Canmetcon
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Identification
YMDB IDYMDB00231
NameSpermine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionSpermine is a polyamine formed from spermidine. Polyamines (e.g. spermidine, putrescine, spermine) are a ubiquitous group of compounds involved in many biological processes, including binding to nucleic acids, stabilizing membranes, and stimulating several enzymes. [Biocyc POLYAMINSYN3-PWY]
Structure
Thumb
Synonyms
  • 1,5,10,14-Tetraazatetradecane
  • 4,9-Diaza-1,12-dodecanediamine
  • 4,9-Diazadodecamethylenediamine
  • 4,9-Diazadodecane-1,12-diamine
  • diaminopropyl-tetramethylenediamine
  • Diaminopropyltetramethylenediamine
  • Gerontine
  • Musculamine
  • N,N'-bis(3-aminopropyl)-1,4-Butanediamine
  • N,N'-Bis(3-aminopropyl)-1,4-tetramethylenediamine
  • N,N'-Bis(3-aminopropyl)butane-1,4-diamine
  • N1,N4-bis(3-aminopropyl)-1,4-butanediamine
  • Neuridine
  • Spermin
  • Spermine
  • Spermine dihydrate
  • Spermine puriss
  • SPM
CAS number71-44-3
WeightAverage: 202.3402
Monoisotopic: 202.215746852
InChI KeyPFNFFQXMRSDOHW-UHFFFAOYSA-N
InChIInChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
IUPAC Name(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine
Traditional IUPAC Namespermine
Chemical FormulaC10H26N4
SMILES[H]N([H])C([H])([H])C([H])([H])C([H])([H])N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H]
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentDialkylamines
Alternative Parents
Substituents
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point29 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.19 g/LALOGPS
logP-0.66ALOGPS
logP-1.5ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)11.1ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area76.1 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity62.56 m³·mol⁻¹ChemAxon
Polarizability26.69 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Glutathione metabolismPW002395 ThumbThumb?image type=greyscaleThumb?image type=simple
beta-Alanine metabolismPW002381 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
Glutathione metabolismec00480 Map00480
beta-Alanine metabolismec00410 Map00410
SMPDB Reactions
Spermine + water + oxygenHydrogen peroxide + 3-Aminopropionaldehyde + Spermidine
Spermidine + S-Adenosylmethioninaminehydron + 5'-Methylthioadenosine + Spermine
KEGG Reactions
Spermine + Acetyl-CoAN1-Acetylspermine + hydron + Coenzyme A
Spermine + water + oxygenSpermidine + 3-Aminopropionaldehyde + Hydrogen peroxide
Spermidine + S-AdenosylmethioninamineSpermine + hydron + 5'-Methylthioadenosine
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
223 ± 11 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Pirkov, I., Norbeck, J., Gustafsson, L., Albers, E. (2008). "A complete inventory of all enzymes in the eukaryotic methionine salvage pathway." FEBS J 275:4111-4120.18625006
  • Tomitori, H., Kashiwagi, K., Sakata, K., Kakinuma, Y., Igarashi, K. (1999). "Identification of a gene for a polyamine transport protein in yeast." J Biol Chem 274:3265-3267.9920864
Synthesis Reference:Wrede, Fritz; Strack, Erich; Hettche, Otto. Spermine. VII. Z. physiol. Chem. (1928), 173 61-8.
External Links:
ResourceLink
CHEBI ID15746
HMDB IDHMDB01256
Pubchem Compound ID1103
Kegg IDC00750
ChemSpider ID1072
FOODB IDFDB003225
WikipediaSpermine
BioCyc IDSPERMINE

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Involved in the production of beta-alanine, a precursor of pantothenic acid. Multicopy suppressor of fenpropimorph resistance
Gene Name:
FMS1
Uniprot ID:
P50264
Molecular weight:
57805.10156
Reactions
Spermine + O(2) + H(2)O → spermidine + 3-aminopropanal + H(2)O(2).
Spermidine + O(2) + H(2)O → putrescine + 3-aminopropanal + H(2)O(2).
N(1)-acetylspermine + O(2) + H(2)O → spermidine + 3-acetamidopropanal + H(2)O(2).
N(1)-acetylspermidine + O(2) + H(2)O → putrescine + 3-acetamidopropanal + H(2)O(2).
N(8)-acetylspermidine + O(2) + H(2)O → 4-acetamidobutanal + trimethylenediamine + H(2)O(2).
General function:
Involved in catalytic activity
Specific function:
S-adenosylmethioninamine + spermidine = 5'- methylthioadenosine + spermine
Gene Name:
SPE4
Uniprot ID:
Q12455
Molecular weight:
34090.5
Reactions
S-adenosylmethioninamine + spermidine → 5'-methylthioadenosine + spermine.

Transporters

General function:
Involved in transmembrane transport
Specific function:
Cell membrane polyamine/proton antiporter, involved in the detoxification of excess polyamines in the cytoplasm. Catalyzes polyamine uptake at alkaline pH and excretion at acidic pH. Recognizes spermidine, spermine and putrescine, the polyamine analogs methylglyoxal bis(guanylhydrazone) (MGBG) and paraquat, the antimalarial drug quinidine, and cycloheximide. Confers resistance to the non-steroidal anti-inflammatory drug indomethacin
Gene Name:
TPO1
Uniprot ID:
Q07824
Molecular weight:
64271.60156