| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:10:14 -0700 |
| HMDB ID |
HMDB01276 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
N1-Acetylspermidine |
| Description |
N1-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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 1-N-Acetylspermidine
- An N-acetylspermidine
- N(1)-Acetylspermidine
- N-(3-((4-Aminobutyl)amino)propyl)-Acetamide
- N-(3-((4-Aminobutyl)amino)propyl)acetamide
- N-Acetylspermidine
- N1-Acetylspermidine
|
| Chemical Formula |
C9H21N3O |
| Average Molecular Weight |
187.2825 |
| Monoisotopic Molecular Weight |
187.168462309 |
| IUPAC Name |
N-{3-[(4-aminobutyl)amino]propyl}acetamide |
| Traditional IUPAC Name |
N(1)-acetylspermidine |
| CAS Registry Number |
14278-49-0 |
| 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 Key |
MQTAVJHICJWXBR-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Organic Acids and Derivatives |
| Class |
Carboxylic Acids and Derivatives |
| Sub Class |
Carboxylic Acid Derivatives |
| Other Descriptors |
- Aliphatic Acyclic Compounds
- Organic Compounds
- acetylspermidine(ChEBI)
|
| Substituents |
- Polyamine
- Primary Aliphatic Amine (Alkylamine)
- Secondary Aliphatic Amine (Dialkylamine)
|
| Direct Parent |
Secondary Carboxylic Acid Amides |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
|
| Tissue Location |
Not Available
|
| Pathways |
Not Available
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| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.007 +/- 0.002 uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.39 (0.12-0.72) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.0045 +/- 0.005 umol/mmol creatinine |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.38 +/- 0.033 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.0056 +/- 0.0027 uM |
Adult (>18 years old) |
Female |
Breast cancer |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Leukemia |
Not Available |
| Urine |
Detected and Quantified |
|
0.0011 +/- 0.003 umol/mmol creatinine |
Adult (>18 years old) |
Female |
Breast cancer |
Not Available |
| Urine |
Detected and Quantified |
|
1.9 +/- 0.35 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Pancreatic cancer |
Not Available |
|
| Associated Disorders and Diseases |
|---|
| Disease References |
| Perillyl alcohol administration for cancer treatment |
|---|
- 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 |
|---|
- 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 IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022530 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
482 |
| KEGG Compound ID |
C00612 |
| BioCyc ID |
CPD-568 |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB01276 |
| Metagene Link |
HMDB01276 |
| METLIN ID |
3323 |
| PubChem Compound |
496 |
| PDB ID |
Not Available |
| ChEBI ID |
17927 |
| References |
|---|
| Synthesis Reference |
Lurdes 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 |
- Hrushesky WJ, Merdink J, Abdel-Monem MM: Circadian rhythmicity of polyamine urinary excretion. Cancer Res. 1983 Aug;43(8):3944-7.
Pubmed: 6861156
- 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
- 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
- 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
|
