5'-Methylthioadenosine

Details

• Internal ID: ed4a7fac-a28a-4167-8d6e-b09a3080cbd2
• Taxonomy: Nucleosides, nucleotides, and analogues > 5-deoxyribonucleosides > 5-deoxy-5-thionucleosides
• IUPAC Name: (2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
• InChI: 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
• Popularity: 758 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₅N₅O₃S
• Molecular Weight: 297.34 g/mol
• Exact Mass: 297.08956053 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: -0.30

Synonyms

• 5'-methylthioadenosine
• 5'-S-methyl-5'-thioadenosine
• 5'-Deoxy-5'-(methylthio)adenosine
• 5'-DEOXY-5'-METHYLTHIOADENOSINE
• 5'-(Methylthio)adenosine
• S-methyl-5'-thioadenosine
• 5'-S-Methylthioadenosine
• Vitamin L(sub 2)
• 5'-Deoxy(methylthio)adenosine
• NSC 335422
• UNII-634Z2VK3UQ
• CHEBI:17509
• 5'-S-methyl-5'-thio-Adenosine
• 5-Methyl-Thioadenosine
• DTXSID20179308
• S-methyl-5-thioadenosine
• BRN 0042420
• 4-26-00-03675 (Beilstein Handbook Reference)
• (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
• NSC-335422
• 1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-D-Ribofuranose
• 1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-delta-Ribofuranose
• 7-(TETRAHYDRO-3,4-DIHYDROXY-5-(METHYLMERCAPTOMETHYL)-2-FURYL)ADENINE
• 5-MTDA
• 5'-methylthio-5'-deoxyadenosine
• (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-((methylsulfanyl)methyl)oxolane-3,4-diol
• RefChem:100831
• adenine(5'-deoxy-5'-methylthio)9-beta-D-furanoriboside
• DTXCID10101799
• METHYLTHIOADENOSINE [INCI]
• 5'-Deoxy-5'-(methylsulphanyl)adenosine
• 9-(5-S-Methyl-5-thio-b-D-ribofuranosyl)-9H-purin-6-amine
• 9-(5-S-Methyl-5-thio-I2-D-ribofuranosyl)-9H-purin-6-amine
• 57301-10-7
• 626-314-3
• WUUGFSXJNOTRMR-IOSLPCCCSA-N
• 2457-80-9
• ADENOSINE, 5'-S-METHYL-5'-THIO-
• 5-Methylthioadenosine
• (2R,3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diol
• Vitamin L2
• Thiomethyladenosine
• MTA
• 5'-(Methylthio)-5'-deoxyadenosine
• MFCD00010533
• C11H15N5O3S
• (2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
• 634Z2VK3UQ
• CHEMBL277041
• 5'-CH3S-5'dA
• 5'-deoxy-5'-(methylsulfanyl)adenosine
• 9-(5-S-methyl-5-thio-beta-D-ribofuranosyl)-9H-purin-6-amine
• (2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)tetrahydrofuran-3,4-diol
• .beta.-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-
• 5'-Thiomethyladenosine
• Adenosine, 5-methylthio-
• MTA; 5'-Methylthioadenosine
• SCHEMBL160358
• SCHEMBL536062
• orb1299106
• 5-Deoxy-5-Methylthio adenosine
• SCHEMBL29361072
• BDBM22111
• MSK6925
• 5'-Deoxy-5'-methylthio-adenosine
• AIDS003668
• EX-A4640
• PDSP1_001005
• PDSP2_000989
• AKOS016006238
• DB02282
• DS-4224
• ND07992
• 5 inverted exclamation marka-Deoxy-5 inverted exclamation marka-(methylthio)adenosine
• 5'-Deoxy-5'-(methylthio)-D-adenosine
• HY-16938
• SY288175
• CS-0012983
• NS00014568
• C00170
• C74264
• F230436
• Q3599216
• 5'-Deoxy-5'-methylthioadenosine - CAS 2457-80-9
• 7DDC4B4A-0E54-449C-A502-BDAEA990DE4C
• Z2217101605
• Adenosine, 5'-S-methyl-5'-thio- (6CI,7CI,8CI,9CI)
• 5'-Deoxy-5'-(methylthio)-D-adenosine;5'-(Methylthio)-5'-deoxyadenosine
• (2R,3R,4S,5R)-2-(6-Aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
• (2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
• 5 inverted exclamation mark -Deoxy-5 inverted exclamation mark -(methylthio)adenosine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL255	P29275	Adenosine A2b receptor	8200 nM; 13900 nM	Ki; Ki	PMID: 15084123; PMID: 15084123
CHEMBL256	P0DMS8	Adenosine A3 receptor	71000 nM	IC50	PMID: 15084123

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.67%	96.09%
CHEMBL3589	P55263	Adenosine kinase	94.66%	98.05%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	94.44%	100.00%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	91.07%	80.33%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	91.01%	96.67%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	90.09%	95.48%
CHEMBL226	P30542	Adenosine A1 receptor	88.36%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.99%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	87.49%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.15%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.90%	95.89%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	80.88%	98.46%
CHEMBL4040	P28482	MAP kinase ERK2	80.72%	83.82%
CHEMBL2581	P07339	Cathepsin D	80.71%	98.95%

Plants that contains it

• Ephedra distachya
• Euphorbia tithymaloides
• Glehnia littoralis
• Hyacinthoides non-scripta
• Pinellia ternata

Cross-Links

• PubChem: 439176
• NPASS: NPC136349
• ChEMBL: CHEMBL277041
• LOTUS: LTS0058305
• wikiData: Q3599216