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Identification
YMDB IDYMDB00178
Name5'-Methylthioadenosine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5'-Methylthioadenosine (MTA) is a side product in the biosynthesis of several important compounds. An important case is polyamine synthesis, where L-methionine is consumed through the utilization of S-adenosyl-L-methionine (SAM) in a reaction that releases MTA in the superpathway of polyamine biosynthesis. 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. MTA is recycled back to L-methionine during the methionine salvage pathway, which is found in a wide variety of organisms, including bacteria, protozoa, plants and mammals. [Biocyc PWY-6754 and POLYAMINSYN3-PWY and PWY-4361]
Structure
Thumb
Synonyms
  • 1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-D-Ribofuranose
  • 1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-delta-Ribofuranose
  • 5-Methylthioadenosine
  • 5'-(Methylthio)-5'-deoxyadenosine
  • 5'-(Methylthio)adenosine
  • 5'-Deoxy-5'-(methylthio)adenosine
  • 5'-Methylthioadenosine
  • 5'-S-methyl-5'-thio-Adenosine
  • 5'-S-Methyl-5'-thioadenosine
  • Methylthioadenosine
  • MTA
  • S-methyl-5-thioadenosine
  • S-methyl-5'-thioadenosine
  • Thiomethyladenosine
  • 9-(5-S-Methyl-5-thio-beta-D-ribofuranosyl)-9H-purin-6-amine
  • 9-(5-S-Methyl-5-thio-b-D-ribofuranosyl)-9H-purin-6-amine
  • 9-(5-S-Methyl-5-thio-β-D-ribofuranosyl)-9H-purin-6-amine
  • Adenine(5'-deoxy-5'-methylthio)9-beta-D-furanoriboside
  • 5-MTDA
  • 5'-Methylthio-5'-deoxyadenosine
  • 5'-Deoxy-5'-methylthioadenosine
  • 5'-Methylthioadenosine, methyl-(14)C-labeled
CAS number2457-80-9
WeightAverage: 297.334
Monoisotopic: 297.089560061
InChI KeyWUUGFSXJNOTRMR-IOSLPCCCSA-N
InChIInChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
IUPAC Name(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
Traditional IUPAC Namemethylthioadenosine
Chemical FormulaC11H15N5O3S
SMILES[H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])SC([H])([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
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Azole
  • Tetrahydrofuran
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Organoheterocyclic compound
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Azacycle
  • Oxacycle
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.5 g/LALOGPS
logP-0.14ALOGPS
logP-0.61ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)12.47ChemAxon
pKa (Strongest Basic)3.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area119.31 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.03 m³·mol⁻¹ChemAxon
Polarizability29.26 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
Methionine metabolism and salvagePW002384 ThumbThumb?image type=greyscaleThumb?image type=simple
beta-Alanine metabolismPW002381 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Cysteine and methionine metabolismec00270 Map00270
beta-Alanine metabolismec00410 Map00410
SMPDB Reactions
Putrescine + S-Adenosylmethioninaminehydron + 5'-Methylthioadenosine + Spermidine
Spermidine + S-Adenosylmethioninaminehydron + 5'-Methylthioadenosine + Spermine
KEGG Reactions
phosphate + 5'-MethylthioadenosineS-Methyl-5-thio-alpha-D-ribose 1-phosphate + Adenine
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
  • 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
  • Subhi, A. L., Diegelman, P., Porter, C. W., Tang, B., Lu, Z. J., Markham, G. D., Kruger, W. D. (2003). "Methylthioadenosine phosphorylase regulates ornithine decarboxylase by production of downstream metabolites." J Biol Chem 278:49868-49873.14506228
Synthesis Reference:Sufrin, Janice R.; Spiess, Arthur J.; Kramer, Debora L.; Libby, Paul R.; Porter, Carl W. Synthesis and antiproliferative effects of novel 5'-fluorinated analogs of 5'-deoxy-5'-(methylthio)adenosine. Journal of Medicinal Chemistry (1989), 32(5), 997-1001.
External Links:
ResourceLink
CHEBI ID17509
HMDB IDHMDB01173
Pubchem Compound ID149
Kegg IDC00170
ChemSpider ID388321
FOODB IDFDB022465
Wikipedia IDNot Available
BioCyc ID5-METHYLTHIOADENOSINE

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 catalytic activity
Specific function:
Seems to be implicated in the regulation of the expression of the ADH2 gene
Gene Name:
MEU1
Uniprot ID:
Q07938
Molecular weight:
37856.30078
Reactions
S-methyl-5'-thioadenosine + phosphate → adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate