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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:45:41 UTC
HMDB IDHMDB0001173
Secondary Accession Numbers
  • HMDB01173
Metabolite Identification
Common Name5'-Methylthioadenosine
Description5'-Methylthioadenosine, also known as MTA or thiomethyladenosine, 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. 5'-Methylthioadenosine is metabolized solely by MTA-phosphorylase, to yield 5-methylthioribose-1-phosphate and adenine, a crucial step in the methionine and purine salvage pathways, respectively. 5'-Methylthioadenosine exists in all living species, ranging from bacteria to humans. 5'-Methylthioadenosine (MTA) is a naturally occurring sulfur-containing nucleoside present in all mammalian tissues. Within humans, 5'-methylthioadenosine participates in a number of enzymatic reactions. In particular, 5'-methylthioadenosine and spermidine can be biosynthesized from S-adenosylmethioninamine and putrescine through the action of the enzyme spermidine synthase. In addition, 5'-methylthioadenosine can be converted into 5-methylthioribose 1-phosphate and L-methionine; which is catalyzed by the enzyme S-methyl-5'-thioadenosine phosphorylase. It is produced from S-adenosylmethionine mainly through the polyamine biosynthetic pathway, where it behaves as a powerful inhibitory product. For instance, 5'-Methylthioadenosine has been shown to influence the regulation of gene expression, proliferation, differentiation, and apoptosis (PMID:15313459 ). In humans, 5'-methylthioadenosine is involved in the metabolic disorder called hypermethioninemia. Outside of the human body, 5'-Methylthioadenosine has been detected, but not quantified in several different foods, such as soursops, allspices, summer grapes, alaska wild rhubarbs, and breadfruits. Elevated excretion appears in children with severe combined immunodeficiency syndrome (SCID) (PMID:3987052 ). Evidence suggests that 5'-Methylthioadenosine can affect cellular processes in many ways. 5'-Methylthioadenosine can be found in human urine.
Structure
Data?1582752181
Synonyms
ValueSource
5'-Deoxy-5'-(methylthio)adenosineChEBI
5-MethylthioadenosineChEBI
9-(5-S-Methyl-5-thio-beta-D-ribofuranosyl)-9H-purin-6-amineChEBI
MethylthioadenosineChEBI
MTAChEBI
S-Methyl-5'-thioadenosineChEBI
ThiomethyladenosineChEBI
9-(5-S-Methyl-5-thio-b-D-ribofuranosyl)-9H-purin-6-amineGenerator
9-(5-S-Methyl-5-thio-β-D-ribofuranosyl)-9H-purin-6-amineGenerator
1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-D-ribofuranoseHMDB
1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-delta-ribofuranoseHMDB
5'-(Methylthio)-5'-deoxyadenosineHMDB
5'-(Methylthio)adenosineHMDB
5'-S-Methyl-5'-thio-adenosineHMDB
5'-S-Methyl-5'-thioadenosineHMDB
S-Methyl-5-thioadenosineHMDB
Adenine(5'-deoxy-5'-methylthio)9-beta-D-furanoribosideHMDB
5-MTDAHMDB
5'-Methylthio-5'-deoxyadenosineHMDB
5'-Deoxy-5'-methylthioadenosineHMDB
5'-Methylthioadenosine, methyl-(14)C-labeledHMDB
5'-MethylthioadenosineChEBI
Chemical FormulaC11H15N5O3S
Average Molecular Weight297.334
Monoisotopic Molecular Weight297.089560061
IUPAC Name(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
Traditional Namemethylthioadenosine
CAS Registry Number2457-80-9
SMILES
CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
InChI Identifier
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
InChI KeyWUUGFSXJNOTRMR-IOSLPCCCSA-N
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
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M-H]-Baker170.34430932474
DeepCCS[M+H]+Baker173.02530932474
AllCCS[M-H]-Not Available168.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00000159
AllCCS[M+H]+Not Available167.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00000159
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.5 g/LALOGPS
logP10(-0.14) g/LALOGPS
logP10(-0.61) g/LChemAxon
logS10(-1.7) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+170.20631661259
DarkChem[M-H]-164.81631661259
AllCCS[M+H]+167.31732859911
AllCCS[M-H]-165.60232859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5'-Methylthioadenosine,1TMS,#1CSC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O2746.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
5'-Methylthioadenosine,1TMS,#2CSC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C2744.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
5'-Methylthioadenosine,1TMS,#3CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O2775.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
5'-Methylthioadenosine,2TMS,#1CSC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2689.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
5'-Methylthioadenosine,2TMS,#2CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O2743.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
5'-Methylthioadenosine,2TMS,#3CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C2738.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
5'-Methylthioadenosine,2TMS,#4CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O2733.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
5'-Methylthioadenosine,1TBDMS,#1CSC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2964.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
5'-Methylthioadenosine,1TBDMS,#2CSC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2959.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
5'-Methylthioadenosine,1TBDMS,#3CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O2958.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
5'-Methylthioadenosine,2TBDMS,#1CSC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3099.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
5'-Methylthioadenosine,2TBDMS,#2CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3098.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
5'-Methylthioadenosine,2TBDMS,#3CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3088.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
