S-Adenosylmethioninamine (YMDB00130)

Identification
YMDB IDYMDB00130
NameS-Adenosylmethioninamine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionS-Adenosylmethioninamine, also known as decarboxy-adomet or dadomet, belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. S-Adenosylmethioninamine exists in all living species, ranging from bacteria to plants to humans. In yeast, S-adenosylmethioninamine is involved in the metabolic pathway called the beta-alanine metabolism pathway. Based on a literature review a small amount of articles have been published on S-Adenosylmethioninamine.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (5-deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt
  • dAdoMet
  • decarboxylated AdoMet
  • decarboxylated S-adenosylmethionine
  • decarboxylated SAM
  • S-Adenosyl-L-methioninamine
  • S-adenosylmethioninamine
  • (5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium
  • (5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium cation
  • (5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium salt
  • [1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulfonium
  • S-Adenosyl-(5')-3-methylthiopropylamine
  • S-Adenosyl-3-methylthiopropylamine
  • S-Adenosyl 3-(methylthio)propylamine
  • S-Adenosyl 3-(methylsulfanyl)propylamine
  • Decarboxy-adomet
  • (5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulphonium
  • (5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulphonium cation
  • (5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulphonium salt
  • [1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulfonium
  • [1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulphonium
  • [1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulphonium
  • [1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulfonium
  • [1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulphonium
  • S-Adenosyl 3-(methylsulphanyl)propylamine
  • S--Adenosylmethioninamine
  • S-5'-Deoxyadenosyl-(5')-3-methylthiopropylamine
  • S-Adenosyl(5')-3-methylthiopropylamine
  • (-)-S-Adenosyl-(5')-3-methylthiopropylamine
  • (-)-S-Adenosyl-(5’)-3-methylthiopropylamine
  • 5'-[(3-Aminopropyl)methylsulfonio]-5'-deoxyadenosine
  • 5’-[(3-aminopropyl)methylsulfonio]-5’-deoxyadenosine
  • S-Adenosyl-(5’)-3-methylthiopropylamine
  • S-Adenosyl-L-methionamine
  • S-Adenosylmethionamine
  • S-Methyl-S-adenosyl homocysteamine
  • S-Methyl-S-adenosylhomocysteamine
  • S-Methyladenosylhomocysteamine
CAS number22365-13-5
WeightAverage: 355.436
Monoisotopic: 355.155234322
InChI KeyZUNBITIXDCPNSD-LSRJEVITSA-N
InChIInChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/t8-,10-,11-,14-,24?/m1/s1
IUPAC Name{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-aminopropyl)methylsulfanium
Traditional IUPAC Namedecarboxylated sam
Chemical FormulaC14H23N6O3S
SMILES[H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])[S+](C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])N([H])[H])[C@@]1([H])O[H])N1C([H])=NC2=C1N=C([H])N=C2N([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Class5'-deoxyribonucleosides
Sub Class5'-deoxy-5'-thionucleosides
Direct Parent5'-deoxy-5'-thionucleosides
Alternative Parents
Substituents
  • 5'-deoxy-5'-thionucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.27 g/LALOGPS
logP0.28ALOGPS
logP-2.8ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)10.09ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area145.33 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.4 m³·mol⁻¹ChemAxon
Polarizability36.97 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
beta-Alanine metabolismPW002381 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
Cysteine and methionine metabolismec00270 Map00270
beta-Alanine metabolismec00410 Map00410
SMPDB Reactions
Putrescine + S-Adenosylmethioninamine → hydron + 5'-Methylthioadenosine + Spermidine
S-Adenosyl-L-methionine + hydron → S-Adenosylmethioninamine + Carbon dioxide
Spermidine + S-Adenosylmethioninamine → hydron + 5'-Methylthioadenosine + Spermine
KEGG Reactions
hydron + S-Adenosylmethionine → S-Adenosylmethioninamine + Carbon dioxide
Putrescine + S-Adenosylmethioninamine → Spermidine + hydron + 5'-Methylthioadenosine
Spermidine + S-Adenosylmethioninamine → Spermine + hydron + 5'-Methylthioadenosine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06wi-7923000000-45e056b479c0e2cba364JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ai-8291700000-8e1b09746b1c704e209fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_7) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0904000000-5a1b6a3a878c0630e6eaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-70103a635ebc7c51a985JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-3900000000-65b9306b33b0ffc5e9fcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0916000000-8fc88153f214f58b3dc2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-8c8ee467ecf1a037a37bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mx-7900000000-b79675da812011642f0bJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
Synthesis Reference:Pegg, Anthony E. Assay of aminopropyltransferases. Methods in Enzymology (1983), 94(Polyamines), 260-5.
External Links:
ResourceLink
CHEBI ID15625
HMDB IDHMDB00988
Pubchem Compound ID1078
Kegg IDC01137
ChemSpider ID25050861
FOODB IDFDB022353
WikipediaS-Adenosylmethioninamine
BioCyc IDS-ADENOSYLMETHIONINAMINE

Enzymes

Protein Details
1. Spermine synthase
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.
Protein Details
2. Spermidine synthase
General function:
Involved in catalytic activity
Specific function:
S-adenosylmethioninamine + putrescine = 5'-S- methyl-5'-thioadenosine + spermidine
Gene Name:
SPE3
Uniprot ID:
Q12074
Molecular weight:
33323.80078
Reactions
S-adenosylmethioninamine + putrescine → 5'-S-methyl-5'-thioadenosine + spermidine.
Protein Details
3. S-adenosylmethionine decarboxylase proenzyme
General function:
Involved in adenosylmethionine decarboxylase activity
Specific function:
S-adenosylmethionine decarboxylase is essential for normal growth, sporulation, maintenance of ds-RNA virus, biosynthesis of spermine and spermidine
Gene Name:
SPE2
Uniprot ID:
P21182
Molecular weight:
46232.0
Reactions
S-adenosyl-L-methionine → (5-deoxy-5-adenosyl)(3-aminopropyl)-methylsulfonium salt + CO(2).