Showing metabocard for 5'-Methylthioadenosine (MMDBc0000563)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:40:37 UTC
Update Date2024-10-13 06:56:09 UTC
Metabolite IDMMDBc0000563
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
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f46ba874850>

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3D MOL for #<Metabolite:0x00007f46ba874850>
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3D SDF for #<Metabolite:0x00007f46ba874850>
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3D-SDF for #<Metabolite:0x00007f46ba874850>
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PDB for #<Metabolite:0x00007f46ba874850>
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3D PDB for #<Metabolite:0x00007f46ba874850>
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SMILES for #<Metabolite:0x00007f46ba874850>
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INCHI for #<Metabolite:0x00007f46ba874850>
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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
Molecular FormulaC11H15N5O3S
Average Mass297.334
Monoisotopic Mass297.089560061
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILESNot Available
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