[(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 ID: 133635
• Molecular Formular: C22H30N6O8S2
• Molecular Mass: 570.639
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: [(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 Traditional name: SAMe tosylate
• Synonyms: AdoMet; SAM p-toluenesulfonate salt; S-(5′-Adenosyl)-L-methionine p-toluenesulfonate salt; 5'-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5'-deoxy-Adenosine tosylate

Database IDs

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

CALCULATED PROPERTIES

• Rotatable Bonds: 8
• Lipinski's Rule of Five: false
• Acid pKa: 1.7050833
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -5.2821803
• LogD (pH = 7.4): -5.3258553
• Log P: -5.3224516
• Molar Refractivity: 96.2349 cm^3
• Polarizability: 38.568764 Å^3
• Polar Surface Area: 182.63 Å^2

PROPERTIES

Physical Property

• Solubility: H2O: soluble100 mg/mL

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥80% (HPLC); ≥80% (spectrophotometric assay); 95%
• Compostion: p-Toluenesulfonate content, 1.6-4.4 mol/mol
• Biological Source: from yeast (L-methionine enriched)
• Shipped in: dry ice

DETAILS

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.