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Identification
YMDB IDYMDB00980
Name(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium
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 is a very strong basic compound (based on its pKa). S-Adenosylmethioninamine exists in all living species, ranging from bacteria to humans. Within yeast, S-adenosylmethioninamine participates in a number of enzymatic reactions. In particular, putrescine and S-adenosylmethioninamine can be converted into 5'-methylthioadenosine and spermidine through its interaction with the enzyme spermidine synthase. In addition, S-adenosylmethioninamine can be biosynthesized from S-adenosylmethionine through the action of the enzyme S-adenosylmethionine decarboxylase. In yeast, S-adenosylmethioninamine is involved in the metabolic pathway called the beta-alanine metabolism pathway.
Structure
Thumb
Synonyms
  • (5-deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt
  • (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
  • 3-amino-propyl-S-adenosine
  • dAdoMet
  • dcSAM
  • decarboxylated AdoMet
  • decarboxylated S-adenosylmethionine
  • decarboxylated SAM
  • S-Adenosyl-(5')-3-methylthiopropylamine
  • S-Adenosyl-3-methylthiopropylamine
  • s-adenosyl-l-methioninamine
  • S-adenosylmethioninamine
  • S-methyl-S-adenosyl homocysteamine
  • (5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium
  • 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
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
SMILESC[S+](CCCN)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
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 LocationsNot Available
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 ReactionsNot Available
KEGG ReactionsNot Available
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 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
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Tabor, C. W., Tabor, H. (1984). "Methionine adenosyltransferase (S-adenosylmethionine synthetase) and S-adenosylmethionine decarboxylase." Adv Enzymol Relat Areas Mol Biol 56:251-282.6364703
  • Pegg, A. E. (1986). "Recent advances in the biochemistry of polyamines in eukaryotes." Biochem J 234:249-262.3087344
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15625
HMDB IDHMDB00988
Pubchem Compound ID439415
Kegg IDC01137
ChemSpider ID25050861
FOODB IDFDB022353
Wikipedia IDS-Adenosylmethioninamine
BioCyc IDS-ADENOSYLMETHIONINAMINE

Enzymes

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).