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

• ChemBase编号: 134202
• 分子式: C11H15N5O3S
• 平均质量: 297.3335
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
• IUPAC传统名: methylthioadenosine
• 别名: 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

登记号

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

理论计算性质

• Acid pKa: 12.471831
• 质子受体: 7
• 质子供体: 3
• LogD (pH = 5.5): -0.72364795
• LogD (pH = 7.4): -0.61015856
• Log P: -0.60849273
• 摩尔折射率: 74.0292 cm^3
• 极化性: 28.74894 Å^3
• 极化表面积: 119.31 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: Powder

安全信息

• RTECS编号: AU7410000
• 德国WGK号: 3
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... ADORA2B(136), ADORA3(140)mouse ... Mtap(66902)rat ... Adora1(29290), Adora2a(25369)

详细说明

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

参考文献

• 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)