| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:43:09 UTC |
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| Update Date | 2020-06-04 20:46:15 UTC |
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| BMDB ID | BMDB0001256 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Spermine |
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| Description | Spermine, also known as gerontine or musculamine, 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. Spermine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Spermine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Spermine exists in all living species, ranging from bacteria to humans. 5'-Methylthioadenosine and spermine can be biosynthesized from S-adenosylmethioninamine and spermidine through the action of the enzyme spermine synthase. In cattle, spermine is involved in the metabolic pathway called spermidine and spermine biosynthesis pathway. Spermine is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 4,9-Diaza-1,12-dodecanediamine | ChEBI | | 4,9-Diazadodecane-1,12-diamine | ChEBI | | N,N'-bis(3-aminopropyl)-1,4-butanediamine | ChEBI | | 1,5,10,14-Tetraazatetradecane | HMDB | | 4,9-Diazadodecamethylenediamine | HMDB | | Diaminopropyl-tetramethylenediamine | HMDB | | Diaminopropyltetramethylenediamine | HMDB | | Gerontine | HMDB | | Musculamine | HMDB | | N,N'-bis(3-aminopropyl)-1,4-tetramethylenediamine | HMDB | | N,N'-bis(3-aminopropyl)butane-1,4-diamine | HMDB | | N1,N4-Bis(3-aminopropyl)-1,4-butanediamine | HMDB | | Neuridine | HMDB | | Spermin | HMDB | | Spermine dihydrate | HMDB | | Spermine puriss | HMDB | | SPM | HMDB |
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| Chemical Formula | C10H26N4 |
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| Average Molecular Weight | 202.3402 |
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| Monoisotopic Molecular Weight | 202.215746852 |
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| IUPAC Name | (3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine |
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| Traditional Name | spermine |
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| CAS Registry Number | 71-44-3 |
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| SMILES | NCCCNCCCCNCCCN |
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| InChI Identifier | InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2 |
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| InChI Key | PFNFFQXMRSDOHW-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 | 29 °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
- Milk
- Neuron
- Pancreas
- 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 +/- 0.2 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 | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 0.2 +/- 0.1 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1.0700 - 7.560 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3.2 uM | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Pancreas | 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 | 3 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 0.11 +/- 0.03 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Expected but not Quantified | Not Quantified | 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 | HMDB0001256 |
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| DrugBank ID | DB00127 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB003225 |
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| KNApSAcK ID | C00001432 |
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| Chemspider ID | 1072 |
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| KEGG Compound ID | C00750 |
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| BioCyc ID | SPERMINE |
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| BiGG ID | 35875 |
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| Wikipedia Link | Spermine |
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| METLIN ID | 255 |
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| PubChem Compound | 1103 |
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| PDB ID | Not Available |
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| ChEBI ID | 15746 |
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| References |
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| Synthesis Reference | Wrede, Fritz; Strack, Erich; Hettche, Otto. Spermine. VII. Z. physiol. Chem. (1928), 173 61-8. |
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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 ]
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