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

• ChemBase ID: 175140
• Molecular Formular: C13H16F3NO9S
• Molecular Mass: 419.3276496
• Monoisotopic Mass: 419.04978676
• SMILES: [C@@H]1([C@H]([C@@H](O[C@@H]1CO)[n+]1cc(ccc1)C(=O)OC)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)OC
• InChI: InChI=1S/C12H16NO6.CHF3O3S/c1-18-12(17)7-3-2-4-13(5-7)11-10(16)9(15)8(6-14)19-11;2-1(3,4)8(5,6)7/h2-5,8-11,14-16H,6H2,1H3;(H,5,6,7)/q+1;/p-1/t8-,9-,10-,11-;/m1./s1
• InChIKey: VIOOBHRPBYGYGY-PSQZEURLSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-(methoxycarbonyl)(^2H₄)-1λ^5-pyridin-1-ylium trifluoromethanesulfonate
• IUPAC Traditional name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-(methoxycarbonyl)(^2H₄)-1λ^5-pyridin-1-ylium triflate
• Synonyms: 3-(Methoxycarbonyl)-1-β-D-ribofuranosyl-pyridinium-d4; Nicotinic Acid Riboside-d4 Methyl Ester Triflate

Database IDs

• PubChem SID: 164231050
• PubChem CID: 71751029

CALCULATED PROPERTIES

• Acid pKa: 11.722088
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.967945
• LogD (pH = 7.4): -4.9679246
• Log P: -4.967945
• Molar Refractivity: 63.7814 cm^3
• Polarizability: 25.31552 Å^3
• Polar Surface Area: 100.1 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Yellow Syrup

DETAILS

Toronto Research Chemicals - N429407

The labelled analogue of an effective agent for increasing nicotinamide adenine dinucleotide (NAD) concentrations in mammalian cells.

REFERENCES

• Belenky, P. et al.; J. Biol. Chem. 284, 158 (2009)
• Yang, T. et al.: J. Med. Chem., 50, 6458 (2009)