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Human Metabolome Database Version 3.5

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Showing metabocard for N8-Acetylspermidine (HMDB02189)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:40 -0600
Update Date 2013-02-08 17:11:32 -0700
HMDB ID HMDB02189
Secondary Accession Numbers None
Metabolite Identification
Common Name N8-Acetylspermidine
Description 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. 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 but, 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. (PMID: 12093478 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. N-[4-[(3-Aminopropyl)amino]butyl]-Acetamide
  2. N8-Acetylspermidine
Chemical Formula C9H21N3O
Average Molecular Weight 187.2825
Monoisotopic Molecular Weight 187.168462309
IUPAC Name N-{4-[(3-aminopropyl)amino]butyl}acetamide
Traditional IUPAC Name N(8)-acetylspermidine
CAS Registry Number 34450-15-2
SMILES CC(=O)NCCCCNCCCN
InChI Identifier InChI=1S/C9H21N3O/c1-9(13)12-8-3-2-6-11-7-4-5-10/h11H,2-8,10H2,1H3,(H,12,13)
InChI Key FONIWJIDLJEJTL-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Carboxylic Acids and Derivatives
Sub Class Carboxylic Acid Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • acetylspermidine(ChEBI)
Substituents
  • Polyamine
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Aliphatic Amine (Dialkylamine)
Direct Parent Secondary Carboxylic Acid Amides
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 202 - 203 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 4.4 g/L ALOGPS
LogP -0.48 ALOGPS
LogP -1.3 ChemAxon
LogS -1.63 ALOGPS
pKa (strongest acidic) 16.53 ChemAxon
pKa (strongest basic) 10.59 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 67.15 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 54.41 ChemAxon
Polarizability 23.1 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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0.05 +/- 0.014 uM Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
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1.04 +/- 0.3 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
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0.30 (0.15-0.65) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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0.22 +/- 0.02 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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0.063 +/- 0.03 uM Adult (>18 years old) Female Breast cancer Not Available
Urine Detected and Quantified
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0.2 +/- 0.24 umol/mmol creatinine Adult (>18 years old) Female Breast cancer Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Leukemia Not Available
Urine Detected and Quantified
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0.88 +/- 0.14 umol/mmol creatinine Adult (>18 years old) Both Pancreatic cancer Not Available
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  • Byun JA, Lee SH, Jung BH, Choi MH, Moon MH, Chung BC: Analysis of polyamines as carbamoyl derivatives in urine and serum by liquid chromatography-tandem mass spectrometry. Biomed Chromatogr. 2008 Jan;22(1):73-80. Pubmed: 17668437 Link_out
    Thyroid cancer
    • Loser C, Folsch UR, Paprotny C, Creutzfeldt W: Polyamine concentrations in pancreatic tissue, serum, and urine of patients with pancreatic cancer. Pancreas. 1990 Mar;5(2):119-27. Pubmed: 2315288 Link_out
      Associated OMIM IDs None
      DrugBank ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB022894
      KNApSAcK ID Not Available
      Chemspider ID 110264 Link_out
      KEGG Compound ID C01029 Link_out
      BioCyc ID CPD-3462 Link_out
      BiGG ID Not Available
      Wikipedia Link Not Available
      NuGOwiki Link HMDB02189 Link_out
      Metagene Link HMDB02189 Link_out
      METLIN ID 6535 Link_out
      PubChem Compound 123689 Link_out
      PDB ID Q9C Link_out
      ChEBI ID 27911 Link_out
      References
      Synthesis Reference Tabor, Herbert; Tabor, Celia W.; De Meis, Leopold. Chemical synthesis of N-acetyl-1,4-diaminobutane, N1-acetylspermidine, and N8-acetylspermidine. Methods Enzymol. (1971), 17(Pt. B), 829-33.
      Material Safety Data Sheet (MSDS) Not Available
      General References
      1. Hrushesky WJ, Merdink J, Abdel-Monem MM: Circadian rhythmicity of polyamine urinary excretion. Cancer Res. 1983 Aug;43(8):3944-7. Pubmed: 6861156 Link_out
      2. Seiler N, Graham A, Bartholeyns J: Enhanced urinary excretion of N1-acetylspermidine and the presence of tumors. Cancer Res. 1981 Apr;41(4):1572-3. Pubmed: 6897929 Link_out
      3. Abdel-Monem MM, Merdink JL, Theologides A: Urinary excretion of monoacetyl polyamines in patients with non-Hodgkin's lymphoma. Cancer Res. 1982 May;42(5):2097-8. Pubmed: 7066912 Link_out
      4. Inoue H, Fukunaga K, Munemura S, Tsuruta Y: Simultaneous determination of free and N-acetylated polyamines in urine by semimicro high-performance liquid chromatography using 4-(5,6-dimethoxy-2-phthalimidinyl)-2-methoxyphenylsulfonyl chloride as a fluorescent labeling reagent. Anal Biochem. 2005 Apr 15;339(2):191-7. Pubmed: 15797558 Link_out