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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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker170.34430932474
[M+H]+Baker173.02530932474
[M-H]-Not Available168.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00000159
[M+H]+Not Available167.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00000159
Predicted Molecular 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
Predicted Chromatographic 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
DeepCCS[M+H]+158.49230932474
DeepCCS[M-H]-156.09730932474
DeepCCS[M-2H]-190.39530932474
DeepCCS[M+Na]+165.06430932474
AllCCS[M+H]+167.332859911
AllCCS[M+H-H2O]+164.132859911
AllCCS[M+NH4]+170.332859911
AllCCS[M+Na]+171.132859911
AllCCS[M-H]-165.632859911
AllCCS[M+Na-2H]-165.332859911
AllCCS[M+HCOO]-165.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5'-MethylthioadenosineCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N3690.3Standard polar33892256
5'-MethylthioadenosineCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N2644.9Standard non polar33892256
5'-MethylthioadenosineCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N2798.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5'-Methylthioadenosine,1TMS,isomer #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 polar33892256
5'-Methylthioadenosine,1TMS,isomer #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 polar33892256
5'-Methylthioadenosine,1TMS,isomer #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 polar33892256
5'-Methylthioadenosine,2TMS,isomer #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 polar33892256
5'-Methylthioadenosine,2TMS,isomer #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 polar33892256
5'-Methylthioadenosine,2TMS,isomer #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 polar33892256
5'-Methylthioadenosine,2TMS,isomer #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 polar33892256
5'-Methylthioadenosine,3TMS,isomer #1CSC[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]1O[Si](C)(C)C2739.7Semi standard non polar33892256
5'-Methylthioadenosine,3TMS,isomer #1CSC[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]1O[Si](C)(C)C2769.4Standard non polar33892256
5'-Methylthioadenosine,3TMS,isomer #1CSC[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]1O[Si](C)(C)C3998.1Standard polar33892256
5'-Methylthioadenosine,3TMS,isomer #2CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O2744.4Semi standard non polar33892256
5'-Methylthioadenosine,3TMS,isomer #2CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O2825.2Standard non polar33892256
5'-Methylthioadenosine,3TMS,isomer #2CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O3755.0Standard polar33892256
5'-Methylthioadenosine,3TMS,isomer #3CSC[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]1O[Si](C)(C)C2733.0Semi standard non polar33892256
5'-Methylthioadenosine,3TMS,isomer #3CSC[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]1O[Si](C)(C)C2817.3Standard non polar33892256
5'-Methylthioadenosine,3TMS,isomer #3CSC[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]1O[Si](C)(C)C3702.1Standard polar33892256
5'-Methylthioadenosine,4TMS,isomer #1CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2759.5Semi standard non polar33892256
5'-Methylthioadenosine,4TMS,isomer #1CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2839.7Standard non polar33892256
5'-Methylthioadenosine,4TMS,isomer #1CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3414.5Standard polar33892256
5'-Methylthioadenosine,1TBDMS,isomer #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 polar33892256
5'-Methylthioadenosine,1TBDMS,isomer #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 polar33892256
5'-Methylthioadenosine,1TBDMS,isomer #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 polar33892256
5'-Methylthioadenosine,2TBDMS,isomer #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 polar33892256
5'-Methylthioadenosine,2TBDMS,isomer #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 polar33892256
5'-Methylthioadenosine,2TBDMS,isomer #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 polar33892256
5'-Methylthioadenosine,2TBDMS,isomer #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 polar33892256
5'-Methylthioadenosine,3TBDMS,isomer #1CSC[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]1O[Si](C)(C)C(C)(C)C3298.2Semi standard non polar33892256
5'-Methylthioadenosine,3TBDMS,isomer #1CSC[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]1O[Si](C)(C)C(C)(C)C3388.9Standard non polar33892256
5'-Methylthioadenosine,3TBDMS,isomer #1CSC[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]1O[Si](C)(C)C(C)(C)C4073.9Standard polar33892256
5'-Methylthioadenosine,3TBDMS,isomer #2CSC[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[Si](C)(C)C(C)(C)C)[C@@H]1O3265.8Semi standard non polar33892256
5'-Methylthioadenosine,3TBDMS,isomer #2CSC[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[Si](C)(C)C(C)(C)C)[C@@H]1O3445.2Standard non polar33892256
5'-Methylthioadenosine,3TBDMS,isomer #2CSC[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[Si](C)(C)C(C)(C)C)[C@@H]1O3846.1Standard polar33892256
5'-Methylthioadenosine,3TBDMS,isomer #3CSC[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]1O[Si](C)(C)C(C)(C)C3254.8Semi standard non polar33892256
5'-Methylthioadenosine,3TBDMS,isomer #3CSC[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]1O[Si](C)(C)C(C)(C)C3441.8Standard non polar33892256
5'-Methylthioadenosine,3TBDMS,isomer #3CSC[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]1O[Si](C)(C)C(C)(C)C3805.5Standard polar33892256
5'-Methylthioadenosine,4TBDMS,isomer #1CSC[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[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3460.7Semi standard non polar33892256
5'-Methylthioadenosine,4TBDMS,isomer #1CSC[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[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3592.9Standard non polar33892256
5'-Methylthioadenosine,4TBDMS,isomer #1CSC[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[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3688.6Standard polar33892256
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
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
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 ]
  4. 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 ]
  5. Mills GC, Mills JS: Urinary excretion of methylthioadenosine in immunodeficient children. Clin Chim Acta. 1985 Mar 30;147(1):15-23. [PubMed:3987052 ]
  6. 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 ]
  7. 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 ]
  8. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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