Human Metabolome Database Version 3.5

Showing metabocard for N1-Acetylspermidine (HMDB01276)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:31:04 -0600
HMDB ID HMDB01276
Secondary Accession Numbers None
Metabolite Identification
Common Name N1-Acetylspermidine
Description N1-Acetylspermidine is a polyamine. In many organisms, polyamines originate from L-ornithine and methionine. Ornithine decarboxylase (EC 4.1.1.17), a key enzyme in polyamine metabolism, decarboxylates L-ornithine to yield putrescine which is then converted to higher polyamines spermidine and spermine by successive addition of aminopropyl groups derived from decarboxylated S-adenosylmethionine. Aliphatic polyamines occur ubiquitously in organisms and have important functions in the stabilization of cell membranes, biosynthesis of informing molecules, cell growth and differentiation, as well as adaptation to osmotic, ionic, pH and thermal stress. These cationic substances are implicated in multiple functions, therefore it is not surprising that intracellular levels of polyamines are regulated by different mechanisms. The inhibition of polyamine metabolism has important pharmacological and therapeutic implications for the control of physiological processes, reproduction, cancer and parasitic diseases. Recent reports have suggested the idea that parasites with an high turnover of Ornithine Decarboxilase (ODC) are resistant to Difluoromethyl ornithine (DFMO, the irreversible inhibitor of ornithine decarboxylase) because they always contain a fraction of newly synthesized and active enzyme, therefore not DFMO inhibited, sufficient to produce small amounts of putrescine rapidly converted into spermidine, which can support protozoan proliferation. DFMO has proved to be curative in trypanosomiasis, coccidiosis, and certain other protozoan infections. (PMID: 15490259 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-N-Acetylspermidine
  2. An N-acetylspermidine
  3. N(1)-Acetylspermidine
  4. N-(3-((4-Aminobutyl)amino)propyl)-Acetamide
  5. N-(3-((4-Aminobutyl)amino)propyl)acetamide
  6. N-Acetylspermidine
  7. N1-Acetylspermidine
Chemical Formula C9H21N3O
Average Molecular Weight 187.2825
Monoisotopic Molecular Weight 187.168462309
IUPAC Name N-{3-[(4-aminobutyl)amino]propyl}acetamide
Traditional IUPAC Name N(1)-acetylspermidine
CAS Registry Number 14278-49-0
SMILES CC(=O)NCCCNCCCCN
InChI Identifier InChI=1S/C9H21N3O/c1-9(13)12-8-4-7-11-6-3-2-5-10/h11H,2-8,10H2,1H3,(H,12,13)
InChI Key MQTAVJHICJWXBR-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
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available 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 4.72 g/L ALOGPS
LogP -0.47 ALOGPS
LogP -1.3 ChemAxon
LogS -1.60 ALOGPS
pKa (strongest acidic) 16.53 ChemAxon
pKa (strongest basic) 10.67 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 23.11 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.007 +/- 0.002 uM Adult (>18 years old) Female Normal
Urine Detected and Quantified
0.39 (0.12-0.72) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.199 +/- 0.142 umol/mmol creatinine Adult (>18 years old) Both Not Available
Urine Detected and Quantified
0.0045 +/- 0.005 umol/mmol creatinine Adult (>18 years old) Female Normal
Urine Detected and Quantified
0.38 +/- 0.033 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.0056 +/- 0.0027 uM Adult (>18 years old) Female Breast cancer
Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Leukemia
Urine Detected and Quantified 1.03 +/- 0.693 umol/mmol creatinine Adult (>18 years old) Both Leukemia
Urine Detected and Quantified 0.0011 +/- 0.003 umol/mmol creatinine Adult (>18 years old) Female Breast cancer
Urine Detected and Quantified 1.9 +/- 0.35 umol/mmol creatinine Adult (>18 years old) Both Pancreatic cancer
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
          DrugBank Metabolite ID Not Available
          Phenol Explorer Compound ID Not Available
          Phenol Explorer Metabolite ID Not Available
          FoodDB ID FDB022530
          KNApSAcK ID Not Available
          Chemspider ID 482 Link_out
          KEGG Compound ID C00612 Link_out
          BioCyc ID CPD-568 Link_out
          BiGG ID Not Available
          Wikipedia Link Not Available
          NuGOwiki Link HMDB01276 Link_out
          Metagene Link HMDB01276 Link_out
          METLIN ID 3323 Link_out
          PubChem Compound 496 Link_out
          PDB ID Not Available
          ChEBI ID 17927 Link_out
          References
          Synthesis Reference Lurdes M; Almeida S; Grehn L; Ragnarsson U Facile synthesis of monoacetylated spermidines, illustrating selective deacetylation and application of a common precursor. Acta chemica Scandinavica (Copenhagen, Denmark : 1989) (1989), 43(10), 990-4.
          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. Smith RG, Bartos D, Bartos F, Grettie DP, Frick W, Campbell RA, Daves GD Jr: 1-N-Acetylspermidine: occurrence in normal human serum. Biomed Mass Spectrom. 1978 Sep;5(9):515-7. Pubmed: 708851 Link_out
          5. Ruggeri P, Lagana G, Bellocco E, Fabiano C, Leonaldi R, Forino D: Polyamines biosynthesis and oxidation in free-living amoebae. Amino Acids. 2004 Dec;27(3-4):367-72. Epub 2004 Oct 15. Pubmed: 15490259 Link_out

          Enzymes
          Name: Diamine acetyltransferase 2
          Reactions: Not Available
          Gene Name: SAT2
          Uniprot ID: Q96F10 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Diamine acetyltransferase 1
          Reactions: Not Available
          Gene Name: SAT1
          Uniprot ID: P21673 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Peroxisomal N(1)-acetyl-spermine/spermidine oxidase
          Reactions:
          N1-Acetylspermidine + Oxygen + Water unknown Putrescine + Acetamidopropanal + Hydrogen peroxide details
          N1,N12-Diacetylspermine + Oxygen + Water unknown N1-Acetylspermidine + 3-Acetamidobutanal + Hydrogen peroxide details
          Gene Name: PAOX
          Uniprot ID: Q6QHF9 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA