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

• ChemBase ID: 132357
• Molecular Formular: C15H23IN6O5S
• Molecular Mass: 526.34979
• Monoisotopic Mass: 526.04953687
• SMILES: C[S+](CC[C@@H](C(=O)O)N)C[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O.[I-]
• Canonical SMILES: C[S+](C[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)CC[C@@H](C(=O)O)N.[I-]
• InChI: InChI=1S/C15H22N6O5S.HI/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: XQMWYLXPEGFCFT-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 iodide
• IUPAC Traditional name: SAMe iodide
• Synonyms: AdoMet; SAM; S-(5′-Adenosyl)-L-methionine iodide

Database IDs

• CAS Number: 3493-13-8
• EC Number: 222-486-5
• MDL Number: MFCD00043192
• Beilstein Number: 4120787
• PubChem SID: 24890852; 162226634
• PubChem CID: 10143006

CALCULATED PROPERTIES

• 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
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble100 mg/mL

Safety Information

• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥80% (HPLC); ≥80% (spectrophotometric assay)
• Biological Source: from yeast
• Shipped in: dry ice

DETAILS

Sigma Aldrich - A4377

Analysis Note
Purity based on UV and HPLC.
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.
Caution
This material is very unstable at room temperature.