General Information of MET (ID: META00475)
Name N8-Acetylspermidine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
N(8)-Acetylspermidine; N(8)-Acetylspermidine dihydrochloride; N(8)-Monoacetylspermidine; N-[4-[(3-Aminopropyl)amino]butyl]-acetamide; N-[4-[(3-Aminopropyl)amino]butyl]acetamide; N8-Acetylspermidine; N8-Monoacetylspermidine
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;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
123689
HMDB ID
HMDB0002189
Formula
C9H21N3O
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C01029
ChEBI ID
27911
FooDB ID
FDB022894
ChemSpider ID
110264
METLIN ID
6535
Physicochemical Properties Molecular Weight 187.28 Topological Polar Surface Area 67.2
XlogP -0.8 Complexity 128
Heavy Atom Count 13 Rotatable Bond Count 8
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Function
N8-Acetylspermidine is a polyamine. The polyamines, found in virtually all living organisms, are a ubiquitous group of compounds that appear to play a vital role in many cellular processes involving nucleic acids including cell growth and differentiation. Acetylation on the terminal nitrogen adjacent to the 4-carbon chain produces N8-acetylspermidine. This reaction is catalyzed by spermidine N8-acetyltransferase and does not result in the conversion of spermidine to putrescine. Instead, the product undergoes deacetylation. This acetyltransferase appears to be associated with chromatin in the cell nucleus and has been reported to be the same as (or related to) the enzyme(s) responsible for histone acetylation. N8-Acetylspermidine does not accumulate in tissues but rather appears to be rapidly deacetylated back to spermidine by a relatively specific cytosolic deacetylase, N8-acetylspermidine deacetylase. The function of this N8-acetylation/deacetylation pathway in cellular processes is not understood clearly, but several observations have suggested a role in cell growth and differentiation.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Apolipoprotein (Apo)
            Apolipoprotein A-II (APOA2) 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 Mutation (-265T >C(rs5082)) of APOA2
                      Induced Change N8-Acetylspermidine concentration: decrease (FC = 0.80)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Obesity [ICD-11: 5B81]
                      Details It is reported that mutation (-265T >C(rs5082)) of APOA2 leads to the decrease of N8-acetylspermidine levels compared with control group.
References
1 Epigenomics and metabolomics reveal the mechanism of the APOA2-saturated fat intake interaction affecting obesity. Am J Clin Nutr. 2018 Jul 1;108(1):188-200.

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