MetaCyc Compound: spermine

Systematic Name: N,N'-Bis(3-aminopropyl)-1,4-butane-diamine

Synonyms: gerontine, musculamine, neuridine, diaminopropyl-tetramethylenediamine

Superclasses: an aminean aliphatic aminean aliphatic diaminean aliphatic alpha,omega-diamine

The history of spermine biochemistry goes back more than 300 years. When Antoni van Leeuwenhoek looked at human semen through the lenses of his microscope in 1678, he noted the formation of crystals in aging sperm. More than 200 years later, the basic component of these phosphate crystals was named spermine, after the source [Galston90].

Chemical Formula: C10H30N4

Molecular Weight: 206.37 Daltons

Monoisotopic Molecular Weight: 206.2470469838 Daltons

spermine compound structure


InChI: InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2/p+4


Unification Links: CAS:71-44-3, ChEBI:45725, ChemSpider:394003, DrugBank:DB02564, HMDB:HMDB01256, KEGG:C00750, MetaboLights:MTBLC45725, PubChem:446718

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 318.74066Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

β-alanine biosynthesis IV , spermine and spermidine degradation III :
spermine + oxygen + H2O → spermidine + 3-aminopropanal + hydrogen peroxide

spermine and spermidine degradation I :
acetyl-CoA + spermineN1-acetylspermine + coenzyme A + H+
spermine + oxygen + H2O → spermidine + 3-aminopropanal + hydrogen peroxide

spermine and spermidine degradation II :
spermine + oxygen + H2O → 1-(3-aminopropyl)-4-aminobutanal + propane-1,3-diamine + hydrogen peroxide

Not in pathways:
an aliphatic amine + H2O + oxygen → an aldehyde + ammonium + hydrogen peroxide

Not in pathways:
an amine + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + a methylated amine

Reactions known to produce the compound:

spermine biosynthesis , superpathway of polyamine biosynthesis II :
spermidine + S-adenosyl 3-(methylthio)propylamine → spermine + S-methyl-5'-thioadenosine + H+

Reactions known to both consume and produce the compound:

Not in pathways:
an aliphatic α,ω-diamine + 2-oxoglutarate ↔ L-glutamate + an aliphatic ω-aminoaldehyde

In Reactions of unknown directionality:

Not in pathways:
acetyl-CoA + an aliphatic α,ω-diamine = an aliphatic N-acetyl-diamine + coenzyme A + H+

Not in pathways:
an aliphatic amine + an oxidized cytochrome c550 + H2O = an aldehyde + ammonium + a reduced cytochrome c550

Not in pathways:
3'-phosphoadenylyl-sulfate + an amine = adenosine 3',5'-bisphosphate + a sulfamate

Enzymes activated by spermine, sorted by the type of activation, are:

Activator (Mechanism unknown) of: phosphatidylinositol-4-phosphate 5-kinase [Loijens96]

Enzymes inhibited by spermine, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: spermine synthase [Raina83] Inhibitor (Mechanism unknown) of: dihydrofolate reductase [Baccanari75]

This compound has been characterized as an alternative substrate of the following enzymes: spermidine acetyltransferase, polyamine aminotransferase


Baccanari75: Baccanari D, Phillips A, Smith S, Sinski D, Burchall J (1975). "Purification and properties of Escherichia coli dihydrofolate reductase." Biochemistry 1975;14(24);5267-73. PMID: 46

Galston90: Galston AW, Sawhney RK (1990). "Polyamines in plant physiology." Plant Physiol 94(2);406-10. PMID: 11537482

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Loijens96: Loijens JC, Boronenkov IV, Parker GJ, Anderson RA (1996). "The phosphatidylinositol 4-phosphate 5-kinase family." Adv Enzyme Regul 36;115-40. PMID: 8869744

Raina83: Raina A, Pajula RL, Eloranta T (1983). "Purification of spermidine aminopropyltransferase (spermine synthase) from bovine brain." Methods Enzymol 94;276-9. PMID: 6621388

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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