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

Reviewed

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.

Entity Information

DBLinks

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

Metabolic Network
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)
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Organism Source

Taxonomy Source

  1. Chlamydomonas reinhardtii [ncbi taxid: 3055]
  2. Escherichia coli [ncbi taxid: 562]
  3. Glehnia littoralis [ncbi taxid: 48119]
  4. Homo sapiens [ncbi taxid: 9606]
  5. Mus musculus [ncbi taxid: 10090]
  6. Pinellia ternata [ncbi taxid: 199225]
  7. Saccharomyces cerevisiae [ncbi taxid: 4932]
  8. 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
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