Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:49:01 -0600 |
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Update Date | 2015-09-13 15:15:22 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | N1-Acetylspermidine |
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Description | N1-acetylspermidine is a member of the chemical class known as Secondary Carboxylic Acid Amides. These are compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl). Acetylspermidine is an osmoprotectant. Heat shock, cold shock, ethanol, and alkaline shift stimulate the accumulation of Acetylspermidine in Escherichia coli. This compound is generated by Spermidine acetyltransferase (SAT) which is a tetramer of 4 identical subunits that catlyzes the reaction of acetyl-CoA with spermidine. |
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Structure | |
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Synonyms: | - 1-N-Acetylspermidine
- An N-acetylspermidine
- An N-acetylspermidine
- N(1)-Acetylspermidine
- N-(3-((4-Aminobutyl)amino)propyl)-Acetamide
- N-(3-((4-Aminobutyl)amino)propyl)acetamide
- N-Acetylspermidine
- N1-Acetylspermidine
- N1AcSpermidine
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Chemical Formula: | C9H21N3O |
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Weight: | Average: 187.2825 Monoisotopic: 187.168462309 |
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InChI Key: | MQTAVJHICJWXBR-UHFFFAOYSA-N |
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InChI: | InChI=1S/C9H21N3O/c1-9(13)12-8-4-7-11-6-3-2-5-10/h11H,2-8,10H2,1H3,(H,12,13) |
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CAS number: | 14278-49-0 |
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IUPAC Name: | N-{3-[(4-aminobutyl)amino]propyl}acetamide |
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Traditional IUPAC Name: | N1-acetylspermidine |
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SMILES: | CC(=O)NCCCNCCCCN |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group). |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboximidic acids and derivatives |
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Sub Class | Carboximidic acids |
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Direct Parent | Carboximidic acids |
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Alternative Parents | |
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Substituents | - Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Secondary amine
- Secondary aliphatic amine
- Carboximidic acid
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Amine
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Solid |
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Charge: | 2 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | Not Available |
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Concentration | Strain | Media | Growth Status | Growth System | Temperature | Details |
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430± 0 uM | K12 HB101 | 199 Medium with Earle’s salts –which contains 21 amino acids, 17 vitamins, 10 components of nucleic acids, sodium acetate, glucose, NaC1, KCl, CaC12, MgS04, Na2HP04, and Fe(N03)3 | Mid Log Phase | Shake flask | 37 oC | PMID: 8742354 | 30± 0 uM | K12 HB101 | 199 Medium with Earle’s salts –which contains 21 amino acids, 17 vitamins, 10 components of nucleic acids, sodium acetate, glucose, NaC1, KCl, CaC12, MgS04, Na2HP04, and Fe(N03)3 | Stationary Phase | Shake flask | 37 oC | PMID: 8742354 |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00ec-9300000000-435442e25431afc9ca94 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00g1-1900000000-25a42a25b21ff785892b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05dj-6900000000-12de75772a08ca08852a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fu-9200000000-2dfa5d648a84baff3e54 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-1900000000-90283b76b9478101a593 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052o-5900000000-4cac7a34f5b572449747 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9000000000-46e81717ccd7a43b7c55 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0079-3900000000-7dcca0a83898d18d48ff | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ab9-9300000000-db42164e7ae02cc3565e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05gi-9000000000-b73b9a6524aaa490eb70 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-b573184691a2508c0c96 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4r-9700000000-683029d89d5350729ba4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9000000000-236e795417fce314ee2b | View in MoNA |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - 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
- Hamana, K. (1996). "Distribution of diaminopropane and acetylspermidine in Enterobacteriaceae." Can J Microbiol 42:107-114. Pubmed: 8742354
- Hrushesky WJ, Merdink J, Abdel-Monem MM: Circadian rhythmicity of polyamine urinary excretion. Cancer Res. 1983 Aug;43(8):3944-7. Pubmed: 6861156
- Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
- 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
- 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
- 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
- van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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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. |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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