(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol

• ChemBase ID: 134202
• Molecular Formular: C11H15N5O3S
• Molecular Mass: 297.3335
• Monoisotopic Mass: 297.08956037
• SMILES: CSC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O
• Canonical SMILES: CSC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N
• 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
• InChIKey: WUUGFSXJNOTRMR-IOSLPCCCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
• IUPAC Traditional name: methylthioadenosine
• Synonyms: MTA; Methylthioadenosine; 5′-Deoxy-5′-(methylthio)adenosine; 5'-S-Methylthioadenosine; NSC 335422; Vitamin L2; 1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-β-D-ribofuranose; 5'-Deoxy-5'-(methylthio)adenosine; 5'-S-Methyl-5'-thioadenosine; 5'-(Methylthio)-5'-deoxyadenosine; 5'-(Methylthio)adenosine; 5'-Deoxy(methylthio)adenosine; 5'-Methylthioadenosine; 5'-S-Methyl-5'-thioadenosine

Database IDs

• CAS Number: 2457-80-9
• MDL Number: MFCD00010533
• Beilstein Number: 42420
• PubChem SID: 162228479; 24893915
• PubChem CID: 439176

CALCULATED PROPERTIES

• Acid pKa: 12.471831
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.72364795
• LogD (pH = 7.4): -0.61015856
• Log P: -0.60849273
• Molar Refractivity: 74.0292 cm^3
• Polarizability: 28.74894 Å^3
• Polar Surface Area: 119.31 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• RTECS: AU7410000
• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... ADORA2B(136), ADORA3(140)mouse ... Mtap(66902)rat ... Adora1(29290), Adora2a(25369)

DETAILS

Sigma Aldrich - D5011

Application
5′-Deoxy-5′-(methylthio)adenosine (Methylthioadenosine) may be used as a substrate to study the specificity and kinetics of 5′-methylthioadenosinephosphorylase (MTAP) (EC2.4.2.28), a tumor suppressor gene expressed enzyme that supports the S-adenosylmethionine (AdoMet) and methionine salvage pathways. Methylthioadenosine is used in studies on bacterial quorum sensing pathways that envolve enzymes such as 5′-Methylthioadenosine/S-adenosylhomocysteine nucleosidase (MTAN).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D5011.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - D242600

5′-Deoxy-5′-(methylthio)adenosine (Methylthioadenosine) may be used as a substrate to study the specificity and kinetics of 5′-methylthioadenosinephosphorylase (MTAP) (EC2.4.2.28), a tumor suppressor gene expressed enzyme that supports the S-adenosylmethi

REFERENCES

• Pegg, A., et al.: Biochem. J., 115, 241 (1969)
• Olopade, O., et al.: Cancer Res., 53, 2410 (1969)
• Hartmann, S., et al.: Clin. Chem., 52, 1127 (1969)
• Penner, N., et al.: J. Pharm. Biomed. Anal., 52, 534 (1969)