You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
| Identification |
|---|
| YMDB ID | YMDB00232 |
|---|
| Name | Spermidine |
|---|
| Species | Saccharomyces cerevisiae |
|---|
| Strain | Baker's yeast |
|---|
| Description | Spermidine, also known as SPD, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Spermidine is a very strong basic compound (based on its pKa). Spermidine exists in all living species, ranging from bacteria to humans. Within yeast, spermidine participates in a number of enzymatic reactions. In particular, 3-aminopropanal and spermidine can be biosynthesized from spermine through the action of the enzyme polyamine oxidase. In addition, 5'-methylthioadenosine and spermidine can be biosynthesized from putrescine and S-adenosylmethioninamine through the action of the enzyme spermidine synthase. In yeast, spermidine is involved in the metabolic pathway called the beta-alanine metabolism pathway. Spermidine is a potentially toxic compound. |
|---|
| Structure | |
|---|
| Synonyms | - 1,5,10-Triazadecane
- 1,8-Diamino-4-azaoctane
- 4-Azaoctamethylenediamine
- 4-Azaoctane-1,8-diamine
- Aminopropylbutandiamine
- N-(3-Aminopropyl)-1,4-butane-diamine
- N-(3-Aminopropyl)-1,4-butanediamine
- N-(3-Aminopropyl)-1,4-diamino-butane
- N-(3-Aminopropyl)-1,4-diaminobutane
- N-(3-Aminopropyl)-4-aminobutylamine
- N-(4-Aminobutyl)-1,3-diaminopropane
- N-(gamma-aminopropyl)tetramethylenediamine
- SPD
- Spermidin
- Spermidine
|
|---|
| CAS number | 124-20-9 |
|---|
| Weight | Average: 145.2459
Monoisotopic: 145.157897623 |
|---|
| InChI Key | ATHGHQPFGPMSJY-UHFFFAOYSA-N |
|---|
| InChI | InChI=1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2 |
|---|
| IUPAC Name | (4-aminobutyl)(3-aminopropyl)amine |
|---|
| Traditional IUPAC Name | spermidine |
|---|
| Chemical Formula | C7H19N3 |
|---|
| SMILES | [H]N([H])C([H])([H])C([H])([H])C([H])([H])N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] |
|---|
| Chemical Taxonomy |
|---|
| Description | belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Organic nitrogen compounds |
|---|
| Class | Organonitrogen compounds |
|---|
| Sub Class | Amines |
|---|
| Direct Parent | Dialkylamines |
|---|
| Alternative Parents | |
|---|
| Substituents | - Secondary aliphatic amine
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Primary aliphatic amine
- Aliphatic acyclic compound
|
|---|
| Molecular Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | |
|---|
| Physical Properties |
|---|
| State | Liquid |
|---|
| Charge | 0 |
|---|
| Melting point | < 25 °C |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Water Solubility | Not Available | PhysProp | | LogP | Not Available | PhysProp |
|
|---|
| Predicted Properties | |
|---|
| Biological Properties |
|---|
| Cellular Locations | |
|---|
| Organoleptic Properties | Not Available |
|---|
| SMPDB Pathways | |
|---|
| KEGG Pathways | |
|---|
| SMPDB Reactions | |
|---|
| KEGG Reactions | |
|---|
| Concentrations |
|---|
| Intracellular Concentrations | | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
|---|
| 1339 ± 67 µM | YEB media with 0.5 mM glucose | aerobic | Baker's yeast | Experimentally Determined
Not Available | | Conversion Details Here |
|
|---|
| Extracellular Concentrations | Not Available |
|---|
| Spectra |
|---|
| Spectra |
|---|
| References |
|---|
| References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Pirkov, I., Norbeck, J., Gustafsson, L., Albers, E. (2008). "A complete inventory of all enzymes in the eukaryotic methionine salvage pathway." FEBS J 275:4111-4120.18625006
- Uemura, T., Kashiwagi, K., Igarashi, K. (2007). "Polyamine uptake by DUR3 and SAM3 in Saccharomyces cerevisiae." J Biol Chem 282:7733-7741.17218313
|
|---|
| Synthesis Reference: | Bergeron, Raymond J., Jr. Preparation and formulation spermidine analogues for pharmaceutical use as tumor growth inhibitors. U.S. (2001), 31 pp. |
|---|
| External Links: | |
|---|
