| Record Information |
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| Version | 1.0 |
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| Creation date | 2018-05-02 12:45:58 UTC |
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| Update date | 2018-05-04 14:15:36 UTC |
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| FoodComEx ID | PC001211 |
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| FoodDB Record | FDB022530 |
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| Chemical Information |
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| 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 | hmdb | | an N-acetylspermidine | hmdb | | N-(3-((4-aminobutyl)amino)propyl)-Acetamide | hmdb | | N-(3-((4-Aminobutyl)amino)propyl)acetamide | hmdb | | N-Acetylspermidine | hmdb | | N(1)-Acetylspermidine | hmdb | | N1-Acetylspermidine | hmdb |
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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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| Chemical Taxonomy |
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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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| Physico-Chemical Properties - Experimental |
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| Property | Value | Reference |
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| Experimental logP | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Melting Point | Not Available | |
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| Foods of Origin |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Production Data |
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| Production Method | commercial |
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| Production Method Reference | Not Available |
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| Production Method Reference File | Not Available |
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| Quantity Available | 1 to 2 mg |
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| Delivery Time | 2 weeks |
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| Storage Form | powder |
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| Storage Conditions | -18°C |
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| Stability | Not Available |
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| Purity | unknown |
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| Spectra |
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| Spectral Data Upon Request | Not Available |
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| Provider Information |
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| Contact Name | Contact Institution | Contact Email |
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| Augustin Scalbert | International Agency for Research on Cancer (IARC), Biomarkers Group, 150 cours Albert Thomas, Lyon, FR, 69372 | scalberta@iarc.fr |
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| Commercial Vendors |
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| Not Available |
