Spermine
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Basic Info
| Common Name | Spermine(F05250) |
| 2D Structure | |
| Description | Spermine is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. |
| FRCD ID | F05250 |
| CAS Number | 71-44-3 |
| PubChem CID | 1103 |
| Formula | C10H26N4 |
| IUPAC Name | N,N'-bis(3-aminopropyl)butane-1,4-diamine |
| InChI Key | PFNFFQXMRSDOHW-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2 |
| Canonical SMILES | C(CCNCCCN)CNCCCN |
| Isomeric SMILES | C(CCNCCCN)CNCCCN |
| Wikipedia | Spermine |
| Synonyms |
Spermin
N,N'-Bis(3-aminopropyl)-1,4-butanediamine
spermine
71-44-3
gerontine
musculamine
neuridine
4,9-Diaza-1,12-dodecanediamine
Diaminopropyltetramethylenediamine
Spermine, puriss
|
| Classifies |
Predicted: Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic nitrogen compounds |
| Class | Organonitrogen compounds |
| Subclass | Amines |
| Intermediate Tree Nodes | Secondary amines |
| Direct Parent | Dialkylamines |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Secondary aliphatic amine - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Primary aliphatic amine - Aliphatic acyclic compound |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 202.346 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 11 |
| Complexity | 86.1 |
| Monoisotopic Mass | 202.216 |
| Exact Mass | 202.216 |
| XLogP | -1.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.6345 |
| Human Intestinal Absorption | HIA+ | 0.9215 |
| Caco-2 Permeability | Caco2+ | 0.7072 |
| P-glycoprotein Substrate | Non-substrate | 0.5094 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9178 |
| Non-inhibitor | 0.6414 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.6066 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.9073 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8863 |
| CYP450 2D6 Substrate | Non-substrate | 0.5607 |
| CYP450 3A4 Substrate | Non-substrate | 0.8262 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8770 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9072 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9502 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9026 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9703 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9386 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7691 |
| Non-inhibitor | 0.7739 | |
| AMES Toxicity | Non AMES toxic | 0.8957 |
| Carcinogens | Non-carcinogens | 0.6436 |
| Fish Toxicity | Low FHMT | 0.7738 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.8896 |
| Honey Bee Toxicity | Low HBT | 0.5977 |
| Biodegradation | Ready biodegradable | 0.5525 |
| Acute Oral Toxicity | III | 0.6931 |
| Carcinogenicity (Three-class) | Non-required | 0.6532 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.4998 | LogS |
| Caco-2 Permeability | 0.7135 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4561 | LD50, mol/kg |
| Fish Toxicity | 2.5364 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.1935 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Detection of biogenic amines in pet food ingredients by RP-HPLC with automated dansyl chloride derivatisation. | J Sep Sci | 2018 Oct 14 | 30318732 |
| Supplementing phytogenic compounds or autolyzed yeast modulates ruminal biogenic amines and plasma metabolome in dry cows experiencing subacute ruminal acidosis. | J Dairy Sci | 2018 Jul 18 | 30031584 |
| Roles of spermine in modulating the antioxidant status and Nrf2 signallingmolecules expression in the thymus and spleen of suckling piglets-new insight. | J Anim Physiol Anim Nutr (Berl) | 2018 Feb | 28503850 |
| Spermine and spermidine are cytotoxic towards intestinal cell cultures, but are they a health hazard at concentrations found in foods? | Food Chem | 2018 Dec 15 | 30100441 |
| Effect of lantibiotic gallidermin against biogenic amine-producing faecalstaphylococci from ostriches and pheasants. | Folia Microbiol (Praha) | 2017 May | 28084600 |
| Determination of biogenic amines in licorice (Glycyrrhiza glabra) by ion-pairextraction and liquid chromatography-tandem mass spectrometry. | J Sci Food Agric | 2017 Mar | 27381870 |
| Comparison of Biogenic Amines and Mycotoxins in Alfalfa and Red Clover Fodder Depending on Additives. | Int J Environ Res Public Health | 2017 Apr 14 | 28420109 |
| Effect of oral polyamine supplementation pre-weaning on piglet growth andintestinal characteristics. | Animal | 2016 Oct | 26997172 |
| Content of biogenic amines in Lemna minor (common duckweed) growing in mediumcontaminated with tetracycline. | Aquat Toxicol | 2016 Nov | 27684602 |
| Selection of Amine-Oxidizing Dairy Lactic Acid Bacteria and Identification of the Enzyme and Gene Involved in the Decrease of Biogenic Amines. | Appl Environ Microbiol | 2016 Dec 1 | 27637883 |
| Technological Factors Affecting Biogenic Amine Content in Foods: A Review. | Front Microbiol | 2016 Aug 12 | 27570519 |
| Studies of levels of biogenic amines in meat samples in relation to the contentof additives. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2016 | 26515667 |
| Nanoparticle strategies for cancer therapeutics: Nucleic acids, polyamines, bovine serum amine oxidase and iron oxide nanoparticles (Review). | Int J Oncol | 2015 Jan | 25333509 |
| Solid state fermentation with lactic acid bacteria to improve the nutritional quality of lupin and soya bean. | J Sci Food Agric | 2015 Apr | 25042749 |
| Metabolomic strategy for the detection of metabolic effects of sperminesupplementation in weaned rats. | J Agric Food Chem | 2014 Sep 10 | 25162370 |
| Resembling breast milk: influence of polyamine-supplemented formula on neonatalBALB/cOlaHsd mouse microbiota. | Br J Nutr | 2014 Mar 28 | 24229796 |
| A co culture approach show that polyamine turnover is affected during inflammation in Atlantic salmon immune and liver cells and that arginine and LPS exerts opposite effects on p38MAPK signaling. | Fish Shellfish Immunol | 2014 Apr | 24565893 |
| Melatonin is formed during winemaking at safe levels of biogenic amines. | Food Chem Toxicol | 2013 Jul | 23531627 |
| Biogenic amines in low- and reduced-fat dry fermented sausages formulated withkonjac gel. | J Agric Food Chem | 2012 Sep 12 | 22857776 |
| Mitochondrial membrane permeabilization upon interaction with lysozyme fibrillation products: role of mitochondrial heterogeneity. | Biochim Biophys Acta | 2012 Sep | 22580229 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
- Gene Name:
- CA1
- Uniprot ID:
- P00915
- Molecular Weight:
- 28870.0 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA12
- Uniprot ID:
- O43570
- Molecular Weight:
- 39450.615 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Spermine:oxygen oxidoreductase (spermidine-forming) activity
- Specific Function:
- Flavoenzyme which catalyzes the oxidation of spermine to spermidine. Can also use N(1)-acetylspermine and spermidine as substrates, with different affinity depending on the isoform (isozyme) and on the experimental conditions. Plays an important role in the regulation of polyamine intracellular concentration and has the potential to act as a determinant of cellular sensitivity to the antitumor polyamine analogs. May contribute to beta-alanine production via aldehyde dehydrogenase conversion of 3-amino-propanal.
- Gene Name:
- SMOX
- Uniprot ID:
- Q9NWM0
- Molecular Weight:
- 61818.76 Da
References
- Binda C, Angelini R, Federico R, Ascenzi P, Mattevi A: Structural bases for inhibitor binding and catalysis in polyamine oxidase. Biochemistry. 2001 Mar 6;40(9):2766-76. [11258887 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate exchange activity of SLC26A6.
- Gene Name:
- CA2
- Uniprot ID:
- P00918
- Molecular Weight:
- 29245.895 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Participates in pH regulation. May be involved in the control of cell proliferation and transformation. Appears to be a novel specific biomarker for a cervical neoplasia.
- Gene Name:
- CA9
- Uniprot ID:
- Q16790
- Molecular Weight:
- 49697.36 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Receptor signaling protein activity
- Specific Function:
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
- Gene Name:
- ADRB1
- Uniprot ID:
- P08588
- Molecular Weight:
- 51322.1 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Metal ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA14
- Uniprot ID:
- Q9ULX7
- Molecular Weight:
- 37667.37 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA3
- Uniprot ID:
- P07451
- Molecular Weight:
- 29557.215 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
- Gene Name:
- CA4
- Uniprot ID:
- P22748
- Molecular Weight:
- 35032.075 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Low activity.
