(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(pyridine-3-carbonyloxy)oxane-2-carboxylic acid

• ChemBase ID: 175132
• Molecular Formular: C12H13NO8
• Molecular Mass: 299.23352
• Monoisotopic Mass: 299.06411638
• SMILES: c1cncc(c1)C(=O)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@H]1O[C@H](OC(=O)c2cccnc2)[C@@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C12H13NO8/c14-6-7(15)9(10(17)18)20-12(8(6)16)21-11(19)5-2-1-3-13-4-5/h1-4,6-9,12,14-16H,(H,17,18)/t6-,7-,8+,9-,12-/m1/s1
• InChIKey: RRZLIYOEGIYOQP-LOLAFCHLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(pyridine-3-carbonyloxy)oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(pyridine-3-carbonyloxy)oxane-2-carboxylic acid
• Synonyms: β-D-Glucopyranuronic Acid 1-Nicotinate; Nicotinic Acid Acyl-β-D-glucuronide

Database IDs

• CAS Number: 24719-73-1
• PubChem SID: 164231042
• PubChem CID: 71751021

CALCULATED PROPERTIES

• Acid pKa: 2.6710873
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.9100413
• LogD (pH = 7.4): -4.822185
• Log P: -2.0425928
• Molar Refractivity: 63.4559 cm^3
• Polarizability: 25.75358 Å^3
• Polar Surface Area: 146.41 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N429260

A metabolite of Nicotinic acid.

REFERENCES

• Van Eys, J., et al.: J. Biol. Chem., 217 287 (1955)
• Wu Chang, M.L.., et al.: J. Biol. Chem., 226, 799 (1955)