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

• ChemBase ID: 134153
• Molecular Formular: C15H23ClN6O5S
• Molecular Mass: 434.89832
• Monoisotopic Mass: 434.11391655
• SMILES: C[S+](CC[C@@H](C(=O)O)N)C[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O.[Cl-]
• Canonical SMILES: C[S+](C[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)CC[C@@H](C(=O)O)N.[Cl-]
• InChI: InChI=1S/C15H22N6O5S.ClH/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;/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25);1H/t7-,8+,10+,11+,14+,27?;/m0./s1
• InChIKey: DYFPQIYEZQULMZ-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 chloride
• IUPAC Traditional name: SAMe chloride
• Synonyms: Active methionine; AdoMet; SAM chloride dihydrochloride; S-(5′-Adenosyl)-L-methionine chloride dihydrochloride; 5'-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5'-deoxyadenosine Disulfate; 5'-[(L-3-Amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine Disulfate; S-Adenosylmethionine Disulfate; Active Methionine Disulfate; Ademetionine Disulfate; L-S-Adenosylmethionin Disulfate; S-Adenosyl-L-methionine Disulfate; S-(5'-Adenosyl)-L-methionine Disulfate Salt (Synthetic)(Mixture of Diastereomers)

Database IDs

• CAS Number: 86867-01-8
• EC Number: 246-184-8
• MDL Number: MFCD22571809
• Beilstein Number: 6560002
• PubChem SID: 24891164; 162228430
• PubChem CID: 90473

CALCULATED PROPERTIES

• Acid pKa: 1.7050823
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -5.2821784
• 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
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble100 mg/mL; Methanol; Water
• Apperance: Light Beige to Pale Brown Solid
• Melting Point: 121-125°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥80%
• Biological Source: from yeast (L-Methionine enriched)
• Shipped in: dry ice

DETAILS

Sigma Aldrich - A7007

Analysis Note
Purity based on UV and HPLC.
Caution
This material is 80-90% pure when prepared, but is very unstable. As much as 10% purity loss per day at 25 °C has been noted.
Biochem/physiol Actions
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.

Toronto Research Chemicals - A291530

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

REFERENCES

• Friedel, H., et al.: Drugs, 38, 389 (1989)
• Lu, S., et al.: Int. J. Biochem. Cell Biol., 32, 391 (1989)
• Amin, K., et al.: Pharm. Res., 18, 914 (1989)