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

• ChemBase ID: 175138
• Molecular Formular: C11H13NO6
• Molecular Mass: 255.22402
• Monoisotopic Mass: 255.07428714
• SMILES: [C@@H]1([C@H]([C@@H](O[C@@H]1CO)[n+]1cc(ccc1)C(=O)[O-])O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)[n+]1cccc(c1)C(=O)[O-]
• InChI: InChI=1S/C11H13NO6/c13-5-7-8(14)9(15)10(18-7)12-3-1-2-6(4-12)11(16)17/h1-4,7-10,13-15H,5H2/t7-,8-,9-,10-/m1/s1
• InChIKey: PUEDDPCUCPRQNY-ZYUZMQFOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl](^2H₄)-1λ^5-pyridin-1-ylium-3-carboxylate
• IUPAC Traditional name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl](^2H₄)-1λ^5-pyridin-1-ylium-3-carboxylate
• Synonyms: 3-Carboxy-1-β-D-ribofuranosylpyridinium-d4 Inner Salt; 3-Carboxy-1-β-D-ribofuranosylpyridinium-d4 Hydroxide Inner Salt; Nicotinic Acid-d4 Ribonucleoside; Nicotinic-d4 Riboside; Nicotinic Acid-d4 Riboside

Database IDs

• PubChem SID: 164231048
• PubChem CID: 71751026

CALCULATED PROPERTIES

• Acid pKa: 2.7579036
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -5.542761
• LogD (pH = 7.4): -5.5433207
• Log P: -5.3138394
• Molar Refractivity: 69.8494 cm^3
• Polarizability: 23.16659 Å^3
• Polar Surface Area: 113.93 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 142-144°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N429402

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

REFERENCES

• Yang, T. et al.: J. Med. Chem., 50, 6458 (2007)