1-[(2R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)(13C)methyl](2,3,4,5-13C4)oxolan-2-yl]-1λ5-pyridin-1-ylium-3-carboxylate

• ChemBase ID: 175136
• Molecular Formular: C11H14NO9P
• Molecular Mass: 340.16719519
• Monoisotopic Mass: 340.05739185
• SMILES: [n+]1(cc(ccc1)C(=O)[O-])[13C@H]1[13CH]([13C@@H]([13C@H](O1)[13CH2]OP(=O)(O)O)O)O
• Canonical SMILES: O[13CH]1[13C@H](O)[13C@H](O[13C@H]1[n+]1cccc(c1)C(=O)[O-])[13CH2]OP(=O)(O)O
• InChI: InChI=1S/C11H14NO9P/c13-8-7(5-20-22(17,18)19)21-10(9(8)14)12-3-1-2-6(4-12)11(15)16/h1-4,7-10,13-14H,5H2,(H2-,15,16,17,18,19)/t7-,8-,9?,10-/m1/s1/i5+1,7+1,8+1,9+1,10+1
• InChIKey: JOUIQRNQJGXQDC-DNZOGHTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)(^1^3C)methyl](2,3,4,5-^1^3C₄)oxolan-2-yl]-1λ^5-pyridin-1-ylium-3-carboxylate
• IUPAC Traditional name: 1-[(2R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)(^1^3C)methyl](2,3,4,5-^1^3C₄)oxolan-2-yl]-1λ^5-pyridin-1-ylium-3-carboxylate
• Synonyms: 3-Carboxy-1-(5-O-phosphono-β-D-ribofuranosyl)pyridinium-13C5 Inner Salt; 3-Carboxy-1-β-D-ribofuranosylpyridinium Hydroxide 5'-Phosphate-13C5 Inner Salt; Nicotinate Mononucleotide-13C5; Nicotinate Ribonucleotide-13C5; Nicotinic Acid Ribonucleotide-13C5; Nicotinic Acid Ribotide-13C5; Nicotinic Mononucleotide-13C5; β-NaMN-13C5; β-Nicotinic Acid Mononucleotide-13C5

Database IDs

• PubChem SID: 164231046
• PubChem CID: 71751024

CALCULATED PROPERTIES

• Acid pKa: 1.2008413
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -8.090809
• LogD (pH = 7.4): -9.207395
• Log P: -5.437405
• Molar Refractivity: 80.7223 cm^3
• Polarizability: 27.694702 Å^3
• Polar Surface Area: 160.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N429392

The labelled analogue of the nucleotide of nicotinic acid which is produced from quinolinic acid by quinolinate phosphoribosyltransferase via transfer of a phosphoribose group. It is an intermediate of nicotinic acid adenine dinucleotide (NaAD) which is t

REFERENCES

• Petrelli, R. et al.: Curr. Med. Chem., 18, 1973 (2011)
• Shibata, K. et al.: J. Chrom. B Biomed. Sci. Appl., 749, 281 (2011)
• Evans, C. et al.: BMC Chem. Biol., 10, 2 (2011)