- Gene Name:
- CA5A
- Uniprot ID:
- P35218
- Molecular Weight:
- 34750.21 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA5B
- Uniprot ID:
- Q9Y2D0
- Molecular Weight:
- 36433.43 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Its role in saliva is unknown.
- Gene Name:
- CA6
- Uniprot ID:
- P23280
- Molecular Weight:
- 35366.615 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA7
- Uniprot ID:
- P43166
- Molecular Weight:
- 29658.235 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Phosphatidylinositol phospholipase c activity
- Specific Function:
- Senses changes in the extracellular concentration of calcium ions. The activity of this receptor is mediated by a G-protein that activates a phosphatidylinositol-calcium second messenger system.
- Gene Name:
- CASR
- Uniprot ID:
- P41180
- Molecular Weight:
- 120672.385 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Superoxide-generating nadph oxidase activity
- Specific Function:
- Constitutive NADPH oxidase which generates superoxide intracellularly upon formation of a complex with CYBA/p22phox. Regulates signaling cascades probably through phosphatases inhibition. May function as an oxygen sensor regulating the KCNK3/TASK-1 potassium channel and HIF1A activity. May regulate insulin signaling cascade. May play a role in apoptosis, bone resorption and lipolysaccharide-mediated activation of NFKB. May produce superoxide in the nucleus and play a role in regulating gene expression upon cell stimulation. Isoform 3 is not functional. Isoform 5 and isoform 6 display reduced activity.Isoform 4: Involved in redox signaling in vascular cells. Constitutively and NADPH-dependently generates reactive oxygen species (ROS). Modulates the nuclear activation of ERK1/2 and the ELK1 transcription factor, and is capable of inducing nuclear DNA damage. Displays an increased activity relative to isoform 1.
- Gene Name:
- NOX4
- Uniprot ID:
- Q9NPH5
- Molecular Weight:
- 66930.995 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
- Gene Name:
- SLC22A8
- Uniprot ID:
- Q8TCC7
- Molecular Weight:
- 59855.585 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Spermine synthase activity
- Specific Function:
- Catalyzes the production of spermine from spermidine and decarboxylated S-adenosylmethionine (dcSAM).
- Gene Name:
- SMS
- Uniprot ID:
- P52788
- Molecular Weight:
- 41267.855 Da
References
- Lopatin AN, Shantz LM, Mackintosh CA, Nichols CG, Pegg AE: Modulation of potassium channels in the hearts of transgenic and mutant mice with altered polyamine biosynthesis. J Mol Cell Cardiol. 2000 Nov;32(11):2007-24. [11040105 ]
- General Function:
- Protein homodimerization activity
- Specific Function:
- Key enzyme of polyamine biosynthesis that converts ornithine into putrescine, which is the precursor for the polyamines, spermidine and spermine.
- Gene Name:
- ODC1
- Uniprot ID:
- P11926
- Molecular Weight:
- 51147.73 Da
References
- Korhonen VP, Niiranen K, Halmekyto M, Pietila M, Diegelman P, Parkkinen JJ, Eloranta T, Porter CW, Alhonen L, Janne J: Spermine deficiency resulting from targeted disruption of the spermine synthase gene in embryonic stem cells leads to enhanced sensitivity to antiproliferative drugs. Mol Pharmacol. 2001 Feb;59(2):231-8. [11160858 ]
- General Function:
- Protein homodimerization activity
- Specific Function:
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
- Gene Name:
- ADRB2
- Uniprot ID:
- P07550
- Molecular Weight:
- 46458.32 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Vitamin d binding
- Specific Function:
- May have weak glycosidase activity towards glucuronylated steroids. However, it lacks essential active site Glu residues at positions 239 and 872, suggesting it may be inactive as a glycosidase in vivo. May be involved in the regulation of calcium and phosphorus homeostasis by inhibiting the synthesis of active vitamin D (By similarity). Essential factor for the specific interaction between FGF23 and FGFR1 (By similarity).The Klotho peptide generated by cleavage of the membrane-bound isoform may be an anti-aging circulating hormone which would extend life span by inhibiting insulin/IGF1 signaling.
- Gene Name:
- KL
- Uniprot ID:
- Q9UEF7
- Molecular Weight:
- 116179.815 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]