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

• ChemBase ID: 155157
• Molecular Formular: C13H19N2O6P
• Molecular Mass: 330.273521
• Monoisotopic Mass: 330.09807297
• SMILES: C[C@H]1[C@H]([C@@H](O[C@@H]1COP(=O)(O)[O-])[n+]1cccc(c1)C(=O)N)C
• Canonical SMILES: C[C@@H]1[C@H](C)[C@H](O[C@H]1[n+]1cccc(c1)C(=O)N)COP(=O)(O)[O-]
• InChI: InChI=1S/C13H19N2O6P/c1-8-9(2)13(21-11(8)7-20-22(17,18)19)15-5-3-4-10(6-15)12(14)16/h3-6,8-9,11,13H,7H2,1-2H3,(H3-,14,16,17,18,19)/t8-,9+,11+,13+/m0/s1
• InChIKey: YYNOOWWEYJELSF-SEMCEJNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-carbamoyl-1-[(2R,3R,4S,5S)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dimethyloxolan-2-yl]-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 3-carbamoyl-1-[(2R,3R,4S,5S)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dimethyloxolan-2-yl]-1λ^5-pyridin-1-ylium
• Synonyms: β-NMN; β-Nicotinamide ribose monophosphate; NMN; Nicotinamide ribotide; Nicotinamide-1-ium-1-β-D-ribofuranoside 5′-phosphate; β-Nicotinamide mononucleotide

Database IDs

• CAS Number: 1094-61-7
• EC Number: 214-136-5
• MDL Number: MFCD00038748
• Beilstein Number: 3570187
• PubChem SID: 162249295; 24897645
• PubChem CID: 16219737

CALCULATED PROPERTIES

• Acid pKa: 1.2908862
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -5.028175
• LogD (pH = 7.4): -6.063495
• Log P: -3.7907608
• Molar Refractivity: 77.1691 cm^3
• Polarizability: 30.323877 Å^3
• Polar Surface Area: 125.79 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 95-100% (HPLC); 95-100% (spectrophotometric assay)
• Empirical Formula (Hill Notation): C11H15N2O8P

DETAILS

Sigma Aldrich - N3501

Other Notes
Note: This is the common form of NMN. Do not confuse it with α-NMN.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N3501.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Application
β-Nicotinamide mononucleotide (NMN) is used to study binding motifs within RNA aptamers and ribozyme activation processes involving β-nicotinamide mononucleotide (β-NMN)-activated RNA fragments.