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Showing Compound S-methyl-5'-thioadenosine (FDB031156)

Record Information
Version1.0
Creation date2015-05-07 21:10:34 UTC
Update date2019-11-26 03:22:10 UTC
Primary IDFDB031156
Secondary Accession Numbers
  • FDB022465
Chemical Information
FooDB NameS-methyl-5'-thioadenosine
Description5'-deoxy-5'-methylthioadenosine, also known as S-methyl-5'-thioadenosine or mta, is a member of the class of compounds known as 5'-deoxy-5'-thionucleosides. 5'-deoxy-5'-thionucleosides are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. 5'-deoxy-5'-methylthioadenosine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5'-deoxy-5'-methylthioadenosine can be found in a number of food items such as allspice, sesame, roselle, and bayberry, which makes 5'-deoxy-5'-methylthioadenosine a potential biomarker for the consumption of these food products. 5'-deoxy-5'-methylthioadenosine can be found primarily in blood and urine, as well as in human fibroblasts, platelet and prostate tissues. 5'-deoxy-5'-methylthioadenosine exists in all living species, ranging from bacteria to humans. In humans, 5'-deoxy-5'-methylthioadenosine is involved in a couple of metabolic pathways, which include methionine metabolism and spermidine and spermine biosynthesis. 5'-deoxy-5'-methylthioadenosine is also involved in several metabolic disorders, some of which include glycine n-methyltransferase deficiency, methionine adenosyltransferase deficiency, homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblg complementation type, and hypermethioninemia.
CAS Number2457-80-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H15N5O3S
IUPAC name(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
InChI IdentifierInChI=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
Isomeric SMILESCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
Average Molecular Weight297.334
Monoisotopic Molecular Weight297.089560061
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS5'-Methylthioadenosine, non-derivatized, GC-MS Spectrumsplash10-000i-0940000000-16b1106966ac98c7a107Spectrum
GC-MS5'-Methylthioadenosine, non-derivatized, GC-MS Spectrumsplash10-000i-0940000000-16b1106966ac98c7a107Spectrum
GC-MS5'-Methylthioadenosine, non-derivatized, GC-MS Spectrumsplash10-000i-0940000000-30fc68e7b5ff7576069bSpectrum
GC-MS5'-Methylthioadenosine, non-derivatized, GC-MS Spectrumsplash10-01ti-0900000000-312bd8eec3c461e919f9Spectrum
Predicted GC-MS5'-Methylthioadenosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056r-9530000000-5fbf6b1a856ad3827980Spectrum
Predicted GC-MS5'-Methylthioadenosine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0h70-9636300000-67e425eba97fe420c464Spectrum
Predicted GC-MS5'-Methylthioadenosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5'-Methylthioadenosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000j-0940000000-55655e7a0a6c8acba0f02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-f37865ca2029a623ace72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-2900000000-ae0e3df9bf25c100940d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-0090000000-72139812c5b2ede077ed2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-0910000000-0c3d173f36272e3271eb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-0900000000-f3443ca133811f52c5d72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000i-1900000000-49cc299525d7fca278182012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-000i-3900000000-39bebdcaa7ce2695465b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-76b935f4f0a78c15ca0e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0002-4900000000-d8c0df43305b934d71dc2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0900000000-d3bfbeb6fb95e3768ef62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0910000000-56784be58ef9065f21f62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0910000000-56784be58ef9065f21f62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0090000000-72139812c5b2ede077ed2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0910000000-0c3d173f36272e3271eb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-f3443ca133811f52c5d72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-1900000000-6ec86a11bf8ad7331bd22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-3900000000-39bebdcaa7ce2695465b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-b9006ef8eecdaefc89a62017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0940000000-eb168427f389d7079abf2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-714e20a3376683008e652016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-cb0adab85341c49ced5b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9220000000-14da12fd68bc6d33eed92016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4910000000-324b5daf65bdaa0d2bdb2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-4900000000-14e9c89fcdd488f204aa2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference