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5'-Methylthioadenosine (YMDB00178)

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
MOLSDFPDBSMILESInChI
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-Adenosylmethioninamine → hydron + 5'-Methylthioadenosine + Spermidine
Spermidine + S-Adenosylmethioninamine → hydron + 5'-Methylthioadenosine + Spermine
KEGG Reactions
phosphate + 5'-Methylthioadenosine → S-Methyl-5-thio-alpha-D-ribose 1-phosphate + Adenine
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
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000i-0940000000-16b1106966ac98c7a107JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-0940000000-16b1106966ac98c7a107JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-0940000000-30fc68e7b5ff7576069bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01ti-0900000000-312bd8eec3c461e919f9JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9530000000-5fbf6b1a856ad3827980JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0h70-9636300000-67e425eba97fe420c464JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000j-0940000000-55655e7a0a6c8acba0f0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-f37865ca2029a623ace7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-2900000000-ae0e3df9bf25c100940dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-0090000000-72139812c5b2ede077edJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-0910000000-0c3d173f36272e3271ebJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-0900000000-f3443ca133811f52c5d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000i-1900000000-49cc299525d7fca27818JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-000i-3900000000-39bebdcaa7ce2695465bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-76b935f4f0a78c15ca0eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0002-4900000000-d8c0df43305b934d71dcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0900000000-d3bfbeb6fb95e3768ef6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0910000000-56784be58ef9065f21f6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0910000000-56784be58ef9065f21f6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0090000000-72139812c5b2ede077edJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0910000000-0c3d173f36272e3271ebJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-f3443ca133811f52c5d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-1900000000-6ec86a11bf8ad7331bd2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-3900000000-39bebdcaa7ce2695465bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-b9006ef8eecdaefc89a6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0940000000-eb168427f389d7079abfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-714e20a3376683008e65JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-cb0adab85341c49ced5bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9220000000-14da12fd68bc6d33eed9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4910000000-324b5daf65bdaa0d2bdbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-4900000000-14e9c89fcdd488f204aaJSpectraViewer
1D NMR1H 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
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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 IDFDB031156
Wikipedia IDNot Available
BioCyc ID5-METHYLTHIOADENOSINE

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. Multicopy enhancer of UAS2
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