Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

MetaCyc Compound: spermine

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

Synonyms: gerontine, musculamine, neuridine, diaminopropyl-tetramethylenediamine

Superclasses: an amine an aliphatic amine an aliphatic diamine an aliphatic alpha,omega-diamine

Summary:
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: 202.2157468554 Daltons

SMILES: C(CCC[N+]CCC[N+])[N+]CCC[N+]

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

InChIKey: InChIKey=PFNFFQXMRSDOHW-UHFFFAOYSA-R

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

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 318.74066 Inferred 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


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+


an aliphatic amine + an oxidized cytochrome c550 + H2O = an aldehyde + ammonium + a reduced cytochrome c550


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]


References

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Thu Dec 18, 2014, biocyc12.