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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 08:07:06 UTC
HMDB IDHMDB0001276
Secondary Accession Numbers
  • HMDB01276
Metabolite Identification
Common NameN1-Acetylspermidine
DescriptionN1-Acetylspermidine is a polyamine. In many organisms, polyamines originate from L-ornithine and methionine. Ornithine decarboxylase (EC 4.1.1.17), a key enzyme in polyamine metabolism, decarboxylates L-ornithine to yield putrescine which is then converted to higher polyamines spermidine and spermine by successive addition of aminopropyl groups derived from decarboxylated S-adenosylmethionine. Aliphatic polyamines occur ubiquitously in organisms and have important functions in the stabilization of cell membranes, biosynthesis of informing molecules, cell growth and differentiation, as well as adaptation to osmotic, ionic, pH and thermal stress. These cationic substances are implicated in multiple functions, therefore it is not surprising that intracellular levels of polyamines are regulated by different mechanisms. The inhibition of polyamine metabolism has important pharmacological and therapeutic implications for the control of physiological processes, reproduction, cancer and parasitic diseases. Recent reports have suggested the idea that parasites with an high turnover of Ornithine Decarboxilase (ODC) are resistant to Difluoromethyl ornithine (DFMO, the irreversible inhibitor of ornithine decarboxylase) because they always contain a fraction of newly synthesized and active enzyme, therefore not DFMO inhibited, sufficient to produce small amounts of putrescine rapidly converted into spermidine, which can support protozoan proliferation. DFMO has proved to be curative in trypanosomiasis, coccidiosis, and certain other protozoan infections. (PMID: 15490259 ).
Structure
Thumb
Synonyms
ValueSource
1-N-AcetylspermidineChEBI
An N-acetylspermidineHMDB
N(1)-AcetylspermidineHMDB
N-(3-((4-Aminobutyl)amino)propyl)-acetamideHMDB
N-(3-((4-Aminobutyl)amino)propyl)acetamideHMDB
N-AcetylspermidineHMDB
Chemical FormulaC9H21N3O
Average Molecular Weight187.2825
Monoisotopic Molecular Weight187.168462309
IUPAC NameN-{3-[(4-aminobutyl)amino]propyl}acetamide
Traditional NameN1-acetylspermidine
CAS Registry Number14278-49-0
SMILES
CC(=O)NCCCNCCCCN
InChI Identifier
InChI=1S/C9H21N3O/c1-9(13)12-8-4-7-11-6-3-2-5-10/h11H,2-8,10H2,1H3,(H,12,13)
InChI KeyMQTAVJHICJWXBR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboximidic acids and derivatives
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:

  Health condition:

    Cancer:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.007 +/- 0.002 uMAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.39 (0.12-0.72) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
UrineDetected and Quantified0.199 +/- 0.142 umol/mmol creatinineAdult (>18 years old)BothNot Available details
UrineDetected and Quantified0.0045 +/- 0.005 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.38 +/- 0.033 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0056 +/- 0.0027 uMAdult (>18 years old)FemaleBreast cancer details
UrineDetected but not Quantified Adult (>18 years old)BothLeukemia details
UrineDetected and Quantified1.03 +/- 0.693 umol/mmol creatinineAdult (>18 years old)BothLeukemia details
UrineDetected and Quantified0.0011 +/- 0.003 umol/mmol creatinineAdult (>18 years old)FemaleBreast cancer details
UrineDetected and Quantified1.9 +/- 0.35 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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022530
KNApSAcK IDNot Available
Chemspider ID482
KEGG Compound IDC00612
BioCyc IDCPD-568
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3323
PubChem Compound496
PDB IDNot Available
ChEBI ID17927
References
Synthesis ReferenceLurdes 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
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. 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 ]
  5. 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 ]

Enzymes

General function:
Involved in N-acetyltransferase activity
Specific function:
Enzyme which catalyzes the acetylation of polyamines. Substrate specificity: norspermidine > spermidine = spermine >> N(1)acetylspermine = putrescine.
Gene Name:
SAT2
Uniprot ID:
Q96F10
Molecular weight:
19154.905
General function:
Involved in N-acetyltransferase activity
Specific function:
Enzyme which catalyzes the acetylation of polyamines. Substrate specificity: norspermidine = spermidine >> spermine > N(1)-acetylspermine > putrescine. This highly regulated enzyme allows a fine attenuation of the intracellular concentration of polyamines. Also involved in the regulation of polyamine transport out of cells. Acts on 1,3-diaminopropane, 1,5-diaminopentane, putrescine, spermidine (forming N(1)- and N(8)-acetylspermidine), spermine, N(1)-acetylspermidine and N(8)-acetylspermidine.
Gene Name:
SAT1
Uniprot ID:
P21673
Molecular weight:
20023.8
General function:
Amino acid transport and metabolism
Specific function:
Flavoenzyme which catalyzes the oxidation of N(1)-acetylspermine to spermidine and is thus involved in the polyamine back-conversion. Can also oxidize N(1)-acetylspermidine to putrescine. Substrate specificity: N(1)-acetylspermine = N(1)-acetylspermidine > N(1),N(12)-diacylspermine >> spermine. Does not oxidize spermidine. Plays an important role in the regulation of polyamine intracellular concentration and has the potential to act as a determinant of cellular sensitivity to the antitumor polyamine analogs.
Gene Name:
PAOX
Uniprot ID:
Q6QHF9
Molecular weight:
55512.64
Reactions
N1-Acetylspermidine + Oxygen + Water → Putrescine + Acetamidopropanal + Hydrogen peroxidedetails
N1,N12-Diacetylspermine + Oxygen + Water → N1-Acetylspermidine + 3-Acetamidobutanal + Hydrogen peroxidedetails