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Record Information
Version	2.0
Creation Date	2012-05-31 13:46:47 -0600
Update Date	2015-09-13 12:56:10 -0600
Secondary Accession Numbers	ECMDB01173
Identification
Name:	5'-Methylthioadenosine
Description	5-Methylthioadenosine is a normal metabolite in Cysteine and methionine metabolism. Spermidine synthase (putrescine aminopropyltransferase)(EC:2.5.1.16) catalyzes the its formation and it is then converted to 5-Methylthio-D-ribose via S-adenosylhomocysteine/5'-methylthioadenosine nucleosidase [EC:3.2.2.9]. (KEGG)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xacc77660> Close
Synonyms:	1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-b-D-ribofuranose 1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-b-delta-ribofuranose 1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-b-δ-ribofuranose 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 1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-β-D-ribofuranose 1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-β-δ-ribofuranose 5'-(Methylthio)-5'-deoxyadenosine 5'-(Methylthio)adenosine 5'-S-methyl-5'-thioadenosine 5'-Deoxy-5'-(methylthio)adenosine 5'-Methylthioadenosine 5'-S-Methyl-5'-thio-Adenosine 5'-S-Methyl-5'-thioadenosine 5-Methylthioadenosine S-methyl-adenosine Methylthioadenosine MTA S-Methyl-5'-thioadenosine S-Methyl-5-thioadenosine S-Methyl-adenosine Thiomethyladenosine
Chemical Formula:	C11H15N5O3S
Weight:	Average: 297.334 Monoisotopic: 297.089560061
InChI Key:	WUUGFSXJNOTRMR-IOSLPCCCSA-N
InChI:	InChI=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
CAS number:	2457-80-9
IUPAC Name:	(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
Traditional IUPAC Name:	methylthioadenosine
SMILES:	CSC[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.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	5'-deoxyribonucleosides
Sub Class	5'-deoxy-5'-thionucleosides
Direct Parent	5'-deoxy-5'-thionucleosides
Alternative Parents	Glycosylamines 6-aminopurines Pentoses Aminopyrimidines and derivatives Imidolactams N-substituted imidazoles Tetrahydrofurans Heteroaromatic compounds 1,2-diols Secondary alcohols Dialkylthioethers Azacyclic compounds Sulfenyl compounds Oxacyclic compounds Organopnictogen compounds Hydrocarbon derivatives Primary amines
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 Framework	Aromatic heteropolycyclic compounds
External Descriptors	thioadenosine (CHEBI:17509 )
Physical Properties
State:	Solid
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 6.5 g/L ALOGPS logP -0.14 ALOGPS logP -0.61 ChemAxon logS -1.7 ALOGPS pKa (Strongest Acidic) 12.47 ChemAxon pKa (Strongest Basic) 3.92 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 119.31 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 74.03 m³·mol⁻¹ ChemAxon Polarizability 29.26 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	S-Adenosylmethioninamine + Putrescine + Ethylenediamine <> 5'-Methylthioadenosine + Hydrogen ion + Spermidine Cadaverine + S-Adenosylmethioninamine > 5'-Methylthioadenosine + Hydrogen ion + Aminopropylcadaverine 5'-Methylthioadenosine + Water > 5-Methylthioribose + Adenine 5'-Methylthioadenosine + Water <> Adenine + 5-Methylthioribose S-Adenosylmethioninamine + Putrescine <> 5'-Methylthioadenosine + Spermidine S-Adenosylmethioninamine + Spermidine <> 5'-Methylthioadenosine + Spermine S-Adenosylmethioninamine + Cadaverine <> 5'-Methylthioadenosine + Aminopropylcadaverine Putrescine + S-Adenosylmethioninamine > Hydrogen ion + Spermidine + 5'-Methylthioadenosine 5'-Methylthioadenosine + Water > S-methyl-5-thio-D-ribose + Adenine S-Adenosylmethioninamine + Putrescine > 5'-Methylthioadenosine + Spermidine Cadaverine + Decarboxy-SAM > Aminopropylcadaverine + 5'-Methylthioadenosine + Hydrogen ion Decarboxy-SAM + Putrescine > 5'-Methylthioadenosine + Spermidine + Hydrogen ion S-Adenosylmethioninamine + Putrescine + Ethylenediamine <>5 5'-Methylthioadenosine + Hydrogen ion + Spermidine Cadaverine + S-Adenosylmethioninamine >5 5'-Methylthioadenosine + Hydrogen ion + Aminopropylcadaverine S-Adenosylmethioninamine + Putrescine + Ethylenediamine <>5 5'-Methylthioadenosine + Hydrogen ion + Spermidine
SMPDB Pathways:	Glutathione metabolism PW000833 Spermidine Biosynthesis I PW002040 aminopropylcadaverine biosynthesis PW002039 beta-Alanine metabolism PW000896
KEGG Pathways:	Arginine and proline metabolism ec00330 Cysteine and methionine metabolism ec00270 Glutathione metabolism ec00480 Metabolic pathways eco01100 beta-Alanine metabolism ec00410
