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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:40 UTC
Update Date2020-02-26 21:23:54 UTC
HMDB IDHMDB0002189
Secondary Accession Numbers
  • HMDB0060288
  • HMDB02189
  • HMDB60288
Metabolite Identification
Common 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. 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. 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 ).
Structure
Data?1582752234
Synonyms
ValueSource
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
Chemical FormulaC9H21N3O
Average Molecular Weight187.2825
Monoisotopic Molecular Weight187.168462309
IUPAC NameN-{4-[(3-aminopropyl)amino]butyl}acetamide
Traditional NameN8-acetylspermidine
CAS Registry Number13431-24-8
SMILES
CC(=O)NCCCCNCCCN
InChI Identifier
InChI=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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point202 - 203 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9200000000-7350029bbf7fca576698Spectrum
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
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, 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
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.05 +/- 0.014 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified0.0437 +/- 0.129 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.136 +/- 0.190 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.150 +/- 0.0787 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.178 +/- 0.156 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
UrineDetected and Quantified1.04 +/- 0.3 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.30 (0.15-0.65) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.271 +/- 0.187 umol/mmol creatinineAdult (>18 years old)BothNot Available details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.22 +/- 0.02 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.063 +/- 0.03 uMAdult (>18 years old)FemaleBreast cancer details
UrineDetected and Quantified0.2 +/- 0.24 umol/mmol creatinineAdult (>18 years old)FemaleBreast cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothLeukemia details
UrineDetected and Quantified0.394 +/- 0.156 umol/mmol creatinineAdult (>18 years old)BothLeukemia details
UrineDetected and Quantified0.88 +/- 0.14 umol/mmol creatinineAdult (>18 years old)BothPancreatic cancer details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Byun JA, Lee SH, Jung BH, Choi MH, Moon MH, Chung BC: Analysis of polyamines as carbamoyl derivatives in urine and serum by liquid chromatography-tandem mass spectrometry. Biomed Chromatogr. 2008 Jan;22(1):73-80. [PubMed:17668437 ]
Thyroid cancer
  1. Loser C, Folsch UR, Paprotny C, Creutzfeldt W: Polyamine concentrations in pancreatic tissue, serum, and urine of patients with pancreatic cancer. Pancreas. 1990 Mar;5(2):119-27. [PubMed:2315288 ]
Leukemia
  1. Lee SH, Suh JW, Chung BC, Kim SO: Polyamine profiles in the urine of patients with leukemia. Cancer Lett. 1998 Jan 9;122(1-2):1-8. [PubMed:9464484 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022894
KNApSAcK IDNot Available
Chemspider ID110264
KEGG Compound IDC01029
BioCyc IDCPD-3462
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6535
PubChem Compound123689
PDB IDNot Available
ChEBI ID27911
Food Biomarker OntologyNot Available
VMH IDN8ASPMD
References
Synthesis ReferenceTabor, 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
General References
  1. Hrushesky WJ, Merdink J, Abdel-Monem MM: Circadian rhythmicity of polyamine urinary excretion. Cancer Res. 1983 Aug;43(8):3944-7. [PubMed:6861156 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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. [PubMed:23455439 ]
  6. 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 ]