Details of Metabolite

General Information of MET (ID: META00632)
Name Stearoylethanolamide
Synonyms   Click to Show/Hide Synonyms of This Metabolite
Monoethanolamine stearate amide; Monoethanolamine stearic acid amide; N-(2-Hydroxyethyl)stearamide; N-(2-Hydroxyethyl)stearoylamide; N-(Hydroxyethyl)stearamide; N-(Otadecanoyl)-ethanolamine; N-Octadecanoyl ethanolamine; N-Octadecanoylethanolamine; N-Stearoylethanolamine; Stearamide mea; Stearate monoethanolamide; Stearic acid monoethanolamide; Stearic ethanolamide; Stearic monoethanolamide; Stearoyl ethanolamide; Stearoyl-ea; Stearoyl-ethanolamine; Stearoylethanolamide; Stearoylmonoethanolamide
Source Endogenous;Fatty acyls;Food;Cosmetic
Structure Type   Amines  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic nitrogen compounds
Organonitrogen compounds
Amines
PubChem CID
27902
HMDB ID
HMDB0013078
Formula
C20H41NO2
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
85299
FooDB ID
FDB029286
ChemSpider ID
25958
Physicochemical Properties Molecular Weight 327.5 Topological Polar Surface Area 49.3
XlogP 7.3 Complexity 244
Heavy Atom Count 23 Rotatable Bond Count 18
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Function
Stearoylethanolamide 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 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.
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 Stearoylethanolamide concentration: increase (FC = 2.6)
                      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 stearoylethanolamide 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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