FComEx: 5'-Methylthioadenosine (PC000628)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:37 UTC

Update date

2017-01-19 02:36:30 UTC

FoodComEx ID

PC000628

FoodDB Record

FDB022465

Chemical Information

Name

5'-Methylthioadenosine

Description

5'-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 Number

2457-80-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-D-Ribofuranose	hmdb
1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-delta-Ribofuranose	hmdb
5-Methylthioadenosine	hmdb
5'-(Methylthio)-5'-deoxyadenosine	hmdb
5'-(Methylthio)adenosine	hmdb
5'-Deoxy-5'-(methylthio)adenosine	hmdb
5'-Methylthioadenosine	hmdb
5'-S-methyl-5'-thio-Adenosine	hmdb
5'-S-Methyl-5'-thioadenosine	hmdb
9-(5-S-Methyl-5-thio-b-D-ribofuranosyl)-9H-purin-6-amine	Generator
9-(5-S-Methyl-5-thio-beta-D-ribofuranosyl)-9H-purin-6-amine	ChEBI
9-(5-S-Methyl-5-thio-β-D-ribofuranosyl)-9H-purin-6-amine	Generator
Methylthioadenosine	hmdb
MTA	hmdb
S-methyl-5-thioadenosine	hmdb
S-methyl-5'-thioadenosine	hmdb
Thiomethyladenosine	hmdb

Chemical Formula

C11H15N5O3S

IUPAC name

(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol

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 Key

WUUGFSXJNOTRMR-IOSLPCCCSA-N

Isomeric SMILES

CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N

Average Molecular Weight

297.334

Monoisotopic Molecular Weight

297.089560061

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

5'-deoxyribonucleosides

Sub Class

5'-deoxy-5'-thionucleosides

Direct Parent

5'-deoxy-5'-thionucleosides

Alternative Parents