Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:15:27 UTC |
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Update date | 2019-11-26 03:21:04 UTC |
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Primary ID | FDB022530 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | N1-Acetylspermidine |
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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) [HMDB]. N1-Acetylspermidine is found in many foods, some of which are anise, kohlrabi, lime, and borage. |
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CAS Number | 14278-49-0 |
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Structure | |
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Synonyms | Synonym | Source |
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1-N-Acetylspermidine | ChEBI | An N-acetylspermidine | HMDB | N(1)-Acetylspermidine | HMDB | N-(3-((4-Aminobutyl)amino)propyl)-acetamide | HMDB | N-(3-((4-Aminobutyl)amino)propyl)acetamide | HMDB | N-Acetylspermidine | HMDB | N1-Acetylspermidine | ChEBI | an N-acetylspermidine | hmdb | N-(3-((4-aminobutyl)amino)propyl)-Acetamide | hmdb |
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Predicted Properties | |
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Chemical Formula | C9H21N3O |
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IUPAC name | N-{3-[(4-aminobutyl)amino]propyl}acetamide |
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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) |
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InChI Key | MQTAVJHICJWXBR-UHFFFAOYSA-N |
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Isomeric SMILES | CC(=O)NCCCNCCCCN |
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Average Molecular Weight | 187.2825 |
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Monoisotopic Molecular Weight | 187.168462309 |
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Classification |
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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). |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboximidic acids and derivatives |
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Sub Class | Carboximidic acids |
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Direct Parent | Carboximidic acids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | N1-Acetylspermidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00ec-9300000000-435442e25431afc9ca94 | Spectrum | Predicted GC-MS | N1-Acetylspermidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00g1-1900000000-25a42a25b21ff785892b | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05dj-6900000000-12de75772a08ca08852a | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fu-9200000000-2dfa5d648a84baff3e54 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-1900000000-90283b76b9478101a593 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052o-5900000000-4cac7a34f5b572449747 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9000000000-46e81717ccd7a43b7c55 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0079-3900000000-7dcca0a83898d18d48ff | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ab9-9300000000-db42164e7ae02cc3565e | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05gi-9000000000-b73b9a6524aaa490eb70 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-b573184691a2508c0c96 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4r-9700000000-683029d89d5350729ba4 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9000000000-236e795417fce314ee2b | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 482 |
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ChEMBL ID | CHEMBL176800 |
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KEGG Compound ID | C00612 |
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Pubchem Compound ID | 496 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17927 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB01276 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Diamine acetyltransferase 2 | SAT2 | Q96F10 | Diamine acetyltransferase 1 | SAT1 | P21673 |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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