CHEBI:15746 - spermine

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ChEBI Name spermine
ChEBI ID CHEBI:15746
Definition A polyazaalkane that is tetradecane in which the carbons at positions 1, 5, 10 and 14 are replaced by nitrogens. Spermine has broad actions on cellular metabolism.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:15098, CHEBI:45583, CHEBI:9219, CHEBI:26734
Supplier Information No supplier information found for this compound.
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Oxygen is a chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and a potent oxidizing agent that readily forms oxides with most elements as well as with other compounds. Oxygen is the most abundant element in Earth's crust, and the third-most abundant element in the universe after hydrogen and helium. At standard temperature and pressure, two oxygen atoms will bind covalently to form dioxygen, a colorless and odorless diatomic gas with the chemical formula O2. Dioxygen gas currently constitutes approximately 20.95% molar fraction of the Earth's atmosphere, though this has changed considerably over long periods of time in Earth's history. Oxygen makes up almost half of the Earth's crust in the form of various oxides such as water, carbon dioxide, iron oxides and silicates. All eukaryotic organisms, including plants, animals, fungi, algae and most protists, need oxygen for cellular respiration, which extracts chemical energy by the reaction of oxygen with organic molecules derived from food and releases carbon dioxide as a waste product. In aquatic animals, dissolved oxygen in water is absorbed by specialized respiratory organs called gills, through the skin or via the gut; in terrestrial animals such as tetrapods, oxygen in air is actively taken into the body via specialized organs known as lungs, where gas exchange takes place to diffuse oxygen into the blood and carbon dioxide out, and the body's circulatory system then transports the oxygen to other tissues where cellular respiration takes place. However in insects, the most successful and biodiverse terrestrial clade, oxygen is directly conducted to the internal tissues via a deep network of airways. Many major classes of organic molecules in living organisms contain oxygen atoms, such as proteins, nucleic acids, carbohydrates and fats, as do the major constituent inorganic compounds of animal shells, teeth, and bone. Most of the mass of living organisms is oxygen as a component of water, the major constituent of lifeforms. Oxygen in Earth's atmosphere is produced by biotic photosynthesis, in which photon energy in sunlight is captured by chlorophyll to split water molecules and then react with carbon dioxide to produce carbohydrates and oxygen is released as a byproduct. Oxygen is too chemically reactive to remain a free element in air without being continuously replenished by the photosynthetic activities of autotrophs such as cyanobacteria, chloroplast-bearing algae and plants. A much rarer triatomic allotrope of oxygen, ozone (O3), strongly absorbs the UVB and UVC wavelengths and forms a protective ozone layer at the lower stratosphere, which shields the biosphere from ionizing ultraviolet radiation. However, ozone present at the surface is a corrosive byproduct of smog and thus an air pollutant. Oxygen was isolated by Michael Sendivogius before 1604, but it is commonly believed that the element was discovered independently by Carl Wilhelm Scheele, in Uppsala, in 1773 or earlier, and Joseph Priestley in Wiltshire, in 1774. Priority is often given for Priestley because his work was published first. Priestley, however, called oxygen "dephlogisticated air", and did not recognize it as a chemical element. The name oxygen was coined in 1777 by Antoine Lavoisier, who first recognized oxygen as a chemical element and correctly characterized the role it plays in combustion. Common industrial uses of oxygen include production of steel, plastics and textiles, brazing, welding and cutting of steels and other metals, rocket propellant, oxygen therapy, and life support systems in aircraft, submarines, spaceflight and diving.
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Formula C10H26N4
Net Charge 0
Average Mass 202.34040
Monoisotopic Mass 202.21575
InChI InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
InChIKey PFNFFQXMRSDOHW-UHFFFAOYSA-N
SMILES NCCCNCCCCNCCCN
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Daphnia magna (NCBI:txid35525) See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): fundamental metabolite
Any metabolite produced by all living cells.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
Application(s): immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
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ChEBI Ontology
Outgoing spermine (CHEBI:15746) has role antioxidant (CHEBI:22586)
spermine (CHEBI:15746) has role fundamental metabolite (CHEBI:78675)
spermine (CHEBI:15746) has role immunosuppressive agent (CHEBI:35705)
spermine (CHEBI:15746) is a polyazaalkane (CHEBI:39474)
spermine (CHEBI:15746) is a tetramine (CHEBI:39166)
spermine (CHEBI:15746) is conjugate base of spermine(4+) (CHEBI:45725)
Incoming N4-aminopropylspermine (CHEBI:83554) has functional parent spermine (CHEBI:15746)
substituted spermine (CHEBI:26735) has functional parent spermine (CHEBI:15746)
spermine(4+) (CHEBI:45725) is conjugate acid of spermine (CHEBI:15746)
IUPAC Name
N,N'-bis(3-aminopropyl)butane-1,4-diamine
Synonyms Sources
4,9-diaza-1,12-dodecanediamine NIST Chemistry WebBook
4,9-diazadodecane-1,12-diamine NIST Chemistry WebBook
N,N'-Bis(3-aminopropyl)-1,4-butanediamine KEGG COMPOUND
Spermine KEGG COMPOUND
SPERMINE PDBeChem
Manual Xrefs Databases
C00001432 KNApSAcK
C00750 KEGG COMPOUND
DB00127 DrugBank
HMDB0001256 HMDB
Spermine Wikipedia
SPERMINE MetaCyc
SPM PDBeChem
View more database links
Registry Numbers Types Sources
1750791 Reaxys Registry Number Reaxys
454653 Gmelin Registry Number Gmelin
71-44-3 CAS Registry Number KEGG COMPOUND
71-44-3 CAS Registry Number ChemIDplus
71-44-3 CAS Registry Number NIST Chemistry WebBook
Citations
Last Modified
27 January 2016