[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy(2,3,4,5-13C4)oxolan-2-yl](13C)methyl})methylsulfanium chloride

• ChemBase ID: 159575
• Molecular Formular: C15H23ClN6O5S
• Molecular Mass: 439.86159419
• Monoisotopic Mass: 439.13069074
• SMILES: n1cnc2c(c1N)ncn2[13C@H]1[13C@@H]([13C@@H]([13C@H](O1)[13CH2][S+](CC[C@H](N)C(=O)O)C)O)O.[Cl-]
• Canonical SMILES: C[S+]([13CH2][13C@H]1O[13C@H]([13C@@H]([13C@@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/i4+1,8+1,10+1,11+1,14+1
• InChIKey: DYFPQIYEZQULMZ-AITGAKOASA-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-dihydroxy(2,3,4,5-^1^3C₄)oxolan-2-yl](^1^3C)methyl})methylsulfanium chloride
• IUPAC Traditional name: [(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy(2,3,4,5-^1^3C₄)oxolan-2-yl](^1^3C)methyl})methylsulfanium chloride
• Synonyms: 5'-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5'-deoxyadenosine-13C5 Chloride; 5'-[(L-3-Amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine-13C5 Chloride; S-Adenosylmethionine-13C5 Chloride; Active Methionine-13C5 Chloride; Ademetionine-13C5 Chloride; L-S-Adenosylmethionin-13C5 Chloride; S-Adenosyl-L-methionine-13C5 Chloride; S-(5'-Adenosyl)-L-methionine-13C5 Chloride

Database IDs

• PubChem SID: 162253710
• PubChem CID: 71313046

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

DETAILS

Toronto Research Chemicals - A291533

Labelled S-(5'-Adenosyl)-L-methionine Chloride (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

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)