5'-Methylthioadenosine,2TBDMS,#4CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O3120.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5'-Methylthioadenosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000i-0940000000-16b1106966ac98c7a1072014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5'-Methylthioadenosine GC-EI-TOF (Non-derivatized)splash10-000i-0940000000-16b1106966ac98c7a1072017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5'-Methylthioadenosine GC-EI-TOF (Non-derivatized)splash10-000i-0940000000-30fc68e7b5ff7576069b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5'-Methylthioadenosine GC-EI-TOF (Non-derivatized)splash10-01ti-0900000000-312bd8eec3c461e919f92017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5'-Methylthioadenosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9530000000-5fbf6b1a856ad38279802017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5'-Methylthioadenosine GC-MS (2 TMS) - 70eV, Positivesplash10-0h70-9636300000-67e425eba97fe420c4642017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5'-Methylthioadenosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5'-Methylthioadenosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-001i-0910000000-56784be58ef9065f21f62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QTOF , negative-QTOFsplash10-001i-0910000000-56784be58ef9065f21f62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine 35V, Negative-QTOFsplash10-001i-0900000000-5f5ce891d3b31bea8dff2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine 35V, Negative-QTOFsplash10-001i-0900000000-d819212647c26720bdfc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine 10V, Negative-QTOFsplash10-001i-0900000000-8ac1758f0ac9c7d7a1c82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine 20V, Negative-QTOFsplash10-001i-0900000000-d152916d09f6a5e551942021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine 40V, Negative-QTOFsplash10-001i-0900000000-ffdaf4c3fd84e8313a822021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000j-0940000000-55655e7a0a6c8acba0f02012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000i-1900000000-f37865ca2029a623ace72012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-000i-2900000000-ae0e3df9bf25c100940d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0002-0090000000-72139812c5b2ede077ed2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-000i-0910000000-0c3d173f36272e3271eb2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-000i-0900000000-f3443ca133811f52c5d72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-000i-1900000000-49cc299525d7fca278182012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-000i-3900000000-39bebdcaa7ce2695465b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-000i-0900000000-76b935f4f0a78c15ca0e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0002-4900000000-d8c0df43305b934d71dc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-000i-0900000000-d3bfbeb6fb95e3768ef62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ , positive-QTOFsplash10-0002-0090000000-72139812c5b2ede077ed2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ , positive-QTOFsplash10-000i-0910000000-0c3d173f36272e3271eb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ , positive-QTOFsplash10-000i-0900000000-f3443ca133811f52c5d72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ , positive-QTOFsplash10-000i-1900000000-6ec86a11bf8ad7331bd22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ , positive-QTOFsplash10-000i-3900000000-39bebdcaa7ce2695465b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-IT , positive-QTOFsplash10-000i-0900000000-b9006ef8eecdaefc89a62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-949c013f4e9edec10cb92017-09-14HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Fibroblasts
  • Placenta
  • Platelet
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.12 +/- 0.05 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.12 +/- 0.08 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.13 +/- 0.11 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB02282
Phenol Explorer Compound IDNot Available
FooDB IDFDB031156
KNApSAcK IDNot Available
Chemspider ID388321
KEGG Compound IDC00170
BioCyc ID5-METHYLTHIOADENOSINE
BiGG ID34127
Wikipedia LinkNot Available
METLIN ID3425
PubChem Compound439176
PDB IDNot Available
ChEBI ID17509
Food Biomarker OntologyNot Available
VMH ID5MTA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSufrin, 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)
General References
  1. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. 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 ]
  3. 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 ]
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Enzymes

General function:
Involved in spermine synthase activity
Specific function:
Catalyzes the production of spermine from spermidine and decarboxylated S-adenosylmethionine (dcSAM).
Gene Name:
SMS
Uniprot ID:
P52788
Molecular weight:
35278.2
Reactions
S-Adenosylmethioninamine + Spermidine → 5'-Methylthioadenosine + Sperminedetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the production of spermidine from putrescine and decarboxylated S-adenosylmethionine (dcSAM). Has a strong preference for putrescine as substrate, and has very low activity towards 1,3-diaminopropane. Has extremely low activity towards spermidine.
Gene Name:
SRM
Uniprot ID:
P19623
Molecular weight:
33824.455
Reactions
S-Adenosylmethioninamine + Putrescine → 5'-Methylthioadenosine + Spermidinedetails
S-Adenosylmethioninamine + Spermidine → 5'-Methylthioadenosine + Sperminedetails
S-Adenosylmethioninamine + Cadaverine → 5'-Methylthioadenosine + Aminopropylcadaverinedetails
General function:
Involved in transferase activity, transferring pentosyl groups
Specific function:
Catalyzes the reversible phosphorylation of S-methyl-5'-thioadenosine (MTA) to adenine and 5-methylthioribose-1-phosphate. Involved in the breakdown of MTA, a major by-product of polyamine biosynthesis. Responsible for the first step in the methionine salvage pathway after MTA has been generated from S-adenosylmethionine. Has broad substrate specificity with 6-aminopurine nucleosides as preferred substrates.
Gene Name:
MTAP
Uniprot ID:
Q13126
Molecular weight:
31235.76
Reactions
5'-Methylthioadenosine + Phosphate → Adenine + 5-Methylthioribose 1-phosphatedetails