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N1-Acetylspermidine (M2MDB000322)

Record Information
Version2.0
Creation Date2012-05-31 13:49:01 -0600
Update Date2015-09-13 15:15:22 -0600
Secondary Accession Numbers
  • ECMDB01276
Identification
Name:N1-Acetylspermidine
DescriptionN1-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.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
Chemical Formula:C9H21N3O
Weight:Average: 187.2825
Monoisotopic: 187.168462309
InChI Key:MQTAVJHICJWXBR-UHFFFAOYSA-N
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)
CAS number:14278-49-0
IUPAC Name:N-{3-[(4-aminobutyl)amino]propyl}acetamide
Traditional IUPAC Name:N1-acetylspermidine
SMILES:CC(=O)NCCCNCCCCN
Chemical Taxonomy
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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
Sub ClassCarboximidic acids
Direct ParentCarboximidic acids
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-0.342PhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.72 g/LALOGPS
logP-0.47ALOGPS
logP-1.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)16.53ChemAxon
pKa (Strongest Basic)10.67ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area67.15 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity54.41 m³·mol⁻¹ChemAxon
Polarizability23.11 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Acetyl-CoA + Spermidine > N1-Acetylspermidine + Coenzyme A + Hydrogen ion
Acetyl-CoA + Spermidine <> N1-Acetylspermidine + Hydrogen ion + Coenzyme A
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
430± 0 uMK12 HB101199 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)3Mid Log PhaseShake flask37 oCPMID: 8742354
30± 0 uMK12 HB101199 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)3Stationary PhaseShake flask37 oCPMID: 8742354
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ec-9300000000-435442e25431afc9ca94View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00g1-1900000000-25a42a25b21ff785892bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05dj-6900000000-12de75772a08ca08852aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9200000000-2dfa5d648a84baff3e54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-90283b76b9478101a593View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052o-5900000000-4cac7a34f5b572449747View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-46e81717ccd7a43b7c55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-3900000000-7dcca0a83898d18d48ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9300000000-db42164e7ae02cc3565eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05gi-9000000000-b73b9a6524aaa490eb70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-b573184691a2508c0c96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9700000000-683029d89d5350729ba4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-236e795417fce314ee2bView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
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
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
External Links:
ResourceLink
CHEBI ID17927
HMDB IDHMDB01276
Pubchem Compound ID496
Kegg IDC00612
ChemSpider ID482
Wikipedia IDNot Available
BioCyc IDCPD-568
EcoCyc IDCPD-568

Enzymes

Protein Details
1. Spermidine N(1)-acetyltransferase
General function:
Involved in N-acetyltransferase activity
Specific function:
Regulates polyamine concentration by their degradation. Acts on spermidine, forming N(1)- and N(8)-acetylspermidine
Gene Name:
speG
Uniprot ID:
P0A951
Molecular weight:
21887
Reactions
Acetyl-CoA + an alkane-alpha,omega-diamine = CoA + an N-acetyldiamine.