| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:43:10 UTC |
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| Update Date | 2020-06-04 20:47:30 UTC |
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| BMDB ID | BMDB0001257 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Spermidine |
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| 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 exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Spermidine exists in all living species, ranging from bacteria to humans. Spermidine is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 1,5,10-Triazadecane | ChEBI | | 4-Azaoctamethylenediamine | ChEBI | | 4-Azaoctane-1,8-diamine | ChEBI | | N-(3-Aminopropyl)-1,4-butane-diamine | ChEBI | | Spermidin | ChEBI | | 1,8-Diamino-4-azaoctane | HMDB | | Aminopropylbutandiamine | HMDB | | N-(3-Aminopropyl)-1,4-butanediamine | HMDB | | N-(3-Aminopropyl)-1,4-diamino-butane | HMDB | | N-(3-Aminopropyl)-1,4-diaminobutane | HMDB | | N-(3-Aminopropyl)-4-aminobutylamine | HMDB | | N-(4-Aminobutyl)-1,3-diaminopropane | HMDB | | N-(gamma-Aminopropyl)tetramethylenediamine | HMDB | | SPD | HMDB |
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| Chemical Formula | C7H19N3 |
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| Average Molecular Weight | 145.2459 |
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| Monoisotopic Molecular Weight | 145.157897623 |
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| IUPAC Name | (4-aminobutyl)(3-aminopropyl)amine |
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| Traditional Name | spermidine |
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| CAS Registry Number | 124-20-9 |
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| SMILES | NCCCCNCCCN |
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| InChI Identifier | InChI=1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2 |
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| InChI Key | ATHGHQPFGPMSJY-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic nitrogen compounds |
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| Class | Organonitrogen compounds |
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| Sub Class | Amines |
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| Direct Parent | Dialkylamines |
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| Alternative Parents | |
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| Substituents | - Secondary aliphatic amine
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Primary aliphatic 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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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | < 25 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | |
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| Biospecimen Locations | - Blood
- Brain
- Epidermis
- Erythrocyte
- Fibroblasts
- Intestine
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Neuron
- Placenta
- Platelet
- Prostate Tissue
- Ruminal Fluid
- Semimembranosus Muscle
- Testis
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 0.2 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Erythrocyte | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 0.09 +/- 0.03 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 13.2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2.200 - 4.400 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.88 +/- 0.02 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.89 +/- 0.02 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.84 +/- 0.02 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.70 +/- 0.03 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Platelet | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 37 +/- 22 uM | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 0.11 +/- 0.04 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 0.4 +/- 0.2 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| HMDB ID | HMDB0001257 |
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| DrugBank ID | DB03566 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB012039 |
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| KNApSAcK ID | C00001431 |
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| Chemspider ID | 1071 |
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| KEGG Compound ID | C00315 |
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| BioCyc ID | SPERMIDINE |
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| BiGG ID | 34593 |
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| Wikipedia Link | Spermidine |
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| METLIN ID | 254 |
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| PubChem Compound | 1102 |
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| PDB ID | Not Available |
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| ChEBI ID | 16610 |
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| References |
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| Synthesis Reference | Bergeron, Raymond J., Jr. Preparation and formulation spermidine analogues for pharmaceutical use as tumor growth inhibitors. U.S. (2001), 31 pp. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Motyl T, Ploszaj T, Wojtasik A, Kukulska W, Podgurniak M: Polyamines in cow's and sow's milk. Comp Biochem Physiol B Biochem Mol Biol. 1995 Jul;111(3):427-33. [PubMed:7613766 ]
- Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
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