3-carbamoyl-1-[(2R,4R,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1λ5-pyridin-1-ylium

• ChemBase ID: 175098
• Molecular Formular: C11H15N2O8P
• Molecular Mass: 334.219161
• Monoisotopic Mass: 334.05660208
• SMILES: [C@H]1(C([C@@H](O[C@@H]1COP(=O)([O-])O)[n+]1cc(ccc1)C(=O)N)O)O
• Canonical SMILES: OC1[C@@H](O)[C@H](O[C@H]1[n+]1cccc(c1)C(=O)N)COP(=O)(O)[O-]
• InChI: InChI=1S/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/t7-,8+,9?,11-/m1/s1
• InChIKey: DAYLJWODMCOQEW-GQEBFOJWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-carbamoyl-1-[(2R,4R,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 3-carbamoyl-1-[(2R,4R,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1λ^5-pyridin-1-ylium
• Synonyms: 3-(Aminocarbonyl)-1-(5-O-phosphono-β-D-ribofuranosyl)pyridinium Inner Salt; 3-Carbamoyl-1-β-D-ribofuranosylpyridinium Hydroxide, 5'-Phosphate Inner Salt; NMN; Nicotinamide Mononucleotide; Nicotinamide Ribonucleoside 5'-Phosphate; Nicotinamide Ribonucleotide; Nicotinamide Ribotide; β-D-NMN; β-NMN; β-Nicotinamide Mononucleotide

Database IDs

• CAS Number: 1094-61-7
• PubChem SID: 164231008
• PubChem CID: 71750997

CALCULATED PROPERTIES

• Acid pKa: 1.2132069
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -7.492876
• LogD (pH = 7.4): -8.585161
• Log P: -6.244348
• Molar Refractivity: 70.5857 cm^3
• Polarizability: 28.120956 Å^3
• Polar Surface Area: 166.25 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N407765

A product of the extracellular Nicotinamide phosphoribosyltransferase (eNAMPT) reaction and a key NAD+ intermediate. It ameliorates glucose intolerance by restoring NAD+ levels in HFD-induced T2D mice. It also enhances hepatic insulin sensitivity and rest

REFERENCES

• Yoshino, J. et al.: Cell Metab., 14, 528 (2011)
• Caton, P.W. et al.: Diabetologia, 54, 3083 (2011)
• Formentini, L. et al.: BIochem. Pharmacol., 77, 1612 (2011)