EcoCyc Pathways:	S-methyl-5'-thioadenosine degradation IV PWY0-1391 aminopropylcadaverine biosynthesis PWY0-1303 spermidine biosynthesis I BSUBPOLYAMSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-000i-0940000000-16b1106966ac98c7a107 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-000i-0940000000-16b1106966ac98c7a107 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-000i-0940000000-30fc68e7b5ff7576069b View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-01ti-0900000000-312bd8eec3c461e919f9 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-056r-9530000000-5fbf6b1a856ad3827980 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-0h70-9636300000-67e425eba97fe420c464 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-000j-0940000000-55655e7a0a6c8acba0f0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-000i-1900000000-f37865ca2029a623ace7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-000i-2900000000-ae0e3df9bf25c100940d View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive splash10-0002-0090000000-72139812c5b2ede077ed View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive splash10-000i-0910000000-0c3d173f36272e3271eb View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive splash10-000i-0900000000-f3443ca133811f52c5d7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive splash10-000i-1900000000-49cc299525d7fca27818 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive splash10-000i-3900000000-39bebdcaa7ce2695465b View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive splash10-000i-0900000000-76b935f4f0a78c15ca0e View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive splash10-0002-4900000000-d8c0df43305b934d71dc View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-000i-0900000000-d3bfbeb6fb95e3768ef6 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative splash10-001i-0910000000-56784be58ef9065f21f6 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , negative splash10-001i-0910000000-56784be58ef9065f21f6 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-0002-0090000000-72139812c5b2ede077ed View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-000i-0910000000-0c3d173f36272e3271eb View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-000i-0900000000-f3443ca133811f52c5d7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-000i-1900000000-6ec86a11bf8ad7331bd2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-000i-3900000000-39bebdcaa7ce2695465b View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-IT , positive splash10-000i-0900000000-b9006ef8eecdaefc89a6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-0940000000-eb168427f389d7079abf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0900000000-714e20a3376683008e65 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-2900000000-cb0adab85341c49ced5b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0002-9220000000-14da12fd68bc6d33eed9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-4910000000-324b5daf65bdaa0d2bdb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-053r-4900000000-14e9c89fcdd488f204aa View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Avila MA, Garcia-Trevijano ER, Lu SC, Corrales FJ, Mato JM: Methylthioadenosine. Int J Biochem Cell Biol. 2004 Nov;36(11):2125-30. Pubmed: 15313459 Contreres JO, Dupuy E, Job B, Habib A, Bryckaert M, Rosa JP, Simoneau G, Herbert JM, Savi P, Levy-Toledano S: Effect of clopidogrel administration to healthy volunteers on platelet phosphorylation events triggered by ADP. Br J Haematol. 2003 Feb;120(4):633-42. Pubmed: 12588350 Gerasimovskaya EV, Ahmad S, White CW, Jones PL, Carpenter TC, Stenmark KR: Extracellular ATP is an autocrine/paracrine regulator of hypoxia-induced adventitial fibroblast growth. Signaling through extracellular signal-regulated kinase-1/2 and the Egr-1 transcription factor. J Biol Chem. 2002 Nov 22;277(47):44638-50. Epub 2002 Sep 18. Pubmed: 12244041 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. Pubmed: 9129323 Mills GC, Mills JS: Urinary excretion of methylthioadenosine in immunodeficient children. Clin Chim Acta. 1985 Mar 30;147(1):15-23. Pubmed: 3987052 Mills GC, Schmalstieg FC, Goldblum RM: Urinary excretion of modified purines and nucleosides in immunodeficient children. Biochem Med. 1985 Aug;34(1):37-51. Pubmed: 4052062 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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.
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 17509 HMDB ID HMDB01173 Pubchem Compound ID 149 Kegg ID C00170 ChemSpider ID 388321 Wikipedia ID Not Available BioCyc ID 5-METHYLTHIOADENOSINE EcoCyc ID 5-METHYLTHIOADENOSINE Ligand Expo MTA

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