Nicotinamide mononucleotide

Base Information

• Chemical Name: Nicotinamide mononucleotide
• CAS No.: 1094-61-7
• Deprecated CAS: 27626-81-9,1140909-84-7
• Molecular Formula: C11H15 N2 O8 P
• Molecular Weight: 334.222
• Hs Code.: 2934999090
• European Community (EC) Number: 214-136-5
• UNII: 2KG6QX4W0V
• DSSTox Substance ID: DTXSID50911152
• Wikipedia: Nicotinamide_mononucleotide
• Wikidata: Q21547155
• RXCUI: 2262276
• ChEMBL ID: CHEMBL610238
• Mol file: 1094-61-7.mol

Synonyms:Mononucleotide, Nicotinamide;Nicotinamide Mononucleotide

Chemical Property of Nicotinamide mononucleotide

Chemical Property:

• Melting Point: 166 °C(dec.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 176.06000
• Density: g/cm³
• LogP: -1.06000
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly), Water (Slightly)
• XLogP3: -3.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 334.05660244
• Heavy Atom Count: 22
• Complexity: 455

Purity/Quality:

99%,95%, ^*data from raw suppliers

b-Nicotinamide mononucleotide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C[N+](=C1)C2C(C(C(O2)COP(=O)(O)[O-])O)O)C(=O)N
• Isomeric SMILES: C1=CC(=C[N+](=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)[O-])O)O)C(=O)N
• Recent ClinicalTrials: Safety and Pharmacokinetics of Nicotinamide Mononucleotide (NMN) in Healthy Adults.
• Description: Nicotinamide mononucleotide (NMN), a product of the NAMPT reaction and a key NAD+ intermediate, ameliorates glucose intolerance by restoring NAD+ levels in HFD-induced T2D mice. NMN also enhances hepatic insulin sensitivity and restores gene expression related to oxidative stress, inflammatory response, and circadian rhythm, partly through SIRT1 activation. NMN is used for studying binding motifs within RNA aptamers and ribozyme activation processes involving β-nicotinamide mononucleotide (β-NMN)-activated RNA fragments.β-Nicotinamide mononucleotide (β-NMN) is an intermediate in the nicotinamide phosphoribosyltransferase (NAMPT)-catalyzed biosynthesis of nicotinamide adenine dinucleotide (NAD+). NAMPT mediates the condensation of nicotinamide with 5-phosphoribosyl-1-pyrophosphate to produce β-NMN. β-NMN adenyltransferase subsequently converts β-NMN to NAD+.
• Uses: 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. NMN is a nucleotide derived from ribose and nicotinamide. Niacinamide (nicotinamide,) is a derivative of vitamin B3, also known as niacin.) As a biochemical precursor of NAD+, it may be useful in the prevention of pellagra.β-Nicotinamide mononucleotide is an intermediate in the biosynthesis of nicotinamide adenine dinucleotide (NAD+). Nicotinamide phosphoribosyltransferase (Nampt) catalyzes the condensation of nicotinamide with 5-phosphoribosyl-1-pyrophosphate to generate β-NMN, which is subsequently converted to NAD+ by β-NMN adenyltransferase.At 50-100 μM, β-NMN has been used to enhance NAD biosynthesis and glucose-stimulated insulin secretion in a Nampt+/- mouse model of metabolic disease, demonstrating a role for Nampt in β cell function.Furthermore, at 500 mg/kg/day, it has been shown to ameliorate glucose intolerance in high-fat diet-induced type 2 diabetes mice by restoring NAD+ levels.

Technology Process of Nicotinamide mononucleotide

There total 45 articles about Nicotinamide mononucleotide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.27%

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside) (23111-00-4) → nicotinamide mononucleotide (1094-61-7)

Guidance literature:

With trimethyl phosphite; trichlorophosphate; at 0 ℃; for 12h; Inert atmosphere;

Reference yield: 84.2%

1-[2,3-di-O-benzoyl-5-O-(hydroxyphosphono)-β-D-ribofuranosyl]-3-carbamoylpyridinium → nicotinamide mononucleotide (1094-61-7)

Guidance literature:

With methanol; sodium methylate; at -5 ℃; for 2h; Inert atmosphere;

Reference yield: 80.0%

(3,4-dihydroxy-5-(3-(ethoxycarbonyl)pyridin-1-ium-1-yl)tetrahydrofuran-2-yl)methyl hydrogen phosphate → nicotinamide mononucleotide (1094-61-7)

Guidance literature:

With ammonia; In acetonitrile; at -5 - 5 ℃; for 1h;

upstream raw materials:

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

nicotinamide

5-phosphoribosyl-1-pyrophosphate

NAD

Downstream raw materials:

3'dNAD+

1-(β-D-ribofuranosyl)-nicotinamide

NADPH

1,4-dihydronicotinamide mononucleotide

Refernces

• 1、 Zhang, Ruo-Yu,Qin, Ye,Lv, Xiao-Qun,Wang, Pei,Xu, Tian-Ying,Zhang, Lei,Miao, Chao-Yu. "A fluorometric assay for high-throughput screening targeting nicotinamide phosphoribosyltransferase". . p. 18 - 25. Retrieved 2011.
• 2、 Mikhailopulo, I.A.,Pricota, T.I.,Timoshchuk, V.A.,Akhrem, A.A.. "Synthesis of Glycosides of Nicotinamide and Nicotinamide Mononucleotide". . p. 388 - 389. Retrieved 1981.
• 3、 Lee, Jaemoon,Churchil, Hywyn,Choi, Woo-Baeg,Lynch, Joseph E.,Roberts,Volante,Reider, Paul J.. "A chemical synthesis of nicotinamide adenine dinucleotide (NAD+)". . p. 729 - 730. Retrieved 1999.
• 4、 -. "Chemical synthesis method of NMN". Paragraph 0035; 0038; 0045-0046; 0047; 0054-0055; 0056; .... . Retrieved 2021/06/21.
• 5、 -. "Chemical synthesis method of beta-nicotinamide mononucleotide". Paragraph 0040; 0046-0049. . Retrieved 2021/11/10.