Record Information
Version1.0
Creation date2011-09-21 00:14:29 UTC
Update date2020-09-17 15:38:49 UTC
Primary IDFDB022465
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 a strong basic compound (based on its pKa). 5'-Methylthioadenosine exists in all living species, ranging from bacteria to humans. 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 its interaction with 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. 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 chia, black elderberries, kumquats, jew's ears, and pine nuts. This could make 5'-methylthioadenosine a potential biomarker for the consumption of these foods. Adenosine with the hydroxy group at C-5' substituted with a methylthio (methylsulfanyl) group.
CAS Number2457-80-9
Structure
Thumb
Synonyms
SynonymSource
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-Methylthioadenosinehmdb
5'-(Methylthio)-5'-deoxyadenosinehmdb
5'-(Methylthio)adenosinehmdb
5'-Deoxy-5'-(methylthio)adenosinehmdb
5'-Methylthioadenosinehmdb
5'-S-methyl-5'-thio-Adenosinehmdb
5'-S-Methyl-5'-thioadenosinehmdb
9-(5-S-Methyl-5-thio-b-D-ribofuranosyl)-9H-purin-6-amineGenerator
9-(5-S-Methyl-5-thio-beta-D-ribofuranosyl)-9H-purin-6-amineChEBI
9-(5-S-Methyl-5-thio-β-D-ribofuranosyl)-9H-purin-6-amineGenerator
Methylthioadenosinehmdb
MTAhmdb
S-methyl-5-thioadenosinehmdb
S-methyl-5'-thioadenosinehmdb
Thiomethyladenosinehmdb
Predicted PropertiesNot Available
Chemical FormulaC11H15N5O3S
IUPAC name
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
ClassificationNot classified
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
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-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID388321
ChEMBL IDCHEMBL277041
KEGG Compound IDC00170
Pubchem Compound ID439176
Pubchem Substance IDNot Available
ChEBI ID17509
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01173
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34127
KNApSAcK IDNot Available
HET IDMTA
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
Enzymes
NameGene NameUniProt ID
Spermidine synthaseSRMP19623
Spermine synthaseSMSP52788
S-methyl-5'-thioadenosine phosphorylaseMTAPQ13126
Pathways
NameSMPDB LinkKEGG Link
Methionine MetabolismSMP00033 map00270
Spermidine and Spermine BiosynthesisSMP00445 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference