5'-Methylthioadenosine (BioCAD00000005016)
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Metabolite Card
Formula: C11H15N5O3S (297.0896)
SMILES: CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
Synonyms [en]
5'-methylthioadenosine; 5'-deoxy-5'-(methylthio)adenosine; Methylthioadenosine; Thiomethyladenosine; MTA; 5-Methylthioadenosine
Last reviewed on 2024-06-28.
Cite this Page
5'-Methylthioadenosine. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000005016). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
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 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.
DBLinks
- CAS Registry Number: 2457-80-9
- PubChem CID: 439176
- ChEBI: 17509
- HMDB: HMDB0001173
- LipidMaps:
- KEGG: C00170
- BioCyc: 5-METHYLTHIOADENOSINE
- NCBI MeSH: 5'-methylthioadenosine
- Wikipedia: 5%E2%80%B2-Methylthioadenosine
Other DBLinks
- CAS Registry Number: 2457-80-9
- CAS Registry Number: 2457-81-0
- CAS Registry Number: 5'-Deoxy-5'-methylthioadenosine - CAS 2457-80-9
- PubChem: 3470
- PubChem: 439176
- ChEBI: ChEBI:17509
- ChEBI: ChEBI:180963
- HMDB: HMDB0001173
- HMDB: HMDB01173
- KEGG: C00170
- BioCyc: 5-METHYLTHIOADENOSINE
- NCBI MeSH: 5'-methylthioadenosine
- Wikipedia: 5%E2%80%B2-Methylthioadenosine
- DrugBank: DB02282
- RefMet: RM0136067
- MoNA: CCMSLIB00000577895
- MoNA: CCMSLIB00000578116
- MoNA: CCMSLIB00005720332
- MoNA: FiehnHILIC000114
- MoNA: FiehnHILIC001008
- MoNA: FiehnHILIC001694
- MoNA: FiehnHILIC002543
- MoNA: FiehnLib000200
- MoNA: FiehnLib000201
- MoNA: HMDB0001173_ms_ms_1448
- MoNA: HMDB0001173_ms_ms_1449
- MoNA: HMDB0001173_ms_ms_1450
- MoNA: KO002721
- MoNA: KO002722
- MoNA: KO002723
- MoNA: KO002724
- MoNA: KO002725
- MoNA: KO008945
- MoNA: KO008946
- MoNA: ML002001
- MoNA: MoNA002199
- MoNA: MoNA002200
- MoNA: MoNA002201
- MoNA: MoNA032428
- MoNA: MoNA032430
- MoNA: MoNA032431
- MoNA: MoNA034474
- MoNA: MoNA034476
- MoNA: MoNA034479
- MoNA: MoNA037292
- MoNA: MoNA038024
- MoNA: OUF00082
- MoNA: PR100311
- MoNA: PR100743
- MoNA: PS067501
- MoNA: PS067502
- MoNA: PS067503
- MoNA: PS067504
- MoNA: PS067505
- MoNA: PS067506
- MoNA: PT106750
- MoNA: PT206750
- Metlin: METLIN_3425
- Coconut NaturalProduct: CNP0141020.1
Class / Ontology
- WishartLab ClassyFire: [5'-deoxy-5'-thionucleosides] 5'-deoxy-5'-thionucleosides
- RefMet: [Purine ribonucleosides] Purine ribonucleosides
- ChEBI: [CHEBI:17509] 5'-S-methyl-5'-thioadenosine
- ChEBI: [CHEBI:180963] beta-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-
- Coconut NaturalProduct: [Purine nucleos(t)ides] Purine nucleos(t)ides
| ID | EC Number | Name |
|---|---|---|
| KEGG:R00075 | 2.5.1.43 | S-adenosyl-L-methionine:S-adenosyl-L-methionine 3-amino-3-carboxypropyltransferase |
| KEGG:R00179 | 4.4.1.14 | S-adenosyl-L-methionine methylthioadenosine-lyase (1-aminocyclopropane-1-carboxylate-forming) |
| KEGG:R01401 | 3.2.2.9 | methylthioadenosine methylthioribohydrolase |
| KEGG:R01402 | 2.4.2.28 | S-methyl-5'-thioadenosine:phosphate S-methyl-5-thio-alpha-D-ribosyl-transferase |
| KEGG:R01920 | 2.5.1.16 | S-adenosylmethioninamine:putrescine 3-aminopropyltransferase |
| KEGG:R02869 | 2.5.1.22 | S-adenosylmethioninamine:spermidine 3-aminopropyltransferase |
| KEGG:R03019 | 2.5.1.25 | S-adenosyl-L-methionine:tRNA-uridine 3-(3-amino-3-carboxypropyl)transferase |
| KEGG:R03072 | 2.5.1.38 | S-adenosyl-L-methionine:nocardicin-E 3-amino-3-carboxypropyltransferase |
| KEGG:R03271 | 2.5.1.23 | S-adenosylmethioninamine:propane-1,3-diamine 3-aminopropyltransferase |
| KEGG:R03726 | 2.5.1.24 | S-adenosyl-L-methionine:N6-(delta2-isopentenyl)-adenine 3-(3-amino-3-carboxypropyl)-transferase |
| KEGG:R08359 | 2.5.1.16 | S-adenosylmethioninamine:cadaverine 3-aminopropyltransferase |
| KEGG:R08939 | 2.3.1.184 | butyryl-[acyl-carrier protein]:S-adenosyl-L-methionine butyryltranserase (lactone-forming, methylthioadenosine-releasing) |
| KEGG:R08940 | 2.3.1.184 | acyl-[acyl-carrier protein]:S-adenosyl-L-methionine acyltranserase (lactone-forming, methylthioadenosine-releasing) |
| KEGG:R09072 | S-adenosyl-L-methionine:1,2-diacyl-sn-glycerol 3-amino-3-carboxypropyltransferase | |
| KEGG:R09531 | 2.5.1.79 | S-adenosylmethioninamine:spermidine 3-aminopropyltransferase (thermospermine synthesizing) |
| KEGG:R09660 | 3.5.4.31 | S-methyl-5'-thioadenosine amidohydrolase |
| KEGG:R10338 | 2.5.1.104 | S-adenosyl-3-(methylsulfanyl)propylamine:agmatine 3-aminopropyltransferase |
| KEGG:R10455 | 2.5.1.108 | S-adenosyl-L-methionine:L-histidine-[translation elongation factor 2] 2-[(3S)-3-amino-3-carboxypropyl]transferase |
| KEGG:R10526 | 2.3.1.228 | isovaleryl-CoA:S-adenosyl-L-methionine isovaleryltranserase (lactone-forming, methylthioadenosine-releasing) |
| KEGG:R10529 | 2.3.1.229 | 4-coumaroyl-CoA:S-adenosyl-L-methionine trans-4-coumaroyltranserase (lactone-forming, methylthioadenosine-releasing) |
Taxonomy Source
- Chlamydomonas reinhardtii [ncbi taxid: 3055]
- Escherichia coli [ncbi taxid: 562]
- Glehnia littoralis [ncbi taxid: 48119]
- Homo sapiens [ncbi taxid: 9606]
- Mus musculus [ncbi taxid: 10090]
- Pinellia ternata [ncbi taxid: 199225]
- Saccharomyces cerevisiae [ncbi taxid: 4932]
- Unknown-fungus sp. [ncbi taxid: ]
Pathway Synthetic
| pathway id | name |
|---|---|
| BioCyc:HUMAN_PWY-7286 | 7-(3-amino-3-carboxypropyl)-wyosine biosynthesis |
| BioCyc:HUMAN_BSUBPOLYAMSYN-PWY | spermidine biosynthesis |
| BioCyc:META_BSUBPOLYAMSYN-PWY | spermidine biosynthesis I |
| BioCyc:META_PWY0-1391 | S-methyl-5'-thioadenosine degradation IV |
| BioCyc:META_PWY-6753 | S-methyl-5'-thioadenosine degradation III |
| BioCyc:META_PWY-6756 | S-methyl-5'-thioadenosine degradation II |
| BioCyc:META_PWY-7546 | diphthamide biosynthesis II (eukaryotes) |
| BioCyc:META_PWY-6795 | diacylglyceryl-N,N,N-trimethylhomoserine biosynthesis |
| BioCyc:META_POLYAMINSYN3-PWY | superpathway of polyamine biosynthesis II |
| BioCyc:META_PWY-7527 | L-methionine salvage cycle III |
| BioCyc:META_ETHYL-PWY | ethylene biosynthesis I (plants) |
| BioCyc:ECO_POLYAMSYN-PWY | superpathway of polyamine biosynthesis I |
| BioCyc:YEAST_PWY-7546 | diphthamide biosynthesis |
| BioCyc:YEAST_PWY-7286 | 7-(3-amino-3-carboxypropyl)-wyosine biosynthesis |
| BioCyc:ARA_PWYQT-94 | superpathway of polyamine biosynthesis |
| BioCyc:TRYPANO_ORNSPNANA-PWY | spermine biosynthesis II |
| BioCyc:TRYPANO_BSUBPOLYAMSYN-PWY | spermidine biosynthesis I |
| BioCyc:VCHO_PWY0-1391 | S-methyl-5'-thioadenosine degradation IV |
| BioCyc:PLASMO_PWY0-1303 | aminopropylcadaverine biosynthesis |
| BioCyc:PLASMO_BSUBPOLYAMSYN-PWY | spermidine biosynthesis I |