MiMeDB: Showing metabocard for 5'-Methylthioadenosine (MMDBc0000563)

Microbial

Plant

Animal

Pharmaceutical

Xenobiotic

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:37 UTC

Update Date

2024-10-13 06:56:09 UTC

Metabolite ID

MMDBc0000563

Metabolite Identification

Common 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 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

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₁₁H₁₅N₅O₃S

Average Mass

297.334

Monoisotopic Mass

297.089560061

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not 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 Key

WUUGFSXJNOTRMR-IOSLPCCCSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Fibroblasts
Placenta
Platelet
Prostate
Urine

Tissue Locations

Fibroblasts
Placenta
Platelet
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191887	Spermine synthase	Enzyme	P52788	Homo sapiens
MMDBp0191888	Spermidine synthase	Enzyme	P19623	Homo sapiens
MMDBp0192064	S-methyl-5'-thioadenosine phosphorylase	Enzyme	Q13126	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019225	Cadaverine	5'-Methylthioadenosine	Polyamine aminopropyltransferase	Synthesis	PathBank	31602464
MMDBr0019227	Putrescine	Spermidine	Polyamine aminopropyltransferase	Synthesis	PathBank	31602464
MMDBr0019425	Putrescine	Spermidine	Spermidine synthase SPE3	Synthesis	PathBank	31602464
MMDBr0019428	Spermidine	Spermine	Spermine synthase SPE4	Synthesis	PathBank	31602464
MMDBr0024341	S-Adenosylmethionine	5'-Methylthioadenosine	Acyl-homoserine-lactone synthase	Synthesis	RHEA	34755880
MMDBr0024413	S-Adenosylmethionine	5'-Methylthioadenosine	tRNA-uridine aminocarboxypropyltransferase	Transfer of a tRNA-uridine aminocarboxypropyl group	RHEA	34755880
MMDBr0024955	S-Adenosylmethionine	5'-Methylthioadenosine	tRNA(Phe) (4-demethylwyosine(37)-C(7)) aminocarboxypropyltransferase	Synthesis	RHEA	34755880
MMDBr0024965	L-Histidine	5'-Methylthioadenosine	2-(3-amino-3-carboxypropyl)histidine synthase	Synthesis	RHEA	34755880
MMDBr0025803	S-Adenosylmethionine	5'-Methylthioadenosine	16S rRNA aminocarboxypropyltransferase	Transfer of an aminocarboxypropyl group	RHEA	34755880
MMDBr0025804	S-Adenosylmethionine	5'-Methylthioadenosine	18S rRNA aminocarboxypropyltransferase	Transfer of an aminocarboxypropyl group	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Bacteroidetes	100	Human feces; Human stool; Human ; Human saliva; Human gastric fluid; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	429	Human stool; Human ; Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Catfish	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	340	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Lion ; Cattle ; River trout ; Human subgingival plaque; Chicken ; Sheep	Metabolic reconstruction
Bacteria	Actinobacteria	12	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	112	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	29	Human stool; Human ; Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Catfish	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	7	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	21	Human feces; Human	Metabolic reconstruction
Bacteria	Proteobacteria	13	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Lion ; Cattle ; River trout ; Human subgingival plaque; Chicken ; Sheep	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	3	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Archaea/Archaea	Crenarchaeota	16		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	14	Human feces; Human saliva	Unknown
Bacteria/Eubacteria	Chloroflexi	1
Eukaryota/Fungi	Basidiomycota	4
Bacteria/Eubacteria	Cyanobacteria	19
Bacteria/Eubacteria	Acidobacteria	1
Archaea/Archaea	Thaumarchaeota	2		Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	30		Metabolic reconstruction
Bacteria	nah	3
Bacteria/Eubacteria	Aquificae	2
Bacteria/Eubacteria	Deinococcus-thermus	4
Archaea/Archaea	Korarchaeota	1
Bacteria/Eubacteria	Thermotogae	3
Viruses	Uroviricota	1
Bacteria/Eubacteria	Dictyoglomi	2
Bacteria/Eubacteria	Nitrospirae	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Urine	Detected and Quantified	0.12	0.05	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	9129323
Human Urine	Detected and Quantified	0.12	0.08	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	9129323
Human Urine	Detected and Quantified	0.13	0.11	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	9129323
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Blood	Detected but not Quantified							HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Mills GC, Mills JS: Urinary excretion of methylthioadenosine in immunodeficient children. Clin Chim Acta. 1985 Mar 30;147(1):15-23. doi: 10.1016/0009-8981(85)90005-1. [PubMed:3987052 ]
Mills GC, Schmalstieg FC, Goldblum RM: Urinary excretion of modified purines and nucleosides in immunodeficient children. Biochem Med. 1985 Aug;34(1):37-51. doi: 10.1016/0006-2944(85)90060-2. [PubMed:4052062 ]
Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. doi: 10.1016/s0021-9673(96)00757-1. [PubMed:9129323 ]
Gerasimovskaya EV, Ahmad S, White CW, Jones PL, Carpenter TC, Stenmark KR: Extracellular ATP is an autocrine/paracrine regulator of hypoxia-induced adventitial fibroblast growth. Signaling through extracellular signal-regulated kinase-1/2 and the Egr-1 transcription factor. J Biol Chem. 2002 Nov 22;277(47):44638-50. doi: 10.1074/jbc.M203012200. Epub 2002 Sep 18. [PubMed:12244041 ]
Contreres JO, Dupuy E, Job B, Habib A, Bryckaert M, Rosa JP, Simoneau G, Herbert JM, Savi P, Levy-Toledano S: Effect of clopidogrel administration to healthy volunteers on platelet phosphorylation events triggered by ADP. Br J Haematol. 2003 Feb;120(4):633-42. doi: 10.1046/j.1365-2141.2003.04166.x. [PubMed:12588350 ]
Avila MA, Garcia-Trevijano ER, Lu SC, Corrales FJ, Mato JM: Methylthioadenosine. Int J Biochem Cell Biol. 2004 Nov;36(11):2125-30. doi: 10.1016/j.biocel.2003.11.016. [PubMed:15313459 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for 5'-Methylthioadenosine (MMDBc0000563)

MOL for #<Metabolite:0x00007fe748a3fa48>

3D MOL for #<Metabolite:0x00007fe748a3fa48>

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PDB for #<Metabolite:0x00007fe748a3fa48>

3D PDB for #<Metabolite:0x00007fe748a3fa48>

SMILES for #<Metabolite:0x00007fe748a3fa48>

INCHI for #<Metabolite:0x00007fe748a3fa48>

Structure for #<Metabolite:0x00007fe748a3fa48>

3D Structure for #<Metabolite:0x00007fe748a3fa48>