[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium 4-methylbenzene-1-sulfonate

• ChemBase编号: 133635
• 分子式: C22H30N6O8S2
• 平均质量: 570.639
• 单一同位素质量: 570.15665395
• SMILES: Cc1ccc(cc1)S(=O)(=O)[O-].C[S+](CC[C@@H](C(=O)O)N)C[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O
• Canonical SMILES: C[S+](C[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)CC[C@@H](C(=O)O)N.Cc1ccc(cc1)S(=O)(=O)[O-]
• InChI: InChI=1S/C15H22N6O5S.C7H8O3S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21;1-6-2-4-7(5-3-6)11(8,9)10/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25);2-5H,1H3,(H,8,9,10)/t7-,8+,10+,11+,14+,27?;/m0./s1
• InChIKey: VHPOFDUCFKOUHV-XKGORWRGSA-N

名称和登记号

名称

• IUPAC标准名: [(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium 4-methylbenzene-1-sulfonate
• IUPAC传统名: SAMe tosylate
• 别名: AdoMet; SAM p-toluenesulfonate salt; S-(5′-Adenosyl)-L-methionine p-toluenesulfonate salt; 5'-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5'-deoxy-Adenosine tosylate

登记号

• CAS号: 52248-03-0; 17176-17-9
• MDL号: MFCD00063498
• PubChem SID: 24890653; 162227912
• PubChem CID: 10153079

理论计算性质

• 可自由旋转的化学键: 8
• 里宾斯基五规则: false
• Acid pKa: 1.7050833
• 质子受体: 10
• 质子供体: 5
• LogD (pH = 5.5): -5.2821803
• LogD (pH = 7.4): -5.3258553
• Log P: -5.3224516
• 摩尔折射率: 96.2349 cm^3
• 极化性: 38.568764 Å^3
• 极化表面积: 182.63 Å^2

分子性质

理化性质

• 溶解度: H2O: soluble100 mg/mL

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 纯度: ≥80% (HPLC); ≥80% (spectrophotometric assay); 95%
• 主要成分: p-Toluenesulfonate content, 1.6-4.4 mol/mol
• 生物来源: from yeast (L-methionine enriched)
• 运输包装: dry ice

详细说明

Sigma Aldrich - A2408

Biochem/physiol Actions
S-(5′-Adenosyl)-L-methionine (SAM) is anti-apoptotic in normal hepatocytes and normal colon epithelial cells but pro-apoptotic in liver human hepatocellular carcinoma (HCC), HepG2 cells and colon cancer cells.
Methyl donor; cofactor for enzyme-catalyzed methylations, including catechol O-methyltransferase (COMT) and DNA methyltransferases (DNMT). Although present in all cells, it is concentrated in liver where 85% of all methylation reactions occur. It is also involved in regulating liver function, growth, and response to injury.
Caution
This material is unstable at room temperature.