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

Escherichia coli K-12 substr. MG1655 Compound: spermidine

Synonyms: N-(3-aminopropyl)butane-1,4-diamine

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

Chemical Formula: C7H22N3

Molecular Weight: 148.27 Daltons

Monoisotopic Molecular Weight: 145.1578976255 Daltons

SMILES: C([N+])CC[N+]CCCC[N+]

InChI: InChI=1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2/p+3

InChIKey: InChIKey=ATHGHQPFGPMSJY-UHFFFAOYSA-Q

Unification Links: CAS:124-20-9 , ChEBI:57834 , ChemSpider:5360248 , HMDB:HMDB01257 , IAF1260:34593 , KEGG:C00315 , MetaboLights:MTBLC57834 , PubChem:6992097

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 4.79

Reactions known to consume the compound:

glutathionylspermidine biosynthesis :
spermidine + glutathione + ATP → glutathionylspermidine + ADP + phosphate + H+

Not in pathways:
acetyl-CoA + spermidineN1-acetylspermidine + coenzyme A + H+


an aliphatic amine[periplasmic space] + H2O[periplasmic space] + oxygen[periplasmic space] → an aldehyde[periplasmic space] + ammonium[periplasmic space] + hydrogen peroxide[periplasmic space]

Reactions known to produce the compound:

spermidine biosynthesis I :
putrescine + S-adenosyl 3-(methylthio)propylamine → spermidine + S-methyl-5'-thioadenosine + H+

Not in pathways:
glutathionylspermidine + H2O → glutathione + spermidine

Reactions known to both consume and produce the compound:

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

In Reactions of unknown directionality:

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

In Transport reactions:
spermidine[cytosol] + H+[periplasmic space]spermidine[periplasmic space] + H+[cytosol] ,
ATP + spermidine[periplasmic space] + H2O → ADP + spermidine[cytosol] + phosphate + H+

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

Activator (Mechanism unknown) of: acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase [Vallari82]

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

Inhibitor (Competitive) of: ornithine decarboxylase [Applebaum77] , arginine decarboxylase, degradative [Blethen68]

Inhibitor (Mechanism unknown) of: spermidine synthase [Bowman73, Comment 1] , arginine decarboxylase, biosynthetic [Wu73, Comment 2] , adenosylmethionine decarboxylase [Tabor85, Kashiwagi88] , dihydrofolate reductase [Baccanari75] , lysine decarboxylase [Wertheimer83]

Activates: AtoS[inner membrane] + ATP → AtoS-P[inner membrane] + ADP

Regulated Transcription Units (1 total): ?

Notes:


References

Applebaum77: Applebaum DM, Dunlap JC, Morris DR (1977). "Comparison of the biosynthetic and biodegradative ornithine decarboxylases of Escherichia coli." Biochemistry 1977;16(8);1580-4. PMID: 15587

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

Blethen68: Blethen SL, Boeker EA, Snell EE (1968). "Argenine decarboxylase from Escherichia coli. I. Purification and specificity for substrates and coenzyme." J Biol Chem 1968;243(8);1671-7. PMID: 4870599

Bowman73: Bowman WH, Tabor CW, Tabor H (1973). "Spermidine biosynthesis. Purification and properties of propylamine transferase from Escherichia coli." J Biol Chem 1973;248(7);2480-6. PMID: 4572733

Kashiwagi88: Kashiwagi K, Igarashi K (1988). "Adjustment of polyamine contents in Escherichia coli." J Bacteriol 170(7);3131-5. PMID: 3290196

Tabor83a: Tabor CW, Tabor H (1983). "Putrescine aminopropyltransferase (Escherichia coli)." Methods Enzymol 1983;94;265-70. PMID: 6312268

Tabor85: Tabor CW, Tabor H (1985). "Polyamines in microorganisms." Microbiol Rev 1985;49(1);81-99. PMID: 3157043

Vallari82: Vallari DS, Rock CO (1982). "Role of spermidine in the activity of sn-glycerol-3-phosphate acyltransferase from Escherichia coli." Arch Biochem Biophys 1982;218(2);402-8. PMID: 6760815

Wertheimer83: Wertheimer SJ, Leifer Z (1983). "Putrescine and spermidine sensitivity of lysine decarboxylase in Escherichia coli: evidence for a constitutive enzyme and its mode of regulation." Biochem Biophys Res Commun 114(2);882-8. PMID: 6349639

Wu73: Wu WH, Morris DR (1973). "Biosynthetic arginine decarboxylase from Escherichia coli. Purification and properties." J Biol Chem 1973;248(5);1687-95. PMID: 4571773


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 18.5 on Wed Dec 17, 2014, BIOCYC13A.