5'-Methylthioadenosine
Basic information
- CAS
2457-80-9- Standard SMILES
CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O- InChIKey
WUUGFSXJNOTRMR-IOSLPCCCSA-N- Molecular formula
- C11H15N5O3S
- Average molar mass
- 297.34 g/mol
- Monoisotopic mass
- 297.08956053
Overview
5'-S-methyl-5'-thioadenosine is adenosine with the hydroxy group at C-5' substituted with a methylthio (methylsulfanyl) group. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a human metabolite and an algal metabolite. It is functionally related to an adenosine.
Names & identifiers
- Preferred name
- 5'-Methylthioadenosine
- IUPAC
- (2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
- English name
- 5'-Deoxy-5'-methylthioadenosine
- Molecular formula
- C11H15N5O3S
- Molecular weight
- 297.33
Names & synonyms
Methylthioadenosine5'-methylthioadenosine5'-S-methyl-5'-thioadenosine5'-Deoxy-5'-(methylthio)adenosine5'-DEOXY-5'-METHYLTHIOADENOSINE5'-(Methylthio)adenosineS-methyl-5'-thioadenosine5'-S-MethylthioadenosineVitamin L(sub 2)5'-Deoxy(methylthio)adenosineNSC 335422UNII-634Z2VK3UQ
Show more names
MTAAdenylthiomethylpentose(2R,3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diolMESADO5’-methylthioadenosineAdenosyl Methionine Impurity 1beta-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-
5'-S-methyl-5'-thio-AdenosineDTXSID20179308S-methyl-5-thioadenosine(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diolBRN 0042420CHEBI:175094-26-00-03675 (Beilstein Handbook Reference)NSC-335422
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 145 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 3
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 352
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physical DescriptionSolid
Collision Cross Section
162.5 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
167 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
170.34 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
170.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
168.3 Ų [M-H]-
Physicochemical properties
- Melting point
- 210 · 210-213 °C (dec.)
- Boiling point
- 642.7 · 642.7±65.0 °C(Predicted)
- Density
- 1.85 · 1.85±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- DMF (Sparingly), DMSO (Slightly), Methanol (Slightly)
- form
- White solid
- pka
- 13.1 · 13.10±0.70(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- F
- 10-21
- wgk
- 3
- rtecs
- AU7410000
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585)
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Tissue LocationsFibroblasts
Cellular LocationsCytoplasm
Metabolite PathwaysCystathionine Beta-Synthase Deficiency
Applications
Uses5′-Deoxy-5′-(methylthio)adenosine has been used as a protein methylation inhibitor to reduce E2F transcription factor 1 (E2F1) protein abundance in hepatocellular carcinoma (HCC) cells. It has also been used to inhibit histone methylation modification and study its role in hypoxia inducible factor-1 (Hif-1) nuclear transport.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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