[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})(2H3)methylsulfanium hydrogen sulfate

• ChemBase ID: 159574
• Molecular Formular: C15H24N6O9S2
• Molecular Mass: 496.51586
• Monoisotopic Mass: 496.10461838
• SMILES: n1cnc2c(c1N)ncn2[C@H]1[C@@H]([C@@H]([C@H](O1)C[S+](CC[C@H](N)C(=O)O)C)O)O.S(=O)(=O)(O)[O-]
• Canonical SMILES: [O-]S(=O)(=O)O.C[S+](C[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C15H22N6O5S.H2O4S/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;1-5(2,3)4/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25);(H2,1,2,3,4)/t7-,8+,10+,11+,14+,27?;/m0./s1
• InChIKey: XANXGSJDYUBBIT-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})(^2H₃)methylsulfanium hydrogen sulfate
• IUPAC Traditional name: [(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})(^2H₃)methylsulfanium hydrogensulfate
• Synonyms: L-S-Adenosylmethionin-d3 Disulfate; S-Adenosyl-L-methionine-d3 Disulfate; S-(5'-Adenosyl)-L-methionine-d3 Disulfate Salt (Synthetic)(Mixture of Diastereomers); 5'-[[(3S)-3-Amino-3-carboxypropyl](methyl-d3)sulfonio]-5'-deoxyadenosine Disulfate; 5'-[(L-3-Amino-3-carboxypropyl)(methyl-d3)sulfonio]-5'-deoxyadenosine Disulfate; S-Adenosylmethionine-d3 Disulfate; Active Methionine-d3 Disulfate; Ademetionine-d3 Disulfate

Database IDs

• PubChem SID: 162253709
• PubChem CID: 71313044

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 - A291532

Labelled S-(5'-Adenosyl)-L-methionine. 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 m

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)