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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 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
  • 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
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-Adenosylmethioninaminehydron + 5'-Methylthioadenosine + Spermidine
S-Adenosyl-L-methionine + hydronS-Adenosylmethioninamine + Carbon dioxide
Spermidine + S-Adenosylmethioninaminehydron + 5'-Methylthioadenosine + Spermine
KEGG Reactions
hydron + S-AdenosylmethionineS-Adenosylmethioninamine + Carbon dioxide
Putrescine + S-AdenosylmethioninamineSpermidine + hydron + 5'-Methylthioadenosine
Spermidine + S-AdenosylmethioninamineSpermine + hydron + 5'-Methylthioadenosine
Concentrations
Intracellular ConcentrationsNot Available
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
  • 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

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.
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.
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).