Record Information
Version1.0
Creation date2011-09-21 00:21:15 UTC
Update date2019-11-26 03:21:06 UTC
Primary IDFDB022894
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN8-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. This acetyltransferase appears to be associated with chromatin in the cell nucleus and has been reported to be the same as (or related to) the enzyme(s) responsible for histone acetylation. N8-Acetylspermidine does not accumulate in tissues but rather appears to be rapidly deacetylated back to spermidine by a relatively specific cytosolic deacetylase, N8-acetylspermidine deacetylase. The function of this N8-acetylation/deacetylation pathway in cellular processes is not understood clearly, but several observations have suggested a role in cell growth and differentiation. (PMID: 12093478) [HMDB]
CAS Number34450-15-2
Structure
Thumb
Synonyms
SynonymSource
N(8)-MonoacetylspermidineChEBI
N-[4-[(3-Aminopropyl)amino]butyl]-acetamideHMDB
N(8)-Acetylspermidine dihydrochlorideHMDB
N(8)-AcetylspermidineHMDB
N-[4-[(3-Aminopropyl)amino]butyl]acetamideHMDB
N8-MonoacetylspermidineHMDB
N8-AcetylspermidineHMDB
N-[4-[(3-aminopropyl)amino]butyl]-Acetamidehmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H21N3O
IUPAC nameN-{4-[(3-aminopropyl)amino]butyl}acetamide
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
Isomeric SMILESCC(=O)NCCCCNCCCN
Average Molecular Weight187.2825
Monoisotopic Molecular Weight187.168462309
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSN8-Acetylspermidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001l-9200000000-7350029bbf7fca576698Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-d04fb233b228bfc46b79Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01w0-0900000000-e68fd1aa92642ae4208dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03k9-7900000000-287b3decd26c7daeb830Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0089-9100000000-e42a1f8955afadd5f50dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0089-9000000000-b18801afe8921946e40fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-009j-1900000000-ec737abcda867c6557b2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-6900000000-c57d66a60207b42d5604Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9100000000-5e4ff8c1235fb203f05fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-ed4e22e75d7e4ab076e2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052o-5900000000-f486a2117b1dd060f58eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-dd7c2661d7b6091c7766Spectrum
NMRNot Available
ChemSpider ID110264
ChEMBL IDCHEMBL78630
KEGG Compound IDC01029
Pubchem Compound ID123689
Pubchem Substance IDNot Available
ChEBI ID27911
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB60288
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference