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

• ChemBase ID: 175137
• 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]-1λ^5-pyridin-1-ylium-3-carboxylate
• IUPAC Traditional name: D-ribosylnicotinate
• Synonyms: 3-Carboxy-1-β-D-ribofuranosylpyridinium Inner Salt; 3-Carboxy-1-β-D-ribofuranosyl-pyridinium Hydroxide Inner Salt; Nicotinic Acid Ribonucleoside; Nicotinic Riboside; Nicotinic Acid Riboside

Database IDs

• CAS Number: 17720-18-2
• PubChem SID: 164231047
• PubChem CID: 161233

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: 23.13474 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: 133-138°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - N429400

An effective agent for increasing nicotinamide adenine dinucleotide (NAD) concentrations in mammalian cells.

REFERENCES

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