N8-Acetylspermidine (CHEM021643)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:09:00 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021643
Identification
Common NameN8-Acetylspermidine
ClassSmall Molecule
DescriptionAn acetylspermidine that is 1,8-diamino-4-azaoctane in which one of the hydrogens of the amino group attached to C-8 is replaced by an acetyl group.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N(8)-MonoacetylspermidineChEBI
N-[4-[(3-Aminopropyl)amino]butyl]-acetamideHMDB
N(8)-Acetylspermidine dihydrochlorideMeSH, HMDB
N(8)-AcetylspermidineMeSH, HMDB
N-[4-[(3-Aminopropyl)amino]butyl]acetamideHMDB
N8-AcetylspermidineHMDB
N8-MonoacetylspermidineHMDB
Chemical FormulaC9H21N3O
Average Molecular Mass187.283 g/mol
Monoisotopic Mass187.168 g/mol
CAS Registry Number34450-15-2
IUPAC NameN-{4-[(3-aminopropyl)amino]butyl}acetamide
Traditional NameN8-acetylspermidine
SMILESCC(=O)NCCCCNCCCN
InChI IdentifierInChI=1S/C9H21N3O/c1-9(13)12-8-3-2-6-11-7-4-5-10/h11H,2-8,10H2,1H3,(H,12,13)
InChI KeyFONIWJIDLJEJTL-UHFFFAOYSA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9200000000-7350029bbf7fca576698Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-d04fb233b228bfc46b79Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01w0-0900000000-e68fd1aa92642ae4208dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03k9-7900000000-287b3decd26c7daeb830Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0089-9100000000-e42a1f8955afadd5f50dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0089-9000000000-b18801afe8921946e40fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03k9-4900000000-fc04b14a414610552acdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-ed4e22e75d7e4ab076e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052o-5900000000-f486a2117b1dd060f58eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-dd7c2661d7b6091c7766Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-b573184691a2508c0c96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-6900000000-9ecb44c4262e0df34ea4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-078ef81a1628477a273fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-009j-1900000000-ec737abcda867c6557b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-6900000000-c57d66a60207b42d5604Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9100000000-5e4ff8c1235fb203f05fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-3aacf768b87a62171bf0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-9600000000-8855f267bbadb8cff170Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9100000000-286ce82869d4963e80f9Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002189
FooDB IDFDB022894
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-3462
METLIN ID6535
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID110264
ChEBI ID27911
PubChem Compound ID123689
Kegg Compound IDC01029
YMDB IDYMDB00329
ECMDB IDECMDB21254
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12093478
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=6473353
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=894508
4. 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.
5. 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.
6. Hrushesky WJ, Merdink J, Abdel-Monem MM: Circadian rhythmicity of polyamine urinary excretion. Cancer Res. 1983 Aug;43(8):3944-7.
7. 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.
8. 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.
9. 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.
10. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3.
11. 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.