 15
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Function
Palmitoleoylethanolamde (POEA), belongs to the class of organic compounds known as N-acylethanolamines. N-Acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine. Thus, palmitoleoylethanolamde is considered to be a fatty amide lipid molecule. Palmitoleoylethanolamde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. During abstinence, young adults with a history of alcohol binge drinking had elevated plasma levels of monounsaturated and polyunsaturatedacylethanolamides, specifically oleoylethanolamide (OEA), palmitoleoylethanolamide (POEA), arachidonoylethanolamide (AEA), and dihomo-gamma-linolenoylethanolamide (DGLEA). Changes in these lipids positively correlated with mRNA upregulation of inflammatory markers in peripheral blood mononuclear cells (PBMCs), such as toll-like receptors (TLR4), pro-inflammatory cytokines/chemokines, and cyclooxygenase-2.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transferases (EC 2)
            Arylamine N-acetyltransferase 1 (NAT1) 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 NAT1
                      Induced Change Palmitoleoylethanolamde concentration: increase (FC = 3)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Breast cancer [ICD-11: 2C60]
                      Details It is reported that knockout of NAT1 leads to the increase of palmitoleoylethanolamde levels compared with control group.
References
1 CRISPR/Cas9 knockout of human arylamine N-acetyltransferase 1 in MDA-MB-231 breast cancer cells suggests a role in cellular metabolism. Sci Rep. 2020 Jun 17;10(1):9804.

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