N8-Acetylspermidine (ECMDB21254) (M2MDB001662)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (1)
Record Information
Version2.0
Creation Date2012-07-30 14:55:07 -0600
Update Date2015-09-13 15:15:31 -0600
Secondary Accession Numbers
  • ECMDB21254
Identification
Name:N8-Acetylspermidine
DescriptionN8-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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • N-[4-(3-Aminopropylamino)butyl]acetamide
  • N-[4-[(3-Aminopropyl)amino]butyl]-Acetamide
  • N-{4-[(3-Aminopropyl)amino]butyl}acetamide
  • N8-Acetylspermidine
  • N8-monoacetylspermidine
Chemical Formula:C9H21N3O
Weight:Average: 187.2825
Monoisotopic: 187.168462309
InChI Key:FONIWJIDLJEJTL-UHFFFAOYSA-N
InChI:InChI=1S/C9H21N3O/c1-9(13)12-8-3-2-6-11-7-4-5-10/h11H,2-8,10H2,1H3,(H,12,13)
CAS number:13431-24-8
IUPAC Name:N-{4-[(3-aminopropyl)amino]butyl}acetamide
Traditional IUPAC Name:N8-acetylspermidine
SMILES:CC(=O)NCCCCNCCCN
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:202-203 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.4 g/LALOGPS
logP-0.48ALOGPS
logP-1.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)16.53ChemAxon
pKa (Strongest Basic)10.29ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area67.15 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity54.41 m³·mol⁻¹ChemAxon
Polarizability23.1 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 > Coenzyme A + Hydrogen ion + N8-Acetylspermidine
SMPDB Pathways:
S-adenosyl-L-methionine biosynthesisPW000837 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9200000000-7350029bbf7fca576698View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-d04fb233b228bfc46b79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01w0-0900000000-e68fd1aa92642ae4208dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03k9-7900000000-287b3decd26c7daeb830View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0089-9100000000-e42a1f8955afadd5f50dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0089-9000000000-b18801afe8921946e40fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03k9-4900000000-fc04b14a414610552acdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-ed4e22e75d7e4ab076e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052o-5900000000-f486a2117b1dd060f58eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-dd7c2661d7b6091c7766View 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, Negativesplash10-052r-6900000000-9ecb44c4262e0df34ea4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-078ef81a1628477a273fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-009j-1900000000-ec737abcda867c6557b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-6900000000-c57d66a60207b42d5604View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9100000000-5e4ff8c1235fb203f05fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-3aacf768b87a62171bf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-9600000000-8855f267bbadb8cff170View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9100000000-286ce82869d4963e80f9View 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
  • Hrushesky WJ, Merdink J, Abdel-Monem MM: Circadian rhythmicity of polyamine urinary excretion. Cancer Res. 1983 Aug;43(8):3944-7. Pubmed: 6861156
  • 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
  • Mudumba S, Menezes A, Fries D, Blankenship J: Differentiation of PC12 cells induced by N8-acetylspermidine and by N8-acetylspermidine deacetylase inhibition. Biochem Pharmacol. 2002 Jun 1;63(11):2011-8. Pubmed: 12093478
  • 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
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
External Links:
ResourceLink
CHEBI ID27911
HMDB IDHMDB02189
Pubchem Compound ID123689
Kegg IDC01029
ChemSpider ID110264
Wikipedia IDNot Available
BioCyc IDCPD-3462
EcoCyc IDCPD-3462
Ligand ExpoQ9C

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.