3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl](2H4)-1λ5-pyridin-1-ylium trifluoromethanesulfonate

• ChemBase ID: 175101
• Molecular Formular: C12H15F3N2O8S
• Molecular Mass: 404.3163096
• Monoisotopic Mass: 404.05012111
• SMILES: [C@@H]1([C@H]([C@@H](O[C@@H]1CO)[n+]1cc(ccc1)C(=O)N)O)O.C(F)(F)(F)S(=O)(=O)[O-]
• Canonical SMILES: [O-]S(=O)(=O)C(F)(F)F.OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)[n+]1cccc(c1)C(=O)N
• InChI: InChI=1S/C11H14N2O5.CHF3O3S/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11;2-1(3,4)8(5,6)7/h1-4,7-9,11,14-16H,5H2,(H-,12,17);(H,5,6,7)/t7-,8-,9-,11-;/m1./s1
• InChIKey: ZEWRNTDQENDMQK-IVOJBTPCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl](^2H₄)-1λ^5-pyridin-1-ylium trifluoromethanesulfonate
• IUPAC Traditional name: 3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl](^2H₄)-1λ^5-pyridin-1-ylium triflate
• Synonyms: 3-(Aminocarbonyl)-1-β-D-ribofuranosylpyridinium-d4 Trifluoromethanesulfonic Acid Salt; Nicotinamide-d4 Ribose Triflate; Nicotinamide-d4 Ribonucleoside Triflate; β-NAR-d4; Ribosylnicotinamide-d4 Triflate; Nicotinamide Riboside-d4 Triflate (d3-Major)α/β mixture

Database IDs

• PubChem SID: 164231011
• PubChem CID: 71751001

CALCULATED PROPERTIES

• Acid pKa: 11.390918
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -6.1207814
• LogD (pH = 7.4): -6.12074
• Log P: -6.120782
• Molar Refractivity: 60.8345 cm^3
• Polarizability: 23.731005 Å^3
• Polar Surface Area: 116.89 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale Yellow Gel

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - N407772

Labelled Nicotinamide (N407750) analog. Nicotinamide riboside (β-NAR) is an intermediate in one biosynthetic pathway by which Nicotamide is converted into NAD (Nicotinamide Adenine Dinucleotide)

REFERENCES

• Friedlos, F., et al.: J. Biochem. Pharmacol., 44, 25 (1992)
• Ong, S., et al.: Biochemistry, 11210 (1992)
• Zhang, X., et al.: J. Biol. Chem., 278, 13503 (1992)