Adenylthiomethylpentose

Names

[ Name ]:
Adenylthiomethylpentose

[Synonym ]:
5-Methylthioadenosine
1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-β-D-Ribofuranose
β-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-
Vitamin L2
5'-S-Methylthioadenosine
(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
5'-S-Methyl-5'-thioadenosine
7-[Tetrahydro-3,4-dihydroxy-5-(methylmeracptomrthyl)-2-futyl]adenine
Adenosine, 5'-S-methyl-5'-thio-
5'-Deoxy-5'-(methylthio)adenosine
MFCD00010533
MTA,Methylthioadenosine
5'-Deoxy-5'-Methylthioadenosine
Adenylthiomethylpentose
(2R,3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diol

Biological Activity

[Description]:

5'-Methylthioadenosine is produced from S-adenosylmethionine and behaves as a powful inhibitory product.

[Related Catalog]:

Research Areas >> Metabolic Disease

Natural Products >> Others

[Target]

Human Endogenous Metabolite

[In Vitro]

5'-Methylthioadenosine (MTA) can affect cellular processes in many ways. 5'-Methylthioadenosine has been shown to influence numerous critical responses of the cell including regulation of gene expression, proliferation, differentiation and apoptosis. Although most of these responses have been observed at the pharmacological level, their specificity makes it tempting to speculate that endogenous 5'-Methylthioadenosine could play a regulatory role in the cell. Finally, observations carried out in models of liver damage and cancer demonstrate a therapeutic potential for 5'-Methylthioadenosine that deserves further consideration[1].

[References]

[1]. Avila MA, et al. Methylthioadenosine. Int J Biochem Cell Biol. 2004 Nov;36(11):2125-30.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
642.7±65.0 °C at 760 mmHg

[ Melting Point ]:
210-213ºC (dec.)

[ Molecular Formula ]:
C₁₁H₁₅N₅O₃S

[ Molecular Weight ]:
297.333

[ Flash Point ]:
342.5±34.3 °C

[ Exact Mass ]:
297.089569

[ PSA ]:
144.61000

[ LogP ]:
0.67

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.843

[ Storage condition ]:
−20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AU7410000

CHEMICAL NAME :: Adenosine, 5'-S-methyl-5'-thio-

CAS REGISTRY NUMBER :: 2457-80-9

BEILSTEIN REFERENCE NO. :: 0042420

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C11-H15-N5-O3-S

MOLECULAR WEIGHT :: 297.37

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - rat Liver

DOSE/DURATION :: 100 umol/L

REFERENCE :: CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 8,653,1987

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
AU7410000

[ HS Code ]:
2934999090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Related Compounds

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